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Journal articles on the topic 'Phthalocyanines – Derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

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 persisten

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2

Awaji, Ayoub, Baybars Köksoy, Mahmut Durmuş, Ateyatallah Aljuhani, and Shaya Alraqa. "Novel Hexadeca-Substituted Metal Free and Zinc(II) Phthalocyanines; Design, Synthesis and Photophysicochemical Properties." Molecules 24, no. 1 (2018): 77. http://dx.doi.org/10.3390/molecules24010077.

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The syntheses of a novel 1,4,8,11,15,18,22,25-octahexyloxy-2,3,9,10,16,17,23,24-octa-(4-trifluoromethoxyphenyl) phthalocyanine (3a) and its zinc(II) phthalocyanine derivative (3b) have been described and characterized by elemental analysis,1H NMR, 13C NMR, 19F NMR, mass, UV-Vis and FT-IR. The newly prepared metal-free phthalocyanine and its zinc(II) counterpart are soluble in most organic solvents. The photophysical and photochemical properties such as aggregation, fluorescence, singlet oxygen generation and photodegradation under light irradiation of these phthalocyanines have been investigat

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3

Dixon, Dabney W., Anila F. Gill, and Brian R. Sook. "Characterization of sulfonated phthalocyanines by mass spectrometry and capillary electrophoresis." Journal of Porphyrins and Phthalocyanines 08, no. 11 (2004): 1300–1310. http://dx.doi.org/10.1142/s1088424604000672.

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We report the characterization of sulfonated phthalocyanines using capillary electrophoresis and mass spectrometry. Derivatives investigated included the copper, cobalt, zinc and metal-free sulfonated phthalocyanines. In general, sulfonated phthalocyanines were found as aggregates in capillary electrophoresis separations, even at low concentration. Separations were much better at pH 9.0 than at pH 2.5. The addition of β-cyclodextrin did not alter the electropherograms significantly. The electropherograms of commercially available copper phthalocyanine-3,4',4″,4‴-tetrasulfonic acid and 4,4',4″,

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4

Lam, Herman, Sebastian M. Marcuccio, Polina I. Svirskaya, et al. "Binuclear phthalocyanines with aromatic bridges." Canadian Journal of Chemistry 67, no. 6 (1989): 1087–97. http://dx.doi.org/10.1139/v89-164.

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Three different binuclear phthalocyanines were prepared and characterized. Two of the binuclear phthalocyanines are cofacially linked by rigid naphthalene and anthracene spacers, while the third consists of a direct linkage between two phthalocyanine rings. The dicobalt, dicopper, and dizinc derivatives were prepared by inserting the metal into the metal-free species. The synthesis and the physical and spectroscopic properties of the precursor bisphthalonitriles are also included. Keywords: phthalocyanines, cofacial, binuclear, bisphthalonitriles.

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5

Mori, Satoru, and Norio Shibata. "Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines." Beilstein Journal of Organic Chemistry 13 (October 27, 2017): 2273–96. http://dx.doi.org/10.3762/bjoc.13.224.

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Phthalocyanines and subphthalocyanines are attracting attention as functional dyes that are applicable to organic solar cells, photodynamic therapy, organic electronic devices, and other applications. However, phthalocyanines are generally difficult to handle due to their strong ability to aggregate, so this property must be controlled for further applications of phthalocyanines. On the other hand, trifluoroethoxy-substituted phthalocyanines are known to suppress aggregation due to repulsion of the trifluoroethoxy group. Furthermore, the electronic characteristics of phthalocyanines are signif

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6

Burnham, Paul M., Isabelle Chambrier, David L. Hughes, et al. "Synthesis, lead lability and ring deformation of three 1,4,8,11,15,18,22,25-octasubstituted phthalocyaninato lead derivatives." Journal of Porphyrins and Phthalocyanines 10, no. 10 (2006): 1202–11. http://dx.doi.org/10.1142/s1088424606000570.

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The syntheses and attempted syntheses of some non-peripherally (1,4,8,11,15,18,22,25) octasubstituted lead phthalocyanines from their corresponding metal-free derivatives are described. Some compounds exhibited lability of the lead ion during work-up to regenerate the starting material. The results of single crystal X-ray diffraction analyses of 1,4,8,11,15,18,22,25-octahexyl-, 1,4,8,11,15,18,22,25-octa-iso-pentyl- and 1,4,8,11,15,18,22,25-octahexylsulfanyl lead phthalocyanines are reported and cast some light on the greater stability of 1,4,8,11,15,18,22,25-octahexylsulfanyl lead phthalocyani

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7

Jin, Shan, Gongzhen Cheng, George Z. Chen, and Zhenping Ji. "Tuning the maximum absorption wavelengths of phthalocyanine derivatives." Journal of Porphyrins and Phthalocyanines 09, no. 01 (2005): 32–39. http://dx.doi.org/10.1142/s1088424605000071.

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A new series of low-symmetry octasubstituted metal-free phthalocyanines with the general formula H 2 N x P β4− x ( OBu )8 ( x = 0-4) were synthesized by mixed condensation of two different substituted precursors (4,5-dibutoxy- phthalonitrile and 1,4-dibutoxy-2,3-dicyanonaphthalene). Their electronic absorption spectra and MALDI-TOF-MS were investigated. The regiospecific, nonlinear and linear substituent effects of alkoxyl groups on the positions of the Q-bands of phthalocyanines with different substituent groups at different peripheral positions were systematically investigated. The results c

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8

Penon, Oriol, Filippo Marsico, Davide Santucci, Laura Rodríguez, David B. Amabilino, and Lluïsa Pérez-García. "Multiply biphenyl substituted zinc(II) porphyrin and phthalocyanine as components for molecular materials." Journal of Porphyrins and Phthalocyanines 16, no. 12 (2012): 1293–302. http://dx.doi.org/10.1142/s1088424612501453.

