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Journal articles on the topic 'Porphyrins and derivates'

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Published: 3 June 2025

Last updated: 19 July 2025

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Chahal, Mandeep K., Nadiia Velychkivska, Whitney A. Webre та ін. "Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and β-substitution". Journal of Porphyrins and Phthalocyanines 23, № 11n12 (2019): 1184–94. http://dx.doi.org/10.1142/s1088424619501463.

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Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin. It exhibits a wide range of chromogenic responses to solvents (solvatochromism), anions and acidic media (halochromism) making it potentially useful as an analytical reagent. The chromogenic responses of OxP can be modulated by varying its chemical structure, and this is reviewed here based on the introduction of substituents at central nitrogen atoms or pyrrolic [Formula: see text]-positions. OxP and its N-alkylated derivates Bn2OxP and Bn4OxP have been used to estimate acidity in non-polar solvents. Bn2OxP can also be used to determine enantiomeric excesses of chiral substances. N-alkylation has also been used to introduce higher functional groups such as porphyrins to prepare self-assembling systems. [Formula: see text]-Substitution has been used to introduce selectivity of anion interactions including towards basic anions (fluoride, cyanide) and polyoxoanions (nitrate, perchlorate, etc.). These aspects make OxP a highly adaptable tetrapyrrole molecule for sensing and other applications.

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Egemen, Gamze, Mustafa Hayvalı, Zeynel Kılıç, A. Osman Solak, and Zafer Üstündağ. "Phosphorus-nitrogen compounds Part 17: The synthesis, spectral and electrochemical investigations of porphyrino-phosphazenes." Journal of Porphyrins and Phthalocyanines 14, no. 03 (2010): 227–34. http://dx.doi.org/10.1142/s1088424610001945.

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The reactions of unsymmetrical porphyrins (1 and 2) with Ni(OAc)2·4H2O in boiling DMF produce porphyrin complexes (3 and 4). From the reactions of free porphyrin ligands 1 and 2 with hexachlorocyclotriphosphazatriene, N3P3Cl6 , the new free porphyrino-phosphazene derivatives (5 and 6) are obtained. On the other hand, the reactions of N3P3Cl6 with porphyrin complexes (3 and 4) afford the new porphyrino-phosphazene complexes (7 and 8). In the literature there are a few examples of the porphyrino-phosphazene architectures. The structural investigations of all the compounds have been made by elemental analyses, MS, FTIR, 1H NMR, 31P NMR and UV-visible techniques. The cyclic voltammograms (CVs) are examined in acetonitrile (MeCN) containing 0.1 M tetrabutylammonium-tetrafluoroborate (TBATFB) to investigate the surface attachment properties at the glassy carbon electrode (GCE) and the influence of the presence of metal cations in the porphyrin ring.

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Mohd Radzuan, Nuur Haziqah, Zaitun Ghazali, Nurul Izzaty Hassan, Mohd Bakri Bakar, Siti Aishah Hasbullah, and Muntaz Abu Bakar. "Synthesis and Characterization of 5,15 A2-Type Porphyrin, Metalloporphyrin and Preliminary Study on Carbon Dioxide Adsorption." Sains Malaysiana 54, no. 6 (2025): 1535–49. https://doi.org/10.17576/jsm-2025-5406-09.

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Porphyrins are among the most extensively studied compounds in chemistry due to their remarkable stability, optical, and photophysical properties. In recent years, advancements in their diverse applications have driven the exploration of porphyrins with different functional groups, allowing for more specific applications. Nowadays, a greater focus is being placed on the development of materials for capturing and converting carbon dioxide (CO2) into value-added products. Despite their promising features, the application of porphyrins in carbon dioxide adsorption has been hindered by their initially low adsorption capacity compared to other traditional porous materials, such as microporous carbons and zeolites. Modifications to porphyrins, such as the introduction of diverse functional groups and the incorporation of metal centers are promising, as they may enhance the CO2 adsorption performance of porphyrin-based materials. Therefore, this study focuses on the synthesis of 5,15 A2-type porphyrin and its metalloporphyrin derivatives, along with a preliminary evaluation of synthesized porphyrin’s carbon dioxide adsorption ability. The synthesized porphyrins were characterized via nuclear magnetic resonance spectroscopy (NMR) and UV-visible spectroscopy. The yield for porphyrin varied from 23% to 35%, while metalloporphyrin achieved a yield of 99%. A preliminary study of carbon dioxide adsorption ability of porphyrin and metalloporphyrin showed that the insertion of metal into the center of porphyrin macrocyclic ring enhances the binding affinity and improves adsorption capacity. The Freundlich isotherm showed the presence of heterogeneous adsorption sites and possible multilayer adsorption of CO2 onto the porphyrin’s surface. Additionally, due to the ability of metalloporphyrin to adsorb CO2, metalloporphyrin has the potential to serve as a building block for the integration of porphyrin into hybrid materials such as metal-organic frameworks (MOFs) and covalent-organic framework (COFs), by enhancing their structural stability and CO2 performance.

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Ringot, Cyril, Naima Saad, Robert Granet, Philippe Bressollier, Vincent Sol, and Pierre Krausz. "Meso-functionalized aminoporphyrins as efficient agents for photo-antibacterial surfaces." Journal of Porphyrins and Phthalocyanines 14, no. 11 (2010): 925–31. http://dx.doi.org/10.1142/s1088424610002719.

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Anionic, neutral and cationic amino porphyrins were synthesized as precursors of photodynamic antimicrobial agents with an aim to functionalize cotton surface through 1,3,5-triazine link. Structures of porphyrin-triazine derivatives were characterized by 1H NMR, MS and UV-vis confirming the feasibility of this novel concept. Porphyrinic cotton fabrics have been developed from these derivatives, and tested in vitro against Staphylococcus aureus. These novel photodynamic surfaces showed strong and varied antimicrobial activity.

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Wenceslau, Adriana C., Guilherme L. Q. C. Ferreira, Noboru Hioka, and Wilker Caetano. "Spectroscopic studies of pyridil and methoxyphenyl porphyrins in homogeneous and Pluronic®-based nanostructured systems." Journal of Porphyrins and Phthalocyanines 19, no. 11 (2015): 1168–76. http://dx.doi.org/10.1142/s1088424615500996.

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Spectroscopic properties of Porphyrins TPyP (tetra(4-pyridil)porphyrin), TMPP (tetrakis(4-methoxypheny) porphyrin) and its zinc metaled derivatives porphyrins Zn-TPyP and Zn-TMPP respectively, were studied in homogeneous and micro heterogeneous systems, comprising nanostructured Pluronic® copolymeric micellar systems, as a promising drug delivery systems for the porphyrins investigated. Physico-chemical properties such as, hydrophobicity degree, self- aggregation in solvents of different polarities and water/ethanol mixtures (monofasic binary), as well as kinetics profile and isotherm binding, molecular organization, [Formula: see text] and relative localization in neutral micellar systems. The hydrophobic character was the key to relative drug location in the micellar systems. In homogenous solvents systems the porphyrins presented relatively high values of molar absorptivity and low values of [Formula: see text]. The K[Formula: see text] values obtained are modulated by the structure of porphyrins, state of aggregation, as well as, structure and macro molecular self-organization of copolymers. Fluorescence quenching studies have shown that porphyrins in F-127 are located in a less hydrophobic region than the porphyrins in P-123, which are located preferentially in a deeper micellar microenvironment. The zinc porphyrins showed high values of K[Formula: see text]. Thus, the association of the porphyrins with specific binding sites of micellar systems is strongly modulated by the presence of the metal coordinated to the porphyrinic ring.

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Stölzel, Ulrich, Thomas Stauch, and Ilja Kubisch. "Porphyrien." Der Internist 62, no. 9 (2021): 937–51. http://dx.doi.org/10.1007/s00108-021-01066-1.

