Contents
Academic literature on the topic 'Photosensitizing compounds – Synthesis'
Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles
Consult the lists of relevant articles, books, theses, conference reports, and other scholarly sources on the topic 'Photosensitizing compounds – Synthesis.'
Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.
You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.
Journal articles on the topic "Photosensitizing compounds – Synthesis"
1
Sakamoto, Keiichi, Shouta Watabiki, Satoru Yoshino, and Tomoe Komoriya. "Synthesis of alkylthio substituted pyridoporphyrazines and their photophysicochemical properties." Journal of Porphyrins and Phthalocyanines 21, no. 10 (October 2017): 658–64. http://dx.doi.org/10.1142/s1088424617500626.
Full textAbstract:
Phthalocyanine and their related compounds are utilized as various applications, such as photosensitizing agents for photodynamic therapy of cancer. In this study, zinc bis(thiodidecylbenzo)-bis(pyrido)porphyrazines, especially zinc bis(1,4-didecylthiobenzo)-bis(3,4-pyrido)porphyrazine and zinc bis(1,4-didecylthiobenzo)-bis(2,3-pyrido)porphyrazine were synthesized. Quaternation of the pyridine nitrogen in these provides an amphiphilic property. Photoexcited triplet lifetime of synthesized and quaternized zinc bis(1,4-didecylthiobenzo)-bis(3,4-pyrido)porphyrazine and zinc bis(1,4-didecylthiobenzo)-bis(2,3-pyrido)porphyrazine were reported using laser-flash photolysis and singlet oxygen quantum yields by the 1,3-diphenylisobenzofurne method.
2
Arad, Ofir, Noemí Rubio, David Sánchez-García, José I. Borrell, and Santi Nonell. "Asymmetric porphycenes: synthesis and photophysical properties of 9-substituted 2,7,12,17-tetraphenylporphycenes." Journal of Porphyrins and Phthalocyanines 13, no. 03 (March 2009): 376–81. http://dx.doi.org/10.1142/s1088424609000462.
Full textAbstract:
The effects of 9-substitution on the photophysical properties of tetraphenylporphycenes (TPPo) have been examined using an electron acceptor, an electron donor, and an electroneutral substituent as model compounds. Introduction of the acetoxy group enhances the fluorescence ability of the compound, with only a small reduction in the singlet oxygen quantum yield. The optical and photophysical properties of a nitro-porphycene are reported for the first time. The compound is emerald green, contrasting with the typical blue color of porphycenes. While this compound is much less fluorescent than unsubstituted TPPo, its singlet oxygen quantum yield is only slightly lower, almost identical to that of the 9-acetoxy compound (9-AcOTPPo). Finally, the electron-donor amino group is found to induce the greatest changes in the porphycene photophysics, decreasing strongly its fluorescence and singlet oxygen quantum yields. With the exception of such electron donors, introduction of substituents at the 9 (meso) position of tetraphenylporphycenes is not detrimental to their photophysics and photosensitizing ability and thus can be exploited for targeted photodynamic therapy purposes.
3
Jamalis, Joazaizulfazli, Faten Syahira Mohamed Yusof, Subhash Chander, Roswanira Abd Wahab, Deepak P. Bhagwat, Murugesan Sankaranarayanan, Faisal Almalki, and Taibi Ben Hadda. "Psoralen Derivatives: Recent Advances of Synthetic Strategy and Pharmacological Properties." Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry 19, no. 3 (September 3, 2020): 222–39. http://dx.doi.org/10.2174/1871523018666190625170802.
Full textAbstract:
Psoralen or furocoumarin is a linear three ring heterocyclic compound. Psoralens are planar, tricyclic compounds, consisting of a furan ring fused to a coumarin moiety. Psoralen has been known for a wide spectrum of biological activities, spanning from cytotoxic, photosensitizing, insecticidal, antibacterial to antifungal effect. Thus, several structural changes were introduced to explore the role of specific positions with respect to the biological activity. Convenient approaches utilized for the synthesis of psoralen skeleton can be categorized into two parts: (i) the preparation of the tricyclic ring system from resorcinol, (ii) the exocyclic modification of the intact ring system. Furthermore, although psoralens have been used in diverse ways, we mainly focus in this work on their clinical utility for the treatment of psioraisis, vitiligo and skin-related disorder.
4
Silva, Eduarda M. P., Catarina I. V. Ramos, Patrícia M. R. Pereira, Francesca Giuntini, Maria A. F. Faustino, João P. C. Tomé, Augusto C. Tomé, et al. "Cationic β-vinyl substitutedmeso-tetraphenylporphyrins: synthesis and non-covalent interactions with a short poly(dGdC) duplex." Journal of Porphyrins and Phthalocyanines 16, no. 01 (January 2012): 101–13. http://dx.doi.org/10.1142/s1088424611004373.
Full textAbstract:
Several cationic beta-vinyl-pyridinium and beta-vinyl-quinolinium-meso-tetraphenylporphyrin derivatives were synthesized starting from 2-formyl-meso-tetraphenylporphyrin, and the corresponding Zn(II) complex, and different N-alkyl derivatives of 2- and 4-methylpyridine and 2- and 4-methylquinoline. The new compounds were obtained in a one-step process via base catalyzed aldol-type condensation reactions. Electrospray ionization mass spectrometry (ESI-MS) and ultraviolet-visible (UV-vis) spectroscopy were used to investigate the binding mode of the synthesized cationic beta-vinyl-pyridinium and beta-vinyl-quinolinium-meso-tetraphenylporphyrin derivatives with a short GC duplex oligonucleotide. Analysis of the obtained mass spectrometry results indicates the probable occurrence of outside binding. UV-vis spectroscopy data also points to non-intercalation. The potential photosensitizing capacity of these compounds was also ascertained from preliminary photophysical studies.