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The preparation and physico-chemical characteristics of zinc(II) porphyrin and phthalocyanine derivatives with biphenyl units are reported. These compounds have been prepared as components for molecular electronics systems and rotor-based molecular machines, where the biphenyl units can act as paddles because they are oriented quasi-perpendicularly to the plane of the aromatic macrocycles which would be coordianted through the transition metal ion by an axial ligand. The minimalist design along with the absence of solubilizing groups leads to a low solubility of the compounds in organic solven

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9

Qian, Yuxin, Bo Liu, Wubiao Duan, and Qingdao Zeng. "Assemblies of porphyrin and phthalocyanine derivatives studied by STM." Journal of Porphyrins and Phthalocyanines 22, no. 09n10 (2018): 717–25. http://dx.doi.org/10.1142/s1088424618500803.

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Porphyrins and phthalocyanines are currently a prevalent topic with great potential due to their abundant photonic/electronic properties. The study of porphyrin or phthalocyanine supramolecular architectures on solid surfaces is laying the foundation for the further development of molecular electronics or other structures in applications. Above all, the invention of scanning tunneling microscopy (STM) has opened a new path to explore these concepts on surfaces. Self-assemblies on solid surfaces can be probed with STM at submolecular resolutions to disclose the conformations and arrangements of

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10

Araújo, Ana R. L., Augusto C. Tomé, Carla I. M. Santos, et al. "Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines." Molecules 25, no. 7 (2020): 1745. http://dx.doi.org/10.3390/molecules25071745.

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The reaction between organic azides and alkyne derivatives via the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) is an efficient strategy to combine phthalocyanines and analogues with different materials. As examples of such materials, it can be considered the following ones: graphene oxide, carbon nanotubes, silica nanoparticles, gold nanoparticles, and quantum dots. This approach is also being relevant to conjugate phthalocyanines with carbohydrates and to obtain new sophisticated molecules; in such way, new systems with significant potential applications become available. This review h

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11

Göl, Emre Y., and Engin Karabudak. "Mini-Review: “Ball-Type Phthalocyanines”: Similarities and Differences from Mono Phthalocyanines." Mini-Reviews in Organic Chemistry 16, no. 5 (2019): 410–21. http://dx.doi.org/10.2174/1570193x15666181025110759.

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Ball-type phthalocyanines are recently synthesized binuclear derivatives of the widely known phthalocyanine molecule. In the ball-type Pc molecule, two cofacially arranged Pc rings have four bridged substituents on the peripheral positions of benzenes. Due to their cofacially arranged phthalocyanine rings and, strong intramolecular and intermolecular interactions, ball-type phthalocyanines have different properties than their parent molecule and these structures have many potential application areas. This review describes three different synthesis methods of ball-type phthalocyanines; synthesi

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12

Gülmez, Asuman Dakoğlu, Meltem Göksel, and Mahmut Durmuş. "Silicon(IV) phthalocyanine-biotin conjugates: Synthesis, photophysicochemical properties and in vitro biological activity for photodynamic therapy." Journal of Porphyrins and Phthalocyanines 21, no. 07n08 (2017): 547–54. http://dx.doi.org/10.1142/s1088424617500481.

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Silicon (IV) phthalocyanines bearing one or two biotin groups on the axially positions were synthesized, and these novel phthalocyanines were characterized by elemental analysis and standard spectroscopic techniques such as FT-IR, [Formula: see text]H NMR, UV-vis and MALDI-TOF. The synthesized compounds are the first examples of axially biotin substituted silicon (IV) phthalocyanines. These phthalocyanines were designed as targeting photosensitizers for the treatment of cancer by photodynamic therapy (PDT) technique. The phthalocyanine ring was selected for its photosensitizer ability and the

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13

Carchesio, Manuela, Lucia Tonucci, Nicola d'Alessandro, Antonino Morvillo, Piero Del Boccio, and Mario Bressan. "Visible photostability of some ruthenium and platinum phthalocyanines in water and in the presence of organic substrates." Journal of Porphyrins and Phthalocyanines 14, no. 06 (2010): 499–508. http://dx.doi.org/10.1142/s1088424610002306.

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Water-soluble, metal-tetrasubstituted phthalocyanines ( -SO3H , MPcS and -COOH , MPcC) of platinum and ruthenium were synthesized and their photostability to visible light irradiation was determined. For the ruthenium phthalocyanines, the characteristic visible Q band of the phthalocyanines was almost totally suppressed after five days of irradiation. The platinum derivatives were instead more resistant to photodegradation, and the Q band did not decrease by more than 25%. The addition of carbonyl compounds to the phthalocyanine solution in water (at concentrations at least 1400-fold those of

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14

Durmuş, Mahmut, Colette Lebrun, and Vefa Ahsen. "Synthesis and characterization of novel liquid and liquid crystalline phthalocyanines." Journal of Porphyrins and Phthalocyanines 08, no. 10 (2004): 1175–86. http://dx.doi.org/10.1142/s1088424604000519.