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ZusammenfassungPorphyrien werden durch Enzymdefekte der Hämbiosynthese hervorgerufen und anhand spezifischer biochemischer Muster von Porphyrinen und deren Vorläufern in Urin, Stuhl und Blut diagnostiziert. Das jeweilige Muster der akkumulierten Porphyrine, Vorläufer und Derivate ist verbunden mit der klinischen Ausprägung, die abdominale, neurologische, psychiatrische, endokrine, kardiovaskuläre Symptome, Leberschaden und/oder Lichtempfindlichkeit der Haut umfassen kann. Klinisch werden akute und nichtakute Porphyrien unterschieden. Bei symptomatischen (klinisch aktiven), akuten hepatischen Porphyrien – hierzu gehören akute intermittierende Porphyrie, Porphyria variegata, hereditäre Koproporphyrie und Doss-Porphyrie – kommt es aufgrund einer Regulationsstörung zur Kumulation der Porphyrinvorläufer 5‑Aminolävulinsäure und Porphobilinogen. Bei den nichtakuten Formen – u. a. Porphyria cutanea tarda, erythropoetische und X‑chromosomale Protoporphyrie sowie kongenitale erythropoetische Porphyrie – führen akkumulierte Porphyrine zu Lichtempfindlichkeit (Fotodermatose) und mitunter auch zu schweren Leberschäden. Zur Therapie der Porphyrien stehen sowohl bewährte und sichere als auch innovative Optionen zur Verfügung.

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Ol’shevskaya, Valentina A., Viktoriya M. Alpatova, Nadejda V. Konovalova, Elena G. Kononova, Evgeny G. Rys, and Natalya A. Bragina. "Fluorinated derivatives of meso-(aminophenyl)porphyrins: Synthesis and some transformation." Journal of Porphyrins and Phthalocyanines 22, no. 11 (2018): 989–96. http://dx.doi.org/10.1142/s1088424618500967.

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Condensation of amino groups in 5-(4-aminophenyl)-10,15,20-triphenylporphyrin and 5,10,15,20-tetrakis(4-aminophenyl)porphyrin with pentafluorobenzaldehyde resulted in corresponding Schiff bases and was shown to be a convenient route for the preparation of fluorinated porphyrin derivatives. Compounds thus obtained were easily transformed into the corresponding amines using sodium borohydride. Fluorinated carboranyl porphyrins were prepared via the nucleophilic substitution of the para-fluorine atom of pentafluorophenyl-substituted amine porphyrin derivatives with carborane S-nucleophiles. The alternative synthetic route to the fluorinated carboranyl porphyrins included the condensation of para-carboranyl-substituted tetrafluorobenzaldehyde with corresponding meso-aminoporphyrins. All prepared porphyrins were characterized by different spectroscopic techniques such as UV-vis, IR, 1H, 11B, 19F NMR and mass spectra.

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Dinache, Andra, Simona Nistorescu, Tatiana Tozar, et al. "Spectroscopic Investigations of Porphyrin-TiO2 Nanoparticles Complexes." Molecules 28, no. 1 (2022): 318. http://dx.doi.org/10.3390/molecules28010318.

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This study presents the spectral characterization of TiO2 nanoparticles (NPs) functionalized with three porphyrin derivatives: 5,10,15,20-(Tetra-4-aminophenyl) porphyrin (TAPP), 5,10,15,20-(Tetra-4-methoxyphenyl) porphyrin (TMPP), and 5,10,15,20-(Tetra-4-carboxyphenyl) porphyrin (TCPP). UV-Vis absorption and Fourier transform infrared spectroscopy–attenuated total reflection (FTIR-ATR) spectroscopic studies of these porphyrins and their complexes with TiO2 NPs were performed. In addition, the efficiency of singlet oxygen generation, the key species in photodynamic therapy, was investigated. UV-Vis absorption spectra of the NPs complexes showed the characteristic bands of porphyrins. These allowed us to determine the loaded porphyrins on TiO2 NPs functionalized with porphyrins. FTIR-ATR revealed the formation of porphyrin-TiO2 complexes, suggesting that porphyrin adsorption on TiO2 may involve the pyrroles in the porphyrin ring, or the radicals of the porphyrin derivative. The quantum yield for singlet oxygen generation by the studied porphyrin complexes with TiO2 was higher compared to bare porphyrins for TAPP and TMPP, while for the TCPP-TiO2 NPs complex, a decrease was observed, but still maintained a good efficiency. The TiO2 NPs conjugates can be promising candidates to be tested in photodynamic therapy in vitro assays.

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Sassa, Shigeru. "Novel Effects of Heme Biological Systemst and Heme-related Compounds in Biological Systems." Current Medicinal Chemistry 3, no. 4 (1996): 273–90. http://dx.doi.org/10.2174/092986730304220302112129.

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Abstract: Heme and heme-related compounds such as porphyrins have a variety of biological and clinical activities. This review highlights some of the novel effects of these compounds in medicinal chemistry. Heme which has no photoreactive properties, can serve as the prosthetic group for various hemoproteins, or as a substrate for microsomal heme oxygenase (HO). In contrast, porphyrins have photodynamic activities but usually do not serve as substrates in biological systems. Thus, heme and heme analogues are often used to influence enzyme activities in tissues, while porphyrins by taking advantage of their photoreactive properties are used as drugs in medicine. There are four major applications of these compounds, namely the use of (i) heme in the treatment of porphyrias and hematological disorders, (ii) synthetic metalloporphyrins in the treatment of hyperbilirubinemia, (iii) metal-free porphyrins in photodynamic therapy of malignant tumors, and (iv) porphyrin derivatives as contrast reagents in radiography. Solubility, stability, pharmacokinetics, pharmacodynamics and analytical techniques are all important considerations in the medicinal chemistry of these compounds. In man and animals in vivo, the rate of synthesis and catabolism of heme, as well as disorders of heme synthesis are important in understanding pathophysiological effects of these compounds.

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Almeida, José, Maria E. Fortună, Lucia Pricop, et al. "(Aminophenyl)porphyrins as precursors for the synthesis of porphyrin-modified siloxanes." Journal of Porphyrins and Phthalocyanines 23, no. 09 (2019): 1001–12. http://dx.doi.org/10.1142/s1088424619500573.

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The present research reports the efficient synthesis of mono- and di-(aminophenyl)porphyrins and their metalation with Zn(II) using microwave irradiation. The subsequent reaction of amino-functionalized porphyrins with siloxane moieties bearing epoxy or carboxyl functional groups provided four new porphyrin-modified siloxanes. The structure of the resulting derivatives was established by 1H-NMR and MALDI-TOF-MS. The optical properties of the porphyrin chromophores were preserved, as proven by comparing the absorption and emission spectra of the initial porphyrins to those of the porphyrin-modified siloxanes.

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Ikawa, Yoshiya, Sho Katsumata, Ryuichi Sakashita, Shinobu Sato, Shigeori Takenaka, and Hiroyuki Furuta. "Water-soluble porphyrinoids as G-quadruplex binders and telomerase inhibitors." Journal of Porphyrins and Phthalocyanines 20, no. 08n11 (2016): 1041–48. http://dx.doi.org/10.1142/s108842461650053x.

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Water-soluble derivatives of three kinds of expanded porphyrins (N-fused pentaphyrin, hexaphyrin, and heptaphyrin) were synthesized and their binding ability to G-quadruplex (G4-) DNA was evaluated. The inhibitory effects on enzymatic telomere extension were also investigated together with other tetrapyrrolic porphyrinoids. While expanded porphyrins increased the melting temperature of G4-DNA more effectively than the regular porphyrins, a porphyrin isomer (N-confused porphyrin) showed the highest inhibitory effect on telomerase activity.

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YUAN, HONGPING, and L. KEITH WOO. "Synthesis and Characterization of Thiol-Derivatized Porphyrins and Metalloporphyrin complexes." Journal of Porphyrins and Phthalocyanines 01, no. 02 (1997): 189–200. http://dx.doi.org/10.1002/(sici)1099-1409(199704)1:2<189::aid-jpp23>3.0.co;2-g.

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A series of thiol-derivatized porphyrins and the corresponding cobalt and zinc complexes were synthesized from 5-(p-aminophenyl)-10,15,20-triphenylporphyrin ( H 2 TPP - NH 2), and 5α,15α-bis(o-aminophenyl)porphyrin ( H 2 DPE - ( NH 2)2). These derivatized porphyrins have a different number of thiol appendages attached via amide linkages at different locations. The thiol-derivatized porphyrins made from H 2 TPP - NH 2, H 2 TPP - NHC ( O )( CH 2) n SH ( n = 2, 4, 5, 10), have one alkyl-thiol appendage attached to the porphyrin through an amide linkage on the p-aminophenyl position. The derivatives made from H 2 DPE -( NH 2)2 have two alkyl-thiol appendages attached to the porphyrin through amide linkages on the o-aminophenyl positions on the same face of the porphyrin ring. These thiol-derivatized porphyrins are important adsorbates for the preparation of thiol–porphyrin monolayers on gold.

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Mikata, Yuji, Minako Shibata, Yasuko Baba, Toyoji Kakuchi, Misaki Nakai, and Shigenobu Yano. "Synthesis and photodynamic properties of maltohexaose-conjugated porphyrins." Journal of Porphyrins and Phthalocyanines 16, no. 11 (2012): 1177–85. http://dx.doi.org/10.1142/s1088424612501155.

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A series of porphyrin derivatives with one to four maltohexaose moieties in their meso positions have been synthesized. Zinc or free-base m-THPP (5,10,15,20-tetrakis(m-hydroxyphenyl)-porphyrin) was used as the porphyrin platform. The reaction of m-THPP with 3-iodopropyl nonadecaacetylmaltohexaoside afforded a mixture of all possible combinations of glycoconjugated porphyrins having one to four maltohexaose moieties; monoglycosylated (Ac-1), bisglycosylated (Ac-cis-2 and Ac-trans-2), triglycosylated (Ac-3), and tetraglycosylated (Ac-4) porphyrins were obtained in 11–26% yield. Removal of acetyl groups at maltohexaose moiety afforded highly water-soluble glycoconjugated porphyrins 1–4. Zinc derivatives were synthesized in a similar manner. These maltohexaose-linked porphyrins exhibit remarkable water-solublity (530 mg/mL for 4). The singlet oxygen production ability upon visible light irradiation is not affected by the maltohexaose substitution. Photo- and dark cytotoxicities of the maltohexaose-conjugated porphyrins 1–4 and Zn-1–4 were examined against a HeLa cell line, which showed that the mono-maltohexaosylated derivative (1 and Zn-1) was the most effective photosensitizer for PDT.

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Imahori, Hiroshi, and Tomokazu Umeyama. "Porphyrin-modified electrodes for solar energy conversion." Journal of Porphyrins and Phthalocyanines 13, no. 10 (2009): 1063–68. http://dx.doi.org/10.1142/s1088424609001315.

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This mini review presents our recent developments in porphyrin-modified electrodes for solar energy conversion. Various porphyrins have been assembled on nanostructured semiconducting electrodes to achieve efficient photocurrent generation. First, porphyrins have been organized with fullerenes onto semiconducting electrodes to elucidate the relationship between the molecular structures, film structures, and photoelectrochemical properties of the modified electrodes. Formation of hole and electron-transporting highways in the porphyrin/fullerene composite film led to the remarkable enhancement of photocurrent generation. Second, porphyrin-modified single-walled carbon nanotubes have also been assembled onto semiconducting electrodes. The degree of chemical functionalization by the bulky porphyrins was found to have a large impact on the photoelectrochemical properties. Third, asymmetrically π-elongated porphyrins have been successfully employed in dye-sensitized solar cells to improve the cell performance as well as the light-harvesting properties. The power conversion efficiency of the fused porphyrin cell was improved by 50% compared to the reference cell using the corresponding unfused porphyrin. Finally, carboxyquinoxalino derivatives of zinc porphyrin have been further developed to extend the concept of asymmetrically π-elongated porphyrins. The maximum power conversion efficiency of 5.2% was obtained by using 5,10,15,20-tetrakis(2,4,6-trimethylphenyl)-6′-carboxyquinoxalino[2,3-b]porphyrinatozinc(II).

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Peng, Cheng-Liang, Ping-Shan Lai, and Ming-Jium Shieh. "INFLUENCE OF SUBSTITUTIONS IN ASYMMETRIC PORPHYRINS ON INTRACELLULAR UPTAKE, SUBCELLULAR LOCALIZATION AND PHOTOTOXICITY IN HELA CELLS." Biomedical Engineering: Applications, Basis and Communications 20, no. 01 (2008): 9–17. http://dx.doi.org/10.4015/s1016237208000556.

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The asymmetric porphyrins with different substituents show various bioactivities in biomedical application. In this study, a series of asymmetric porphyrins with varying proportion of substituents, such as hydroxyphenyl and aminophenyl, were synthesized and characterized to evaluate their cell uptake, intracellular localization, cytotoxicities and phototoxicities in vitro. Among these synthesized porphyrins, 5-(4-aminophenyl)-10,15,20-tri-(4-hydroxyphenyl)-21,23H-porphyrin (porphyrin 5), which was mainly localized in mitochondria and with high quantum yields of singlet oxygen, is a potential candidate for photodynamic therapy. The effective phototoxicity of porphyrin 5 is mainly due to the higher extent in the cells and the selective mitochondria-localization. Comparing the partition coefficients of porphyrin derivatives, the best cellular uptake performs apparently with a partition coefficient (log p) ranging from about 1.7 to 1.9. In summary, higher quantum yields of singlet oxygen, and more specific mitochondrial localization of porphyrin 5 demonstrate its potential application in photodynamic therapy.

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Wang, Xia, Yu Cai, Weiqin Li, et al. "Research Progress on Serum Porphyrin and Chronic Liver Disease." Journal of Clinical and Nursing Research 6, no. 3 (2022): 221–28. http://dx.doi.org/10.26689/jcnr.v6i3.4017.

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Liver cirrhosis is an important cause of chronic liver cancer. At present, a breakthrough has been achieved in the development of chronic hepatitis C treatment, but there is no effective measure to completely cure chronic hepatitis B. Porphyrins are a class of macromolecular heterocyclic compounds formed by interconnecting the ?-carbon atoms of four pyrrole-like substituents through hypomethyl bonds. Porphyrins and their derivatives widely exist in organelles related to energy transfer in organisms. They are mainly involved in the synthesis of heme in human body. Heme is an iron-containing porphyrin compound, 15–20% of which is synthesized and utilized in the liver. Studies have found that porphyrin metabolism disorder can occur in patients with chronic liver disease. The early stage of viral hepatitis is accompanied by increased production of porphyrins and their compounds, increased levels of peripheral circulating porphyrins, porphyrin cholestasis, and biochemical changes of free porphyrins which precede the histological changes. The accumulation of serum and liver protoporphyrins and the oxidative stress can cause liver and extrahepatic damage. On the one hand, porphyrin metabolism disorder can aggravate chronic liver disease, and even progress to liver cirrhosis and liver cancer. On the other hand, chronic liver disease can also aggravate porphyrin metabolism disorder, recurrent attacks, and damage to liver and extrahepatic tissues and organs.

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Alpatova, Victoria M., Evgeny G. Rys, Elena G. Kononova, and Valentina A. Ol'shevskaya. "Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations." Beilstein Journal of Organic Chemistry 20 (April 12, 2024): 767–76. http://dx.doi.org/10.3762/bjoc.20.70.

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A carboranylporphyrin of A3B-type bearing a single pentafluorophenyl ring was prepared through the regioselective nucleophilic aromatic substitution reaction of the p-fluorine atoms in 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin with 9-mercapto-m-carborane. The reaction of this porphyrin with sodium azide led to the selective substitution of the p-fluorine atom in the pentafluorophenyl substituent with an azide functionality which upon reduction with SnCl2 resulted in the formation of the corresponding porphyrin with an amino group. Pentafluorophenyl-substituted A3B-porphyrins were studied and transformed to thiol and amino-substituted compounds allowing for the preparation of porphyrins with different reactive groups such as hydroxy and amino derivatives capable for further functionalization and conjugation of these porphyrins to other substrates. In addition, conjugates containing maleimide or biotin entities in the structure of carborane A3B-porphyrin were also synthesized based on the amino-substituted A3B-porphyrin. The structures of the prepared carboranylporphyrins were determined by UV–vis, IR, 1H, 19F, 11B NMR spectroscopic data and MALDI mass spectrometry.