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Peripheral and non-peripheral tetra(13,17-dioxanonacosane-15-hydroxy) substituted metal free-, Ni (II) and Zn (II) phthalocyanines have been synthesized from the corresponding phthalonitrile derivatives in the presence of the anhydrous metal salt ( NiCl 2 and Zn ( OOCCH 3)2) or a strong organic base. The new compounds have been characterised by elemental analyses, IR, NMR, mass spectra and electronic spectroscopy. The mesogenic properties of these new materials were studied by differential scanning calorimetry (DSC), optical polarised microscopy and X-ray investigations. The effects of periphe

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15

Göksel, Meltem, Ibrahim F. Sengul, Hakan Kandemir, and Mahmut Durmuş. "Novel carbazole containing zinc phthalocyanine photosensitizers: Synthesis, characterization, photophysicochemical properties and in vitro study." Journal of Porphyrins and Phthalocyanines 20, no. 06 (2016): 708–18. http://dx.doi.org/10.1142/s1088424616500401.

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Tetra and octa substituted novel zinc(II) phthalocyanines (3a and 5a) bearing carbazole groups were synthesized by cyclotetramerization of respective phthalonitrile derivatives (3 and 5). The zinc(II) phthalocyanines (3a and 5a) were converted into the water-soluble quaternized derivatives (3b and 5b) by utilizing dimethylsulphate as quaternizing agent. The synthesized novel compounds were confirmed thruogh FT-IR, UV-vis and MALDI-TOF mass spectroscopic data and elemental analysis as well. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generatio

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16

Cammidge, Andrew N., and Hemant Gopee. "Synthesis and properties of macrodiscotic triphenylenophthalocyanines." Journal of Porphyrins and Phthalocyanines 13, no. 02 (2009): 235–46. http://dx.doi.org/10.1142/s1088424609000267.

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Phthalocyanines present a flat, disk-like molecular profile and suitably substituted derivatives show discotic liquid crystalline behavior. Extension of the molecular π-system through benzofusion perturbes the phthalocyanine's basic properties, most notably shifting the absorption to longer wavelength. This paper describes our synthesis of triphenylenophthalocyanines where the benzene rings of phthalocyanines are replaced by triphenylene units. The resulting materials are macrodiscotic in nature. They show red-shifted absorption spectra and columnar mesophase behavior over a wide temperature r

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17

Cong, Fangdi, Hongzhen Jiang, Xiguang Du, Shulin Zhang, and Wei Yang. "Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines." Synthesis 53, no. 15 (2021): 2656–64. http://dx.doi.org/10.1055/a-1499-8865.

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AbstractIt is important for the synthesis and research of phthalocyanine compounds for these compounds to be easily obtained at low temperature. We observed that metal-free phthalocyanine was sometimes found in a simple system used to synthesize phthalocyanine precursors at room temperature, and further studies showed that the key to the effective formation of phthalocyanines at low temperature lay in the presence of equal volumes of alcohol and amine, in addition to substrate phthalonitriles and solvents, in the reaction system. A synthetic mechanism was proposed and facile syntheses have bee

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18

Saydan, Nil, Mahmut Durmuş, Meltem G. Dizge, et al. "Water-soluble phthalocyanines mediated photodynamic effect on mesothelioma cells." Journal of Porphyrins and Phthalocyanines 13, no. 06 (2009): 681–90. http://dx.doi.org/10.1142/s1088424609000863.

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The new peripherally 2-mercaptopyridine tetrasubstituted zinc phthalocyanine (2) and its quaternized derivative (3) have been synthesized and characterized by elemental analysis, IR, 1 H NMR spectroscopy, electronic spectroscopy and mass spectra. The quaternized compound (3) shows excellent solubility in water, which makes it a potential photosensitizer for use in photodynamic therapy (PDT) of cancer. Fluorescence and singlet oxygen quantum yield measurements were conducted on 2-mercaptopyridine appended zinc phthalocyanines in dimethylsulphoxide (DMSO) for both the non-ionic (2) and quaterniz

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19

Pekbelgin Karaoğlu, Hande, та Ayfer Kalkan Burat. "α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties". Molecules 25, № 2 (2020): 363. http://dx.doi.org/10.3390/molecules25020363.

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Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubst

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20

GÜROL, I., and V. AHSEN. "Synthesis and aggregation behaviour of phthalocyanines substituted with flexible crown ether." Journal of Porphyrins and Phthalocyanines 04, no. 06 (2000): 621–26. http://dx.doi.org/10.1002/1099-1409(200009/10)4:6<621::aid-jpp231>3.0.co;2-6.

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The synthesis of metal-free and metallo derivatives ( Ni , Zn ) of tetrasubstituted phthalocyanines (Pcs) obtained from 4-[methyleneoxy(15-crown-5)]phthalonitrile is described. The new compounds have been characterized by elemental analyses, IR, 1 H and 13 C NMR , MS and UV-vis. The thermal stabilities of the compounds were determined by thermogravimetric analysis. The alkali metal ions bound to crown ether groups force dimerization of the phthalocyanine units in solution, as observed in the electronic spectra by the broadening of the Q band transition at 675 nm. The highest affinity for potas

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21

Gürol, İlke, Gülay Gümüş, Deniz Kutlu Tarakci, Ömer Güngör, Mahmut Durmuş, and Vefa Ahsen. "Photophysical and photochemical properties of fluoroether-substituted zinc(II) and titanium(IV) phthalocyanines." Journal of Porphyrins and Phthalocyanines 22, no. 01n03 (2018): 46–55. http://dx.doi.org/10.1142/s1088424618500074.

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The synthesis and characterization of novel zinc(II) (1a–4a) and oxo-titanium(IV) (1b–4b) phthalocyanine derivatives bearing 1H,1H-nona?uoro-3,6-dioxaheptan-1-ol groups are described for the first time. These phthalocyanines (1a–4a and 1b–4b) were characterized by elemental analysis and different spectroscopic techniques such as UV-vis, [Formula: see text]H NMR, FTIR and mass. Furthermore, the photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of these phthalocyanines were investigated in tetrahydrofuran (THF)

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22

Büyükekşi, Sebile Işık, Mahmut Durmuş, and Devrim Atilla. "Photophysical and photochemical properties of novel peripherally triethyleneoxysulfanyl substituted monomeric and Si–Si bonded dimeric silicon phthalocyanines." Journal of Porphyrins and Phthalocyanines 20, no. 12 (2016): 1426–37. http://dx.doi.org/10.1142/s1088424616501182.

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Monomeric and Si–Si bonded dimeric silicon(IV) phthalocyanines bearing 4[Formula: see text],7[Formula: see text],10[Formula: see text]-trioxaundecylsulfanyl groups were synthesized. These novel phthalocyanine derivatives were characterized by general analysis methods such as FT-IR, MALDI-TOF or HRMS, 1H NMR and UV-vis electronic absorption. Their aggregation behaviors were described in dimethyl sulfoxide (DMSO). In addition, the photophysical and photochemical properties of these phthalocyanines were also investigated in DMSO to determine potential of these phthalocyanines to acts as photosens

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23

Kuznetsova, Nina A., Dmitry A. Makarov, Olga A. Yuzhakova, Ludmila I. Solovieva, and Oleg L. Kaliya. "Study on the photostability of water-soluble Zn(II) and Al(III) phthalocyanines in aqueous solution." Journal of Porphyrins and Phthalocyanines 14, no. 11 (2010): 968–74. http://dx.doi.org/10.1142/s1088424610002835.

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The photodegradation of a series of water-soluble Zn(II) and Al(III) phthalocyanines has been studied in aerobic aqueous solutions. The photobleaching quantum yields of zinc phthalocyanine derivatives range from 2.2 × 10-4 for octacarboxy- to 1.5 × 10-5 for ZnPc , bearing 16 positively charged groups on periphery. Their aluminum counterparts are more photostable and photobleach with quantum yields in the narrow range (0.75 ÷ 2 × 10-6). The pH dependences of the photobleaching quantum yields for aluminum phthalocyanines show enhanced photodegradation for molecules with deprotonated axial H2O li

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24

Mızrak, Büşra, Meltem Ağar, Ahmet Altindal, and Şaziye Abdurrahmanoğlu. "Synthesis, characterization and metal ion sensing properties of novel pyridone derivatives phthalocyanines." Journal of Porphyrins and Phthalocyanines 20, no. 12 (2016): 1457–62. http://dx.doi.org/10.1142/s1088424616501200.

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The design of novel substituted phthalocyanines closely follows the requirement of their planned applications. In this study, synthesize of novel pyridone derivatives metal-free and symmetrical cobalt(II) phthalocyanines was carried out to improve brightness. For this purpose; starting with 4-nitrophthalonitrile and 4-hydroxy-6-methyl-3-nitro-2-pyridone, 4-(6-methyl-3-nitro-2-oxo-1,2-dihydropyridin-4-yloxy)phthalonitrile was prepared. Then 2(3),9(10),16(17),23(24)-tetrakis[6-methyl-3-nitro-2-oxo-1,2-dihydropyridin-4-yloxy] metal-free phthalocyaninato and 2(3),9(10), 16(17),23(24)-tetrakis[6-me

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25

Erdoğan, Buket S., Devrim Atilla, Ayşe G. Gürek, and Vefa Ahsen. "Liquid crystalline alkylthia-substituted novel phthalocyanines: synthesis and characterization." Journal of Porphyrins and Phthalocyanines 18, no. 01n02 (2014): 139–48. http://dx.doi.org/10.1142/s1088424613501149.

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Methylene-bridged tetra- and octa-alkylthia substituted metal free- and Ni ( II ) phthalocyanines were synthesized from the corresponding phthalonitrile derivatives in the presence of the anhydrous metal salt ( NiCl 2) or a strong organic base. The new compounds were fully characterized by elemental analyses, UV-vis, IR, NMR and mass spectra. The mesogenic properties of these materials were studied by differential scanning calorimetry, optical microscopy and X-ray diffraction investigations. X-ray diffraction patterns of the mesophase confirmed that the tetra- and the octa-substituted compound

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DE LA TORRE, GEMA, M. VICTORIA MARTÍNEZ-DÍAZ, and TOMÁS TORRES. "Synthesis of Fused Polynuclear Systems Based on Phthalocyanine and Triazolehemiporphyrazine Units." Journal of Porphyrins and Phthalocyanines 03, no. 07 (1999): 560–68. http://dx.doi.org/10.1002/(sici)1099-1409(199908/10)3:6/7<560::aid-jpp175>3.0.co;2-b.