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Blart, Errol, Franck Suzenet, Jean-Paul Quintard, and Fabrice Odobel. "Preparation of novel highly conjugated bis-porphyrin bridged with a polyene linker." Journal of Porphyrins and Phthalocyanines 07, no. 04 (2003): 207–13. http://dx.doi.org/10.1142/s1088424603000288.

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This paper describes the preparation of a bis free-base porphyrin and a bis-zinc porphyrin system in which the two 5,10,15-tris(3,5-ditertbutylphenyl)porphyrinyl units are connected in meso position by a tetraenic chain. The preparation of the dyad relies on the Wittig-Horner-Emmons reaction between diethyl 3-[5-[10,15,20-tris(3,5-ditert-butyl-phenyl)-porphyrinyl]] prop-2-enyl phosphonate and the aldehyde-1,3-diene[5-[10,15,20-tris(3,5-ditert-butyl-phenyl)-porphyrinyl]]. The two latter porphyrin derivatives were obtained via a Stille cross-coupling reaction between the corresponding tributyltin derivatives and the 5-iodo-10,15,20-tris(3,5-ditert-butyl-phenyl)-porphyrin. The UV-visible absorption and fluorescence spectra of the bis-porphyrin systems are measured and indicate that both the energy level and the lifetime of the porphyrin singlet excited state are reduced upon the attachment of the polyene chain to the porphyrin unit.

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Pedrosa, Leandro F., Marcos C. de Souza, Maria A. F. Faustino, et al. "Porphyrin - Phosphoramidate Conjugates: Synthesis, Photostability and Singlet Oxygen Generation." Australian Journal of Chemistry 64, no. 7 (2011): 939. http://dx.doi.org/10.1071/ch11013.

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meso-Tetrakis(pentafluorophenyl)porphyrin reacts with aminoalkylphosphoramidates to afford porphyrins substituted with one or four phosphoramidate groups in the 4-position of the meso-aryl groups. The new porphyrin derivatives show high photostability and some are better singlet oxygen generators than meso-tetrakis(1-methylpyridinium-4-yl)porphyrin, a well known good singlet oxygen producer.

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Caporaletti, Francesca, Jenifer Rubio-Magnieto, Mamadou Lo, et al. "Design of metalloporphyrins fused to imidazolium rings for binding DNA G-quadruplexes." Journal of Porphyrins and Phthalocyanines 24, no. 01n03 (2020): 340–49. http://dx.doi.org/10.1142/s1088424619501128.

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Synthesis and characterization of nickel(II) meso-tetraarylporphyrins fused to imidazolium rings across [Formula: see text],[Formula: see text]-pyrrolic positions and X-ray structure of the porphyrin where two opposed pyrrole units are fused to an imidazolium ring are presented. The interactions between these mono-, bis-, tris- and tetrakis(imidazolium) porphyrins with human telomeric DNA G-quadruplexes (G4) were investigated using UV-vis absorption spectroscopy, Circular Dichroism (CD) spectroscopy and Fluorescence Resonance Energy Transfer (FRET) melting assay. Possible binding modes between cationic porphyrins and a selected G4 sequence (d[AG3(T2AG[Formula: see text]]), and relative stabilities of porphyrin/G4 complexes are discussed. Excepting porphyrins fused to one imidazolium ring, the other derivatives interact with G4 structures and their stabilization strongly depends on the porphyrin structure (number and localization of the imidazolium rings).

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BREGADZE, VLADIMIR I., IGOR B. SIVAEV, DETLEF GABEL, and DIETER WÖHRLE. "Polyhedral boron derivatives of porphyrins and phthalocyanines." Journal of Porphyrins and Phthalocyanines 05, no. 11 (2001): 767–81. http://dx.doi.org/10.1002/jpp.544.

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The synthesis of compounds containing polyhedral boron cages and porphyrin or phthalocyanine units connected covalently in one molecule is reviewed. The importance of these compounds arises, on the one hand, from the use of polyhedral boron derivatives in neutron capture therapy for cancer; on the other hand, porphyrins and phthalocyanines are known as photosensitizers in photodynamic tumor therapy. Current interest in the binding of polyhedral boron compounds to porphyrins and phthalocyanines is due to the observation that porphyrins and phthalocyanines show improved uptake and good persistence in tissues. Medical applications of compounds containing polyhedral boron cages and porphyrin or phthalocyanine units in one molecule are briefly discussed.

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Fu, Xinliang, Demin Ren, Xiaofang Li, and Xiaolian Hu. "Synthesis of 3-cyano-N-confused porphyrin derivatives by silyl cyanide." Journal of Chemical Research 41, no. 7 (2017): 420–22. http://dx.doi.org/10.3184/174751917x14967701767076.

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3-Cyano- N-confused porphyrin derivatives were synthesised by the reaction of N-confused porphyrin with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride in moderate yield. The reaction took placed regioselectively in the 3-position carbon of the inverted pyrrole of N-confused porphyrins.

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Hill, Jonathan P., Wim Van Rossom, Shinsuke Ishihara, et al. "Unexpected but convenient synthesis of soluble meso-tetrakis(3,4-benzoquinone)-substituted porphyrins." Journal of Porphyrins and Phthalocyanines 18, no. 03 (2014): 173–81. http://dx.doi.org/10.1142/s1088424613501071.

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A new route to 3,4-benzoquinone-substituted porphyrins is reported. In attempted nitration reactions on the copper(II) or nickel(II) complexes of 5,10,15,20-tetrakis(3,5-di-t-butyl-4-hydroxyphenyl)porphyrin using lithium nitrate in acetic anhydride-acetic acid/chloroform no nitration products could be detected with the main products being the corresponding complexes of 5,10,15,20-tetrakis(3,4-dioxo-5-t-butylcyclohexa-1,5-dienyl)porphyrin. These o-quinone-substituted porphyrins are available in reasonable yield (> 50%), their synthesis is simple and they are of good solubility. The electrochemical and spectroelectrochemical properties of representative o-quinone-substituted Cu ( II ) and Ni ( II ) porphyrin derivatives are also reported.

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Zhang, Shaowei, Xinliang Fu, Demin Ren, Xiaofang Li, Leilei Yang, and Xianyong Yu. "Synthesis of 3-Cyano-21-Nitro-N-Confused Porphyrin Derivatives by Isoamyl Nitrite." Journal of Chemical Research 41, no. 9 (2017): 517–19. http://dx.doi.org/10.3184/174751917x15027989008991.

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The 3-cyano-21-nitro- N-confused porphyrin derivatives were synthesised by the nitration reaction of 3-cyano- N-confused-porphyrin with isoamyl nitrite at room temperature in moderate yield. The reaction took placed regioselectively in 21-position carbon of inverted pyrrole of N-confused porphyrins.

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Barkhudaryan, Vigen G., and Gayane V. Ananyan. "Development of viscometric methods for studying the interaction of various porphyrins with DNA. Part III: Meso-tetra-(3N-alylpyridyl)porphyrin and its Cu-, Co- and Zn-containing derivatives." Journal of Porphyrins and Phthalocyanines 21, no. 02 (2017): 110–15. http://dx.doi.org/10.1142/s1088424617500122.

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Present research continues the development of viscometry method for studying porphyrin–DNA interactions.Water soluble cationic meso-tetra-(3[Formula: see text]-alylpyridyl) porphyrin (H2TAlPyP3) and its Cu-, Co- and Zn-containing derivatives were studied using UV-vis absorption spectroscopy and viscometry in order to clarify the effect of chemical structure (presence of double bond in structure of a side radical) of porphyrins and ability to affect the DNA structure. Their binding constant ([Formula: see text] and stoichiometry ([Formula: see text] were determined based on the absorbance spectra for each DNA–porphyrin complex. The results were compared with results of previously conducted similar studies with meso-tetra-(3[Formula: see text]-hydroxyethylpyridyl) porphyrins. It was shown, that the planar porphyrins H2TAlPyP3 and CuTAlPyP3 interact with DNA predominantly by intercalation at low relative concentrations of [Formula: see text](([Formula: see text] [Formula: see text] [Porphyrin]/[DNA])) and by external binding mode at high values of [Formula: see text], whereas the change of chemical structure of peripheral radicals of porphyrins does not absolutely affect on the mechanism of interaction of outside binders CoTAlPyP3 and ZnTAlPyP3 with DNA.