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Unsymmetrically substituted binuclear phthalocyanine derivatives 8 and 9 have been synthesized by mixed condensation of nickel(II) dicyanophthalocyanine 6 with dioctyloxyphthalonitrile 7 in the presence of either nickel(II) or zinc(II) chloride. In addition, a heterotrinuclear phthalocyanine–triazolehemiporphyrazine–phthalocyanine complex 16 has been obtained using the methodology described earlier for the preparation of heterobinuclear phthalocyanine–triazolehemiporphyrazine systems (13a–13e). All these compounds exhibit in their UV-vis spectra broad and split Q bands that are shifted to the

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27

Nyokong, Tebello, and Hiroaki Isago. "The renaissance in optical spectroscopy of phthalocyanines and other tetraazaporphyrins." Journal of Porphyrins and Phthalocyanines 08, no. 09 (2004): 1083–90. http://dx.doi.org/10.1142/s1088424604000453.

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Spectral properties of metallophthalocyanines and other tetraazaporphyrins are governed mainly by the Q band which originates from the π-π* transitions within the ring. The position and intensity of the Q band is important in tailoring new phthalocyanine derivatives for particular applications. Aggregation, the nature of the central metal, π conjugation, symmetry of the molecules, and axial, peripheral or non-peripheral substitutions affect the spectra and hence the properties of the phthalocyanine molecule. This review gives a brief outline on how optical spectroscopy provides useful informat

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Fukuda, Takamitsu, and Nagao Kobayashi. "A colormap analysis method for visual presentation of the skeletal deformations of phthalocyanine derivatives." Journal of Porphyrins and Phthalocyanines 08, no. 11 (2004): 1251–57. http://dx.doi.org/10.1142/s108842460400060x.

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A two dimensional colormap analysis program customized for phthalocyanines and related macrocyclic compounds has been developed in order to effectively visualize the atomic displacements from the mean plane. Eleven known phthalocyanine structures, including super- and subphthalocyanines, have been analysed as examples using the program, and the distribution of the skeletal deformations within the molecules surveyed.

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29

Ayari, Sami, Mehmet F. Saglam, Elif Şenkuytu, et al. "3-Methylindole-substituted zinc phthalocyanines for photodynamic cancer therapy." Journal of Porphyrins and Phthalocyanines 23, no. 11n12 (2019): 1371–79. http://dx.doi.org/10.1142/s1088424619501426.

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Novel peripherally and non-peripherally 3-methylindole-substituted zinc phthalocyanine derivatives were synthesized as photosensitizers for photodynamic therapy in cancer treatment. The photophysical, photochemical and photobiological properties of targeted phthalocyanines were also investigated. For this purpose, the fluorescence and singlet oxygen quantum yields, and fluorescence lifetime values of the final compounds were determined in DMF solutions. The phototoxicity and cytotoxicity of the phthalocyanine complexes were tested against the invasive human breast cancer cell line (MDA-MB-231)

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30

Mızrak, Büşra, Efe Baturhan Orman, Şaziye Abdurrahmanoğlu, and Ali Rıza Özkaya. "Synthesis, characterization and electrochemical properties of novel pyridine phthalocyanine derivatives." Journal of Porphyrins and Phthalocyanines 22, no. 01n03 (2018): 243–49. http://dx.doi.org/10.1142/s1088424618500207.

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In this study, the novel Zn(II), metal-free and sandwich-type Lu(Pc)2 phthalocyanines containing tetra pyridine substituted at peripheral position were synthesized. All the new compounds have been characterized by FT-IR and UV-vis spectroscopy, [Formula: see text]H-NMR, MALDI-MS and elemental analysis. The electrochemical and spectroelectrochemical properties of all novel metallo- and metal free phthalocyanine compounds were also investigated by voltammetric and in situ spectroelectrochemical measurements on Pt in dimethylsulfoxide/tetrabutylammonium perchlorate.

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31

Bouvet, Marcel, Vicente Parra, Clémentine Locatelli, and Hui Xiong. "Electrical transduction in phthalocyanine-based gas sensors: from classical chemiresistors to new functional structures." Journal of Porphyrins and Phthalocyanines 13, no. 01 (2009): 84–91. http://dx.doi.org/10.1142/s108842460900019x.

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Phthalocyanines are organic-based materials which have attracted a lot of research in recent times. In the field of sensors, they present interesting and valuable potentialities as sensing elements for real gas sensor applications. In the present article, and taking some of our experiments as representative examples, we review the different ways of transduction applied to such applications. Some of the new tendencies and transducers for gas sensing based on phthalocyanine derivatives are also reported. Among them, electrical transduction (resistors, field-effect transistors, diodes, etc.) has

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32

Ayhan, M. Menaf, Mahmut Durmuş, and Ayşe G. Gürek. "Synthesis, photophysical and photochemical studies of novel liquid crystalline phthalocyanines." Journal of Porphyrins and Phthalocyanines 13, no. 06 (2009): 722–38. http://dx.doi.org/10.1142/s1088424609000917.