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M., RAVIKANTH, REDDY DAMODAR, and K. CHANDRASHEKAR T. "Short Chain Basket Handle Porphyrins : Ground and Excited State Dynamics." Journal of Indian Chemical Society Vol. 70, Nov-Dec 1993 (1993): 1023–34. https://doi.org/10.5281/zenodo.5958326.

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Department of Chemistry, Indian Institute of Technology, Kanpur-208 016 Manuscript received 31 August 1993 The effect of porphyrin ring distortion on the ground and excited state dynamics of short chain basket handle porphyrins has been investigated. The covalent attachment of phenyl ring of meso-5,10,15,20-tetraphenylporphyrin (Hz TPP) by short bridging groups of varying nature and length induces distortion in the porphyrin ring. The optical absorption bands and emission bands exhibit significant red-shifts with reduction in intensity relative to corresponding planar porphyrin due to ring distortion. On protonation both optical and emission bands experience blue-shift due to lack of expected resonance interaction. Metallation does not alter the degree of distortion. The ZnII derivatives showed emission from both S1 and S2 excited state with quenching of fluorescence. Redox potential data suggest easier oxidations and harder reductions both in the ground and first singlet excited states relative to corresponding planar porphyrins. Zero field splitting parameters D and E of basket handle porphyrins evaluated from photoexcited triplet esr show small but significant differences attributed to distortion of the porphyrin plane. The calculated structures reveal the expected distortion in the porphyrin plane caused by short bridging groups and offers an explanation for the unusual spectral and electrochemical shifts observed in basket handle porphyrins relative to planar porphyrins.

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Komath, Sneha Sudha, Kancheenadham Bhanu, Bhaskar G. Maiya, and Musti J. Swamy. "Binding of Porphyrins by the Tumor-Specific Lectin, Jacalin [Jack Fruit (Artocarpus integrifolia) Agglutinin]." Bioscience Reports 20, no. 4 (2000): 265–76. http://dx.doi.org/10.1023/a:1026440907227.

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Jacalin (Artocarpus integrifolia agglutinin) specifically recognizes thetumor-associated T-antigenic disaccharide structure, Galγ13GalNAc. Porphyrins and their derivatives are currently used asphotosensitizers in photodynamic therapy to treat malignant tumors. In thisstudy, the interaction of several free base porphyrins and their metalderivatives with jacalin is investigated by absorption and fluorescencespectroscopy. Each lectin subunit was found to bind one porphyrin moleculeand the association constants were estimated to be in the range of 2.4 × 103M−1 to 1.3 × 105M−1 at room temperaturefor the interaction of different porphyrins with jacalin. These values arein the same range as those obtained for the interaction of monosaccharidesto jacalin. Both free lectin and lectin saturated with the specificsaccharide were found to bind different porphyrins with comparable bindingstrength indicating that porphyrin binding takes place at a site differentfrom the sugar binding site. Further, both anionic and cationic porphyrinswere found to interact with the lectin with comparable affinity, clearlyindicating that the charge on the porphyrin does not play any role in thebinding process and that most likely the interaction is mediated byhydrophobic forces. These results suggest that jacalin and other lectins maypotentially be useful for targeted delivery of porphyrins to tumor tissuesin photodynamic therapy.

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Buczyńska, Joanna, Agnieszka Gajewska, Aleksander Gorski, et al. "Synthesis and Photostability of Cyclooctatetraene-Substituted Free Base Porphyrins." Chemistry 3, no. 1 (2021): 104–15. http://dx.doi.org/10.3390/chemistry3010008.

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A series of free base meso-tetraarylporphyrins functionalized with substituents containing one, two, and four cyclooctatetraene (COT) moieties have been obtained and characterized by spectral and photophysical studies. Three COT-free porphyrins served as reference compounds. COT is a triplet quencher, well-known to enhance the photostability of several, but not all, fluorophores. In the case of porphyrins, substitution with COT improves photostability in zinc derivatives, but for free bases, the effect is the opposite. We show that placing the COT moiety further from the free base porphyrin core enhances the photostability when the COT group lies in the direct vicinity of the macrocycle. The quantum yields of photobleaching inversely correlate with porphyrin oxidation potentials. An improvement in photostability in both COT-containing and COT-free porphyrins can be achieved by screening the porphyrin core from oxygen by switching from tolyl to mesityl substituents. This leads to a decrease in the photobleaching quantum yield, even though triplet lifetimes are longer. The results confirm the involvement of oxygen in the photodegradation of porphyrins.

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Ol’shevskaya, Valentina A., Elena G. Kononova, and Andrei V. Zaitsev. "Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization." Beilstein Journal of Organic Chemistry 15 (November 13, 2019): 2704–9. http://dx.doi.org/10.3762/bjoc.15.263.

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Maleimide-containing fluorinated porphyrins and chlorins were prepared based on the reaction of Zn(II) or Ni(II) complexes of 5,10,15,20-tetrakis(4-amino-2,3,5,6-tetrafluorophenyl)porphyrin and chlorin with maleic anhydride. Porphyrin maleimide derivatives were also prepared by the reaction of 5,10,15,20-tetrakis(4-azido-2,3,5,6-tetrafluorophenyl)porphyrinato Zn(II) or Ni(II) with N-propargylmaleimide via the CuAAC click reaction to afford fluorinated porphyrin–triazole–maleimide conjugates. New maleimide derivatives were isolated in reasonable yields and identified by UV–vis, 1H NMR, 19F NMR spectroscopy and mass-spectrometry.

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James, B. R., G. G. Meng, J. J. Posakony, J. A. Ravensbergen, C. J. Ware, and K. A. Skov. "Porphyrins and Metalloporphyrins: Potential Hypoxic Agents." Metal-Based Drugs 3, no. 2 (1996): 85–89. http://dx.doi.org/10.1155/mbd.1996.85.

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Synthetic water-soluble porphyrins and their metalloporphyrin derivatives with Co(III), Cu(II), Ru(II) and Pt(II), containing various functional groups within the meso-positions of the porphyrin, were synthesised and evaluated as hypoxic agents, especially as cytotoxins and radiosensitisers. Cobalt complexes of the porphyrins containing positively charged methylpyridinium groups showed selective toxicity toward hypoxic Chinese Hamster Ovary (CHO) cells. The Co(III) complexes of the cationic and the anionic porphyrins are all weak radiosensitisers toward hypoxic cells, the highest sensitisation enhancement ratio (SER = 1.22, at 50 μM) being with a porphyrin complex containing a cis-arrangement of two nitro and two methylpyridinium meso-substituents. A copper complex of a tetracationic porphyrin showed slight radiosensitisation activity with an SER value of about 1.1. The other metalloporphyrins showed no hypoxic selectivity or radiosensitisation activity. In total, over 50 porphyrin free bases have been synthesised, of which half are water-soluble and have been metallated; thus, the chemistry is now in place for further development of water-soluble hypoxic agents.

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Intrieri, Daniela, Daniela Maria Carminati, and Emma Gallo. "Recent advances in C–H bond aminations catalyzed by ruthenium porphyrin complexes." Journal of Porphyrins and Phthalocyanines 20, no. 01n04 (2016): 190–203. http://dx.doi.org/10.1142/s1088424616500383.

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This review deals with the use of ruthenium porphyrin complexes to catalyze hydrocarbon aminations. This class of versatile porphyrin catalysts are able to activate different nitrogen sources, such as iminoiodinanes and organic azides, and promote the synthesis of a variety of aza-derivatives. Many synthetic procedures have been discussed as well as catalytic mechanisms involved in order to give an overview on the use of ruthenium porphyrins to promote nitrene transfer reactions yielding aminated derivatives.

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Uoyama, Hiroki, Takahiro Takiue, Kazuyuki Tominaga, Noboru Ono, and Hidemitsu Uno. "Synthesis, structures, and properties of BCOD-fused porphyrins and benzoporphyrins." Journal of Porphyrins and Phthalocyanines 13, no. 01 (2009): 122–35. http://dx.doi.org/10.1142/s108842460900022x.

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Bicyclo[2.2.2]octadiene (BCOD)-fused porphyrins with no other substituents were prepared by [2 + 2] and [3 + 1] porphyrin syntheses from ethanodihydroisoindole derivatives in fairly good yields. Thermal retro-Diels-Alder reactions of BCOD-fused porphyrins gave the corresponding benzoporphyrins with no substituent in quantitative yields. Their UV-vis spectra and crystal structures were carefully examined in terms of π-system expansion of the porphyrin ring current. In the cases of monobenzo- and adj-dibenzo-porphyrins, a single Soret band in their UV-vis spectra and no bond alteration in the benzene rings of their crystal structures were observed, while the split Soret bands and the obvious bond alteration in their benzene rings were recorded in the case of opp-dibenzoporphyrin.

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Zakharov, M. S., and Y. V. Tertyshnaya. "Porphyrins and porhyrin polymers: synthesis, structural features, prospects of application." Журнал органической химии 59, no. 7 (2023): 835–57. http://dx.doi.org/10.31857/s0514749223070017.

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The review covers works on the synthesis of porphyrins, including amphiphilic star-shaped ones, which are attracting more and more attention of synthetic scientists. The potential of various types of porphyrins, metalloporphyrins and their derivatives as photosensitizers in photodynamic therapy is discussed. The relationship between the structure of porphyrins and their antimicrobial activity is shown. Polymer-porphyrin systems based on biodegradable polyesters and tetraphenylporphyrins immobilized in their matrix are considered as promising composite materials with bactericidal properties.

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Gunter, MJ, та BC Robinson. "Purpurins Bearing Functionality at the 6,16-meso-Positions: Synthesis From 5,15-Disubstituted meso-[β-(Methoxycarbonyl)vinyl]porphyrins". Australian Journal of Chemistry 43, № 11 (1990): 1839. http://dx.doi.org/10.1071/ch9901839.

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Porphyrins bearing p-X-phenyl substituents (X=Me, OH, OTs , NMe2, NO2) at the 5,15-meso-positions have been synthesized. meso-Formylation of the nickel derivatives produced the derivatives (4), (12), (17) and (23) which show atypical broadened Soret and Q-band absorptions, the latter at 570-750 nm. The optical and n.m.r. spectra of the corresponding free base monoformyl derivatives also indicate electronic perturbations of the porphyrin rr -system. Wittig reactions with ( methoxycarbonylmethylene ) triphenylphosphorane, followed by demetallation, resulted in the meso-acrylate porphyrins (8), (14), (19) and (25), which also exhibit unusual electronic spectra consistent with a distortion of the macrocyclic ring current. The p-dimethylaminophenyl derivative (14) also shows protonation-dependent spectra indicating a quinomethene structure. The meso-acrylate porphyrins were efficiently converted into type A purpurins under basic conditions. Type B purpurins were also formed, and the relative yields of types A and B are temperature and solvent dependent, but independent of the presence of oxygen. These results are in contrast to those for the formation of octaethylpurpurin derivatives; likewise, no evidence of a purpurin - porphyrin equilibrium was observed for these compounds. In the presence of oxygen and strong visible light the meso-formyl-2- ( methoxyoxalyl ) chlorins are formed. The electronic spectra of the purpurins are typified by strong absorptions in the red region of the spectrum; the p- dimethylaminophenyl derivative (27) also exhibits a solvent-dependent spectrum, which is explained in terms of a dimethylaminoquinomethene tautomerism. The purpurins and porphyrin derivatives have potential application in photodynamic cancer therapy.

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Horn, Sabine, Katja Dahms, and Mathias O. Senge. "Synthetic transformations of porphyrins – Advances 2004-2007." Journal of Porphyrins and Phthalocyanines 12, no. 10 (2008): 1053–77. http://dx.doi.org/10.1142/s108842460800042x.

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Recent developments in the synthesis and transformation of porphyrins and their derivatives are presented. In connection with the Fifth International Conference on Porphyrins and Phthalocyanines (ICPP-5) a survey of current method developments and reactivity studies is made. The review focuses on synthetic advances in porphyrin chemistry. A brief survey of important developments covers selectively the literature from 2004 to late 2007.

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Wang, Hong, Yi Hu, Michael Thomas, Ajyal Alsaleh, and Francis D'Souza. "(Invited) Pi-Extended Porphyrins: Synthesis, Functionalization and Applications in Dye-Sensitized Solar Cells." ECS Meeting Abstracts MA2022-01, no. 13 (2022): 903. http://dx.doi.org/10.1149/ma2022-0113903mtgabs.

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pi-Extended porphyrins are of broad interest due to their unique combination of photophysical, optoelectronic, and physicochemical properties, and their potential applications in many areas ranging from biomedicine to organic electronics.1,2 In this talk, three series of beta-functionalized push-pull pi-extended porphyrins as sensitizers for dye-sensitized solar cells will be presented.3-5 Our studies show significant push-pull effects for these porphyrins. DFT calculations suggest that the inclusion of ethynylphenyl bridge between the donating group and the porphyrin core significantly segregate the frontier orbitals. It has also been found that dimethylaminophenyl group cause dye decomposition on solar cells. To solve the dye degradation problem, porphyrin dyes with tertiary arylamine groups serving as the donor groups were prepared. Our studies show that tertiary arylamine groups are able to stabilize the dyes adsorbed on the solar cells. Their photovoltaic performances were tested in dye-sensitized solar cells. In this talk, the synthesis and characterization of pentacene-fused (linearly conjugated) and pentaquinone-fused (cross-conjugated) porphyrin oligomers will also be presented.6 These pentacene-fused porphyrins are much more stable than their corresponding pentacene derivatives. The electronic absorption spectra and transit spectroscopy of these porphyrins indicate highly interactive multiple p-systems. The electronic and optical properties of these p-extended porphyrins were measured using UV-Vis spectroscopy, life-time and steady state fluorescence spectroscopy, and cyclic voltammetry. DFT calculations were also performed for these porphyrins.

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Karapetyan, Nelli H., Lusya V. Torosyan, Gayane V. Ananyan, and Rafael E. Muradyan. "DNA damage and anti-tumor activity induced by Zn, Ag and Co containing meso- tetra(4-N-oxyethylpyridyl)porphyrins in vivo." Journal of Porphyrins and Phthalocyanines 14, no. 04 (2010): 349–53. http://dx.doi.org/10.1142/s1088424610002100.

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In the present study, the activity of the new water-soluble cationic meso-tetra(4-N-oxyethylpyridyl)porphyrin and its Zn , Ag and Co metal derivatives as anti-tumor agents was explored. The tumor was induced by 7,12-dimethylbenz[a]antracene (DMBA) on rats of Wistar strain. The levels of DNA damage induced by porphyrins T4OEPyP , AgT4OEPyP , ZnT4OEPyP and CoT4OEPyP in tumor tissue were analyzed. Thermodynamic parameters of DNA were investigated by thermal melting method and differential scanning microcalorimetry to understand the differences in DNA structure of three types of rat: normal, dieseased with tumor, and treated by porphyrins. Agarose gel electrophoresis method was used to detect porphyrin-induced apoptosis or necroses. Based on the data obtained, we concluded that the investigated ZnTOEPyP and AgTOEPyP porphyrins have more anti-tumor activity than CoTOEPyP and TOEPyP .

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Montaseri, Hanieh, Cherie Ann Kruger, and Heidi Abrahamse. "Recent Advances in Porphyrin-Based Inorganic Nanoparticles for Cancer Treatment." International Journal of Molecular Sciences 21, no. 9 (2020): 3358. http://dx.doi.org/10.3390/ijms21093358.

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The application of porphyrins and their derivatives have been investigated extensively over the past years for phototherapy cancer treatment. Phototherapeutic Porphyrins have the ability to generate high levels of reactive oxygen with a low dark toxicity and these properties have made them robust photosensitizing agents. In recent years, Porphyrins have been combined with various nanomaterials in order to improve their bio-distribution. These combinations allow for nanoparticles to enhance photodynamic therapy (PDT) cancer treatment and adding additional nanotheranostics (photothermal therapy—PTT) as well as enhance photodiagnosis (PDD) to the reaction. This review examines various porphyrin-based inorganic nanoparticles developed for phototherapy nanotheranostic cancer treatment over the last three years (2017 to 2020). Furthermore, current challenges in the development and future perspectives of porphyrin-based nanomedicines for cancer treatment are also highlighted.