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Ni(II) and Zn(II) phthalocyanines carrying four or eight branched oligo(ethyleneoxy)-thia groups on peripheral positions have been synthesized from new phthalonitrile derivatives. The new compounds have been characterized by elemental analysis, IR, NMR, mass spectra and electronic spectroscopy. The aggregation behaviors of the phthalocyanine complexes were studied in different solvents and concentrations. General trends are described for photodegradation, singlet oxygen and fluorescence quantum yields, and fluorescence lifetimes of these compounds in dimethylsulfoxide (DMSO). The effects of th

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33

Semioshkin, Andrej, Olga Tsaryova, Olga Zhidkova, Vladimir Bregadze, and Dieter Wöhrle. "Reactions of oxonium derivatives of (B12H12)2- with phenoles, and synthesis and photochemical properties of a phthalocyanine containing four (B12H12)2- groups." Journal of Porphyrins and Phthalocyanines 10, no. 11 (2006): 1293–300. http://dx.doi.org/10.1142/s1088424606000661.

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The reactions of dodecahydro-closo-dodecaborate oxonium derivatives with various phenols resulted in phenoxy-undecahydro-closo-dodecaborates in high yields. Using this method, a phthalocyanine zinc(II) complex containing four ( B 12 H 12)2- species was prepared in high yield. The compound shows good photocatalytic activity. The combination of boron cages and phthalocyanines makes this compound useful for boron neutron capture therapy for cancer and photodynamic tumor therapy.

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34

Gürol, İlke, Gülay Gümüş, Emel Musluoğlu, Yadigar Arslan, and Vefa Ahsen. "Synthesis and characterization of O- and S-bridged perfluoroalkylated metal-free and zinc phthalocyanines." Journal of Porphyrins and Phthalocyanines 17, no. 06n07 (2013): 555–63. http://dx.doi.org/10.1142/s1088424613500491.

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The synthesis of tetra and octa perfluoroalkyl substituted zinc and metal free phthalocyanines ( ZnPc and H 2 Pc ) are reported. The compounds 1–5 have been prepared by nucleophilic substitution of 4-nitrophthalonitrile with 1H,1H,2H,2H-perfluorooctanethiol, 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol, 1H,1H-perfluorotetradecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol, respectively. The compounds 6–8 have been prepared by the reaction of 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol with 4,5-dichlororphthalonit

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35

Vashurin, Artur, Anna Filippova, Serafima Znoyko, et al. "A new water-soluble sulfonated cobalt(II) phthalocyanines: Synthesis, spectral, coordination and catalytic properties." Journal of Porphyrins and Phthalocyanines 19, no. 08 (2015): 983–96. http://dx.doi.org/10.1142/s1088424615500753.

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Novel complexes of cobalt(II) with sulfonated derivatives of phthalocyanines are synthesized. The influence of the sulfonated group's number in peripheral substituent on solubility of macrocycle and ability to form ordered structures in solution is showed. Transition from H-aggregates to monomeric phthalocyanine structures and sandwich-type dimers was found during formation of metallophthalocyanine complexes with 1,4-diazabicyclo[2.2.2]octane. The catalytic activity of metallophthalocyanines was studied on the model of Merox process.

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36

Attanasi, Orazio A., Giuseppe Ciccarella, Paolino Filippone, Giuseppe Mele, Jolanda Spadavecchia, and Giuseppe Vasapollo. "Novel phthalocyanines containing cardanol derivatives." Journal of Porphyrins and Phthalocyanines 07, no. 01 (2003): 52–57. http://dx.doi.org/10.1142/s1088424603000082.

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The synthesis and characterization of metal-free and metallo derivatives ( Cu , Zn , Ni , Pd ) of tetra-substituted phthalocyanines are described. The new compounds contain as a peripheral substituent 3-n-pentadecylphenol, a component of cardanol, which is a renewable organic source.

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Leznoff, Clifford C., Mougang Hu, Colin R. McArthur, Yongnian Qin, and Johan E. van Lier. "The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines." Canadian Journal of Chemistry 72, no. 9 (1994): 1990–98. http://dx.doi.org/10.1139/v94-254.

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2,9,16,23-Tetra-p-n-butylbenzyloxy-, 2,9,16,23-tetradiphenylmethoxy-, 2,9,16,23-tetramethoxymethoxy-, and 1,8,15,22-tetra-p-n-butylbenzyloxyphthalocyanines were synthesized from the appropriate phthalonitriles. Metal-free phthalocyanines were converted to their zinc derivatives. Cleavage from the appropriate precursor with trifluoroacetic acid produced 2,9,16,23-tetrahydroxyphthalocyanine and 1,8,15,22-tetrahydroxyphthalocyanine and their zinc derivatives. NMR spectroscopy revealed that all the 2,9,16,23-tetrasubstituted phthalocyanines are the usual mixtures of the 2,9,16,23, 2,9,16,24, 2,9,1

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38

Sorescu, Ana-Alexandra, Alexandrina Nuţă, Rodica-Mariana Ion, Ioana-Raluca Şuică-Bunghez, and Cristina Lavinia Nistor. "Hybrid Nanoaggregates from Plant-Based Noble Metallic Nanoparticles and Functionalized Macrocyclic Derivatives." Proceedings 41, no. 1 (2019): 71. http://dx.doi.org/10.3390/ecsoc-23-06653.

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Noble metallic nanoparticles, silver (AgNPs) and gold (AuNPs) mainly, exhibit good antimicrobial, antibacterial, and antifungal properties and, therefore, have a significant contribution to the constant growing field of nanomedicine. They can be synthesized using both conventional or unconventional methods and, in the last decades especially, the unconventional routes that use plants as raw vegetal materials are studied with proven results. On the other hand, macrocyclic derivatives such as phthalocyanines (Pcs) have photoactive properties and numerous applications. The conjugation between sil

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NAZEERUDDIN, MD K., R. HUMPHRY-BAKER, M. GRÄTZEL, et al. "Efficient Near-IR Sensitization of Nanocrystalline TiO2 Films by Zinc and Aluminum Phthalocyanines." Journal of Porphyrins and Phthalocyanines 03, no. 03 (1999): 230–37. http://dx.doi.org/10.1002/(sici)1099-1409(199903)3:3<230::aid-jpp127>3.0.co;2-l.