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Rudine, Alexander B., Nicholas U. Day, Xisen Tian, Chang Lee, Keith E. James, and Carl C. Wamser. "Aminophenyl/carboxyphenylporphyrins as sensitizers for dye-sensitized solar cells." Journal of Porphyrins and Phthalocyanines 20, no. 08n11 (2016): 1217–23. http://dx.doi.org/10.1142/s1088424616500565.

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A series of tetraphenyl meso-substituted porphyrins with either p-amino or p-carboxy substituents has been studied as dyes for standard dye-sensitized solar cells (DSSCs). The porphyrins with greater numbers of amino groups generally show greater efficiency, primarily due to higher photocurrents; open-circuit voltage and fill factors are comparable. The most efficient sensitizer was the trans disubstituted zinc porphyrin, with an overall solar energy conversion efficiency of 5.66%, slightly higher than the triamino zinc porphyrin at 5.18%. The improved efficiency is attributed to the well known push–pull effect in porphyrinsensitized DSSCs with electrondonating groups opposite to the electronwithdrawing anchoring (carboxy) groups. It is suggested that porphyrin derivatives with cis diaminophenyl groups show somewhat diminished efficiency due to difficulties with regeneration of the dye from its oxidized form.

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Ramaiyah, Yasothaa, Mohd Bakri Bakar, and Muntaz Abu Bakar. "Elucidating the Binding Affinity of Meso Porphyrin Derivatives with Bcl-2 through Synthesis and Molecular Docking Analysis." Sains Malaysiana 52, no. 11 (2023): 3325–42. http://dx.doi.org/10.17576/jsm-2023-5211-22.

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Reversing multi-drug resistance in a clinical setting remains a formidable issue to date. Porphyrin has high efficiency to conjugate with chemotherapy drugs and effectively deliver within the nucleus of cancer cells which helps in lowering side effect to normal cells. As compared to naturally occurring beta-substituted porphyrins, synthetic meso-substituted porphyrins have numerous benefits. An extensive variety of substituents have been developed with porphyrins. There are eight new porphyrin derivatives synthesised in this research compounds 14-21 which differ from one size to another using Sonogashira and Suzuki coupling techniques. Sonogashira coupling method undergoes a reaction between alkyne terminal sp hybridized carbon and vinyl halide’s sp2 carbon in the presence of a Palladium catalyst. Furthermore, Suzuki coupling method has been an effective method in conjugation of aryl halides and borylated porphyrins. The synthesized new compounds were characterized by ultra-violet spectroscopy (UV-Vis), high resolution mass spectrometer (HRMS) and nuclear magnetic resonance (NMR) to confirm successful formation of all new compounds. The docking analysis was performed for compound 14-21. Compounds 16 and 18 showed the greater binding mode at the Bcl-2 protein pocket regards free or metal substituted porphyrin with longer linker chain and less bulky compared to compounds 17 and 19. This study could discover the structure of porphyrin that affects accumulation in cancer cells that potentially transmissible to target tumour.

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Povolotskiy, A. V., O. S. Smirnova, D. A. Soldatova, and D. A. Lukyanov. "Fluorescent ratiometric thermometers based on dyads of tetraphenyl porphyrin and zinc-metallated tetraphenyl porphyrin." Известия Российской академии наук. Серия физическая 87, no. 11 (2023): 1631–36. http://dx.doi.org/10.31857/s0367676523702824.

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Porphyrins and their derivatives are known for their ability to emit two fluorescence bands. We presented the results of the investigation of the intensity ratio dependence for these bands on temperature in the range of 25–75°C for non-metaled and metal-plated with zinc porphyrins, as well as porphyrin dyads in solutions of 1,2-dichloroethane. A comparative analysis of thermometric parameters of these molecules was carried out.

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Vzorov, Andrei N., Dabney W. Dixon, Jenna S. Trommel, Luigi G. Marzilli, and Richard W. Compans. "Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins." Antimicrobial Agents and Chemotherapy 46, no. 12 (2002): 3917–25. http://dx.doi.org/10.1128/aac.46.12.3917-3925.2002.

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ABSTRACT We have evaluated the anti-human immunodeficiency virus (HIV) activity of a series of natural and synthetic porphyrins to identify compounds that could potentially be used as microbicides to provide a defense against infection by sexually transmitted virus. For assays we used an epithelial HeLa-CD4 cell line with an integrated long terminal repeat-β-galactosidase gene. For structure-activity analysis, we divided the porphyrins tested into three classes: (i) natural porphyrins, (ii) metallo-tetraphenylporphyrin tetrasulfonate (metallo-TPPS4) derivatives, and (iii) sulfonated tetra-arylporphyrin derivatives. None of the natural porphyrins studied reduced infection by more than 80% at a concentration of 5 μg/ml in these assays. Some metal chelates of TPPS4 were more active, and a number of sulfonated tetra-aryl derivatives showed significantly higher activity. Some of the most active compounds were the sulfonated tetranaphthyl porphyrin (TNapPS), sulfonated tetra-anthracenyl porphyrin (TAnthPS), and sulfonated 2,6-difluoro-meso-tetraphenylporphine [TPP(2,6-F2)S] and its copper chelate [TPP(2,6-F2)S,Cu], which reduced infection by 99, 96, 94, and 96%, respectively. Our observations indicate that at least some of these compounds are virucidal, i.e., that they render the virus noninfectious. The active compounds were found to inhibit binding of the HIV type 1 gp120 to CD4 and also to completely inhibit the ability of Env proteins expressed from recombinant vectors to induce cell fusion with receptor-bearing target cells. These results support the conclusion that modified porphyrins exhibit substantial activity against HIV and that their target is the HIV Env protein.

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Ostapko, Jakub, Joanna Buczyńska, Maria Pszona, Patrycja Kowalska, and Jacek Waluk. "Synthesis, spectroscopy, and photophysics of porphyrins attached to gold nanoparticles via one or two linkers." Journal of Porphyrins and Phthalocyanines 18, no. 08n09 (2014): 686–97. http://dx.doi.org/10.1142/s1088424614500424.

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Four new meso-tetraphenylporphyrin derivatives were prepared, singly and doubly substituted with thiocarbamate and thioacetate groups. These compounds were subsequently attached to gold nanoparticles suspended in chloroform. Very different kinetics of the attachment were revealed; the process was much faster for the thiocarbamate derivatives. Spectral, photophysical, and scanning electron microscopy studies revealed large differences in the morphology of the gold–porphyrin systems. The porphyrins with one linker attach to single nanoparticles, whereas the dual linker derivatives induce formation of aggregates, characterized by readily detectable Raman signals. A "hot-spot" type structure is proposed for the latter, with the porphyrin bridging two gold nanoparticles.

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Costa, Joana I. T., Andreia S. F. Farinha, Filipe A. Almeida Paz, and Augusto C. Tomé. "A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine." Molecules 24, no. 17 (2019): 3177. http://dx.doi.org/10.3390/molecules24173177.

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A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)–PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6–PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.

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Cuesta, Virginia, Maida Vartanian, Pilar de la Cruz, Ganesh D. Sharma, and Fernando Langa. "The Influence of the Central Metal Ion on the Electronic and Photovoltaic Properties of Metalloporphyrins [M= Zn(II), Ni(II), Cu(II), Au(III)] Systems." ECS Meeting Abstracts MA2023-01, no. 15 (2023): 1395. http://dx.doi.org/10.1149/ma2023-01151395mtgabs.

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Although the pioneering use of porphyrins in organic solar cells (OSCs) was disappointing as reported efficiencies were very low, the situation has changed over the last five years as Zn-porphyrins with ABAB structures linked to acceptor units through triple bonds have been applied as donors resulting in efficiencies of up to 12% in binary OSCs and more than 15% in ternary OSCs. The optical and electrochemical properties of porphyrins can be adjusted by molecular design and functionalization on the b or meso positions of the porphyrin ring as well as by introduction of different central metal ions. The choice of the centrally bounded metal cation within the porphyrin core plays an important role in the electronic properties allowing the modulation of the frontier orbital levels and thereby use the porphyrin-based molecule as donor or acceptor component of the device. Due to the high HOMO level of Zn-Porphyrin derivatives, the Voc of OSCs using this family of compounds are lower than 0.9 V limiting the PCE of devices. We have described that Ni-porphyrins derivatives allow the design of OSCs with voltage higher than 1V. These systems present slightly higher optical bandgaps but the deeper highest occupied molecular orbital (HOMO) energy level make available to reach good PCE values of the solar devices. While porphyrins and their derivatives have been extensively used as donor component in the BHJ active layer of OSCs, the investigation of porphyrin-based materials as electron acceptor is very limited. Recently, we designed a new A2-D-A1-D-A2 non fullerene small molecule acceptor (NFSMA) with broad absorption up to 920 nm and a great absorption coefficient where A1 core is Au(III) porphyrin. This molecule, when used in OSC with a polymer donor yielded a PCE=9.24%. Nevertheless, the use of other central metals such as Cu(II) in the porphyrin core has been scarcely used in OSCs, the studied devices presented low efficiencies (≤ 3%). These outcomes demonstrated that metalloporphyrins, which is different from Zn-porphyrins, also have great potential for the design of NFSMAs for efficient OSCs. Also, we have studied A-π-D-π-A small molecules based on Cu(II) Porphyrin, scarcely used in OSCs, presenting an ambipolar behaviour, as donor and as acceptor. Here, I´ll present our recent work in design, synthesis, and application of porphyrin-based small molecules with different central metal for highly efficient OSCs. References V. Cuesta, M. Vartanian, P. de la Cruz, R. Singhal, G. D. Sharma and F. Langa. J. Mater. Chem. A, 2017, 5, 1057. S. Arrechea, A. Aljarilla, P. de la Cruz, M. K. Singh, G. D. Sharma and F. Langa. J. Mater. Chem. C, 2017, 5, 4742. M. Vartanian, R. Singhal, P. de la Cruz, S. Biswas, G. D. Sharma and F. Langa. ACS Appl. Energy, Mater., 2018, 1, 1304. M. Vartanian, P. de la Cruz, F. Langa, S. Biswas and G. D. Sharma. Nanoscale, 2018, 10, 12100. M. Vartanian, R. Singhal, P. de la Cruz, G. D. Sharma and F. Langa. Chem. Commun., 2018, 54, 14144. V. Cuesta, R. Singhal, P. de la Cruz, G. D. Sharma and F. Langa. ACS Appl. Mater. Interfaces, 2019, 11, 7216. Cuesta, R. Singhal, P. de la Cruz, G. D. Sharma and F. Langa, ChemSusChem, 2021, 14, 3439. H. Dahiya, V. Cuesta, P. de la Cruz, F. Langa and G. D. Sharma ACS Appl. Energy Mater., 2021, 4, 4498. Figure 1

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Dekkiche, Hervé, Yoshihiro Kikkawa, Lydia Karmazin, Christophe Jeandon, and Romain Ruppert. "Synthesis of porphyrins bearing alkynyl- or arylalkynyl-meso-groups." Journal of Porphyrins and Phthalocyanines 20, no. 01n04 (2016): 292–301. http://dx.doi.org/10.1142/s108842461650005x.

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The synthesis of new porphyrins bearing external coordination sites and long alkyl chains is described. In particular, the possibility to use the Sonogashira coupling to introduce long alkynyl chains and the synthetic pathway to obtain these compounds is detailed. Two crystal structures of these new porphyrin derivatives were obtained. The synthesis of porphyrin dimers linked by a palladium(II) ion is also reported and some electronic consequences presented.

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Galindev, Oyunbileg, Narangerel Badraa, and Young Key Shim. "Synthesis of methyl pyropheophorbide-a pyrazole derivatives and their in vitro cell viabilities on A549 cells." Journal of Porphyrins and Phthalocyanines 11, no. 12 (2007): 829–35. http://dx.doi.org/10.1142/s1088424607000953.

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Porphyrins and chlorins containing acetylacetone residues on the peripheral substituents are known to readily react with hydrazine derivatives to form porphyrin and chlorin derivatives possessing a pyrazole moiety. In this study, we have carried out the synthesis of methyl pyropheophorbide-a derivatives containing a pyrazole moiety on its peripheral position. Moreover, we have examined a preliminary in vitro effect of these new derivatives on A549 cancer cell in photodynamic therapy.

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Carlucci, Lucia, Gianfranco Ciani, Simona Maggini, et al. "Synthesis and characterization of new tetra-substituted porphyrins with exo-donor carboxylic groups as building blocks for supramolecular architectures: Catalytic and structural studies of their metalated derivatives." Journal of Porphyrins and Phthalocyanines 14, no. 09 (2010): 804–14. http://dx.doi.org/10.1142/s1088424610002641.

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We report herein the synthesis of the porphyrins 5,10,15,20-tetrakis(4-carboxybiphenyl)-porphyrin (H2TCBP) and 5,10,15,20-tetrakis(4-carboxy-2,6-dimethylbiphenyl)porphyrin (H2TCDMBP) bearing diphenyl units on meso-positions, and of their cobalt and silver derivatives. The silver complexes of H2TCDMBP and of H2TCPP ( H2TCPP = 5 ,10,15,20-tetrakis(4-carboxyphenyl)porphyrin) were investigated by X-ray crystallography and their supramolecular organization elucidated. Co(TCBP) was reacted with copper formate, yielding a polymeric compound that showed a catalytic activity in the benzylic amination of hydrocarbons using arylazide as aminating agent.

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Jaafar, Mohammed Thamer, Luma Majeed Ahmed, and Rahman Tama Haiwal. "Synthesis, Characterization, and Electrochemical Study of Novel Porphyrin Derivatives as Corrosion Inhibitors for Carbon Steel in HCl Solutions." Indonesian Journal of Chemistry 24, no. 2 (2024): 379. http://dx.doi.org/10.22146/ijc.87682.

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This study involves the synthesis of some porphyrins derivatives, these are termed as 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N-(6-aminoacridin-3-yl)benzamide) (3a), 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N-(5-methoxybenzo[d]thiazol-2-yl)benzamide) (3b), 4,4'-(10,20-bis(3-hydroxyphenyl)porphyrin-5,15-diyl)bis(N-(6-aminoacridin-3yl)benzamide) (5a), and 4,4'-(10,20-bis(3-hydroxyphenyl)porphyrin-5,15-diyl)bis(N-(benzo[d]thiazol-2-yl)benzamide) (5b). These derivatives were synthesized using open circuit potential (OCP) and potentiodynamic polarization (PDP) in 0.1 M HCl solution methods. These derivatives were characterized using nuclear magnetic resonance (1H- and 13C-NMR) spectroscopy, mass spectra (ESI), and micro elemental analysis (CHN). The activity of these synthesized materials was investigated as a corrosion inhibitor using carbon steel (CS) as a model for corroded materials. The obtained results showed that the synthesized porphyrins derivatives were effective corrosion inhibitors to 0.1 M HCl solution for CS. In the case of the derivative 3a, a maximum inhibition efficiency (IE%) was recorded and it was around 74%. The derivative 3b showed an IE% of around 68.11%, while the %IE of 5a and 5b were around 18.98% and 45.16%, respectively. The best IE% value that was recorded for the derivative 3a has the potential to be effective anticorrosive coatings for industrial applications and act as mixture inhibitor because their ΔEcorr values are less than 85 mV. On the CS surface following treatment with compound 3a, the inhibitor mechanism for acidic medium (HCl) was investigated.

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Zenkevich, E., T. Blaudeck, M. Abdel-Mottaleb, F. Cichos, A. Shulga, and C. von Borczyskowski. "Photophysical properties of self-aggregated porphyrin: semiconductor nanoassemblies." International Journal of Photoenergy 2006 (2006): 1–7. http://dx.doi.org/10.1155/ijp/2006/90242.

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Colloidal semiconductor nanocrystals from CdSe show photoluminescence quenching via titration with porphyrin derivatives. This quenching is an indication of the formation of nanoassemblies via surface attachment of pyridyl linker groups. As a consequence of the complex formation, dynamic and/or static interactions between QD and porphyrins are induced. Quenching efficiencies depend critically on sample stability, temperature, solvent, and electronic properties of the porphyrins. In order to optimize photoinduced dynamic processes these parameters have to be under control.

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