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Several zinc(II) and aluminum(III) phthalocyanines substituted by carboxylic acid and sulfonic acid groups were anchored to nanocrystalline TiO 2 films. By irradiation with visible light the photovoltaic behavior of the electrodes containing LiI / LiI 3/propylene carbonate electrolyte was measured. Most efficient results were found using zinc(II) 2,9,16,23-tetracarboxyphthalocyanine, with a current conversion efficiency at 700 nm approaching 45%. It is shown that electron injection into TiO 2 occurs from the excited singlet state of the phthalocyanine derivatives. High stability of the cell pe

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40

Kalashnikova, I. P., and V. E. Baulin. "Synthesis of Water-Soluble Phthalocyanines and Modification of their Peripheral Fragments as a Method of Directed Changes in Lipophilic-Hydrophilic Properties." Biomedical Chemistry: Research and Methods 1, no. 3 (2018): e00024. http://dx.doi.org/10.18097/bmcrm00024.

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This article brief by describes results of studies devoted to synthesis of water-soluble phthalocyanines derivatives, which are carried out by the Complexing Agents Chemistry group of IPAC RAS. Metal-free ligands and metallophthalocyanines, containing peripheral substituents with fragments of pyridine, oxybenzoic and hydroxyphenylphosphonic acids are potential photosensitizers for photodynamic therapy of cancer diseases. Methods for the modification of peripheral substituents have been developed that make it possible to synthesize phthalocyanine ligands and complexes soluble in organic solvent

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Heeney, Martin J., Shaya A. Al-Raqa, Aurélien Auger, et al. "Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overview." Journal of Porphyrins and Phthalocyanines 17, no. 08n09 (2013): 649–64. http://dx.doi.org/10.1142/s108842461330005x.

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The paper reviews a selection of synthetic pathways that provide access to 3,6-disubstituted phthalonitriles, precursors for the synthesis of 1,4,8,11,15,18,22,25-octasubstituted phthalocyanine derivatives. Early routes using Diels–Alder reactions for the synthesis of 3,6-dialkyl, 3,6-dialkoxymethyl, 3,6-dialkenyl and 3,6-diphenylphthalonitriles are appraised. However, the emphasis of the review focuses on the scope and applications of 2,3-dicyanohydroquinone as a starting material for obtaining 3,6-disubstituted phthalonitriles. The earliest example of the use of 2,3-dicyanohydroquinone conce

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42

Chambrier, Isabelle, Michael J. Cook, Denise A. Mayes, and Colin MacDonald. "NMR spectroscopic evidence for the self-association of some asymmetrically substituted phthalocyanines in solution." Journal of Porphyrins and Phthalocyanines 07, no. 06 (2003): 426–38. http://dx.doi.org/10.1142/s1088424603000550.

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1 H NMR data obtained for two series of asymmetrically octasubstituted metal-free and zinc phthalocyanines, bearing one or two hydroxyalkyl groups, indicate a degree of solution phase aggregation particular to the systems. The metal-free derivatives appear to stack cofacially through the interaction of their π systems and give rise to unusually well resolved, solvent, temperature and concentration dependent 1 H NMR spectra. Structural features for the aggregates, in which the phthalocyanine rings are cofacial but offset in a particular way, are proposed based on the NMR data. The zinc derivati

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Özkan Garip, Ebru, Mukaddes Özçeşmeci, Ramazan Katırcı, İbrahim Özçeşmeci, and Esin Hamuryudan. "Unsymmetrical phthalocyanines containing azo moiety; Synthesis and photophysical properties." Journal of Porphyrins and Phthalocyanines 23, no. 11n12 (2019): 1563–69. http://dx.doi.org/10.1142/s1088424619501724.

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Unsymmetrical metal-free phthalocyanine was synthesized through cyclotetramerization of 4-[2,6-dimethyl-4-(4-tert-butyl-phenylazo)phenoxy]phthalonitrile and 4-(hexylthio)phthalonitrile in the presence of lithium in [Formula: see text]-pentanol, then metal-free phthalocyanine was obtained by acidification with acetic acid. Finally, metalation was achieved by refluxing metal-free phthalocyanine in [Formula: see text]-pentanol in the presence of zinc (II) salt. The structure of synthesized phthalocyanine derivatives were characterized by using proton nuclear magnetic resonance, mass spectrometry,

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Tuhl, Ahmad, Wadzanai Chidawanayika, Hamada Mohamed Ibrahim, et al. "Tetra and octa(2,6-di-iso-propylphenoxy)-substituted phthalocyanines: a comparative study among their photophysicochemical properties." Journal of Porphyrins and Phthalocyanines 16, no. 01 (2012): 163–74. http://dx.doi.org/10.1142/s1088424612004495.

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This work reports on the synthesis of novel metal free, zinc, aluminum, gallium and indium tetra and octa (2,6-di-iso-propylphenoxy)-substituted phthalocyanine derivatives. UV-visible and 1H NMR analyses confirm that a non-planar conformation, adapted by the phenoxy substituents due to steric interaction in both derivative series, perfectly discourage cofacial aggregation. Fluorescence quantum yields vary as a function of the number of substituents on the ring periphery, while the fluorescence lifetimes display no distinct trend. Triplet quantum yields are significantly larger for the tetra 2,

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45

Atmaca, Göknur Yaşa, Hasan Yakan, Halil Kutuk, Mehmet Nebioğlu, Emre Güzel, and Ali Erdoğmuş. "Phthalocyanines with bromobenzenesulfanyl substituents at non-peripheral position: Preparation, photophysical and photochemical properties." Journal of Porphyrins and Phthalocyanines 23, no. 07n08 (2019): 821–27. http://dx.doi.org/10.1142/s1088424619500676.

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Electron-donating bromobenzenesulfanyl-group-substituted phthalonitrile derivative (1) and its novel non-peripherally tetra-substituted metal-free, indium and zinc phthalocyanine complexes (2–4) have been prepared for the first time. The chemical structures of this new phthalonitrile and its phthalocyanine derivatives were characterized by UV-vis, FT-IR, NMR, and MALDI-TOF mass spectrometry. The introduction of this electron-donating sulfanyl type of non-peripheral substituent accounts for a remarkable red shift of the phthalocyanine Q band to approximately 730 nm. Photophysical and photochemi

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Negrimovsky, Vladimir, Konstantin Volkov, Kyrill Suponitsky, and Evgeny Lukyanets. "C-Nucleophilic substitution in tetrachlorophthalonitrile — An approach to some new hexadecasubstituted phthalocyanines." Journal of Porphyrins and Phthalocyanines 17, no. 08n09 (2013): 799–806. http://dx.doi.org/10.1142/s1088424613500429.

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Reaction of tetrachlorophthalonitrile with some C -nucleophiles was studied. Only one chlorine atom was substituted regioselectively in the position 4 of benzene ring with diethyl malonate and malononitrile; no reaction occurred in case of bulkier diethyl ethylmalonate and ethylmalononitrile. In case of dimedone the domino substitution of two chlorine atoms, first with C -nucleophile followed by enolate O -nucleophile led to the mixture of two dibenzofuran derivatives. Remaining chlorine aroms n malonate and dibenzofuran derivatives were substituted with thiols, but in malononitrile derivative

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Göksel, Meltem, Mahmut Durmuş, and Devrim Atilla. "A comparative study on photophysical and photochemical properties of zinc phthalocyanines with different molecular symmetries." Journal of Porphyrins and Phthalocyanines 16, no. 07n08 (2012): 895–906. http://dx.doi.org/10.1142/s1088424612500964.

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The five possible non-peripherally substituted zinc(II) phthalocyanines with different molecular symmetries (Pc1–Pc5) were synthesized from statistical condensation of the phthalonitrile derivatives (A and B). 2-[2-(2-ethoxyethoxy)ethoxy]-1-[2-((2-ethoxyethoxy)-ethoxy)ethoxymethyl]ethyloxy and 2′-[(tert-butoxycarbonyl)amino]ethoxy groups were used as substituents. The structures of the new compounds were characterized using elemental analysis and spectroscopic data including IR, 1H and 13C NMR, electronic absorption and mass spectra. The photophysical and photochemical properties of these new

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Rodriguez-Mendez, Maria Luz, and José Antonio de Saja. "Nanostructured thin films based on phthalocyanines: electrochromic displays and sensors." Journal of Porphyrins and Phthalocyanines 13, no. 04n05 (2009): 606–15. http://dx.doi.org/10.1142/s1088424609000814.

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The group of the University of Valladolid is a multidisciplinary team formed by chemists, physicists and engineers. The activities of the group are focused to the study of the physicochemical properties of nanostructured Langmuir-Blodgett thin films based on phthalocyanines and their applications. Films of a variety of phthalocyanine molecules including several metallophthalocyanines, lanthanide double decker phthalocyanines and heteroleptic derivatives have been prepared. Their spectroelectrochemical properties have been described in detail and compared with those observed in disordered caste

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YILDIZ, S. ZEKİ, HALTİ KANTEKİN, and YAŞAR GÖK. "Synthesis and characterization of novel metal-free and metallophthalocyanines peripherally fused to four 24-membered tetraoxatetraaza macrocycles." Journal of Porphyrins and Phthalocyanines 05, no. 04 (2001): 367–75. http://dx.doi.org/10.1002/jpp.291.

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New metal-free 5 and metallophthalocyanines 6-11( M = Cu , Ni , Co , Pb , Zn ) fused in peripheral positions with four 24-membered tetraoxatetraaza macrocycles were prepared by cyclotetramerization of 24,25-dicyano-4,10,13,17-tetra(toluene-p-sulfonyl)-1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22-didicontinehydrobenzo[y][3,9,12,18]tetraaza[1,7,16,22]tetraoxatetradicontine in the presence of the corresponding metal salt or a strong organic base. While the N-tosylated derivatives of the phthalocyanines are soluble in common organic solvents, the detosylated derivative of copper phthal

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Wang, Dejun, Hui Li, Guangrui Wu, et al. "Photoelectrocatalytic degradation of partially hydrolyzed polyacrylamide using a novel particle electrode." RSC Advances 7, no. 87 (2017): 55496–503. http://dx.doi.org/10.1039/c7ra11658f.

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