5
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 (June 2016): 708–18. http://dx.doi.org/10.1142/s1088424616500401.
Full textAbstract:
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 generation) properties of new phthalocyanines were determined in dimethylsulfoxide (DMSO). The photophysical and photochemical results were compared according to the number of the carbazole groups on the phthalocyanine core. Additionaly, in vitro photocytotoxicity of the targeted compounds were examined against to hepato cellular carcinoma (HuH-7) cancer cell line for determination of their photosensitizing ability.
6
Duc, Dau Xuan. "Recent Achievement in the Synthesis of Benzo[b]furans." Current Organic Synthesis 17, no. 7 (October 28, 2020): 498–517. http://dx.doi.org/10.2174/1570179417666200625212639.
Full textAbstract:
Background: Benzo[b]furan derivatives are oxygen-containing heterocyclic compounds consisting of fused benzene and furan rings and are present in a large number of natural and non-natural compounds. This class of compounds has a wide spectrum of biological activities, such as antiarrhythmic, anticancer, inflammatory, antioxidant, antimicrobial, and antiviral. Furthermore, benzo[b]furan derivatives have also been applied in various areas, such as organic electroluminescence device materials and organic dyes, photosensitizing material, organic synthesis as building blocks or intermediates. : Because of a broad range of applicability, the synthesis of benzo[b]furan derivative has drawn great attention of chemists and many studies on the synthesis of this class of compounds have been reported recently. This review will give an overview of benzo[b]furan preparation based on studies dating back to the year 2012. Objective: In this review, recent development in the synthesis of benzo[b]furans are discussed. There has been increasingly new methodologies for the construction of benzo[b]furans skeleton to improve efficiency or develop environmentally friendly procedures. In some studies, reaction mechanisms were also outlined. Conclusion: Many methods for the synthesis of benzo[b]furans have been reported recently. Most of them involve cyclization or cycloisomerization processes. Unquestionably, more imaginative strategies for the construction of benzo[b]furan skeleton will be established in the near future. Application of known methods to natural products or drug synthesis, on industrial scale for the synthesis of economically or medicinally important benzo[ b]furans will probably be paid attention to.
7
Donzello, Maria Pia, Fabio Gigante, Fabiola Sciscione, Elisa Viola, and Karl M. Kadish. "Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 18. Physicochemical properties and photochemical behavior of new uncharged water soluble low-symmetry macrocycles [{Pd(OAc)2}3(PtCl2)LM] (M = MgII(H2O), ZNII, PdII)." Journal of Porphyrins and Phthalocyanines 21, no. 04-06 (April 2017): 334–44. http://dx.doi.org/10.1142/s1088424617500250.
Full textAbstract:
The synthesis and physicochemical characterization of a new class of low-symmetry water soluble heteropentanuclear porphyrazine complexes are described. The investigated compounds, represented as [{Pd(OAc)[Formula: see text]}[Formula: see text](PtCl[Formula: see text]LM] •xH[Formula: see text]O where L [Formula: see text] tetrakis-2,3-[5,6-di(2-pyridyl)pyrazino]porphyrazinato dianion, M [Formula: see text] Mg[Formula: see text](H[Formula: see text]O), Zn[Formula: see text] or Pd[Formula: see text] and [Formula: see text] 3–8, were prepared under mild experimental conditions from the previously described heterobimetallic compounds [(PtCl[Formula: see text]LM]. Peripheral binding of one PtCl[Formula: see text]and three Pd(OAc)[Formula: see text]units in the new series of compounds occurs at the vicinal pyridine N atoms of each dipyridinopyrazine fragment via a “py–py” coordination. The newly synthesized porphyrazines were characterized by IR measurements in the solid state and UV-visible absorption spectroscopy in the polar nonaqueous solvents pyridine, dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) as well as in water, the enhanced solubility in this medium being due to the presence of the external Pd(OAc)[Formula: see text] moieties. Data on the photosensitizing activity of the compounds for the generation of singlet oxygen, [Formula: see text]O[Formula: see text] were also obtained in DMF and should be of interest to researchers in the area of photodynamic therapy.
8
Donzello, Maria Pia, Daniela Vittori, Elisa Viola, Lihan Zeng, Yan Cui, Karl M. Kadish, Luisa Mannina, and Claudio Ercolani. "Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 16. A rare class of uncharged water soluble complexes: UV-vis spectral, redox, and photochemical properties." Journal of Porphyrins and Phthalocyanines 19, no. 08 (August 2015): 903–19. http://dx.doi.org/10.1142/s1088424615500777.
Full textAbstract:
The synthesis and physicochemical characterization of a new class of water soluble homo/heteropentanuclear porphyrazine complexes are described. The investigated compounds, prepared from the previously reported mononuclear species [ LM ]⋅x H 2 O (L = tetrakis-2,3-[5,6-di(2-pyridyl) pyrazino]porphyrazinato dianion; M = MgII ( H 2 O ), ZnII , CuII , CoII , PdII , PtII ; x = 3–8) in DMSO under mild experimental conditions, are represented as [{ Pd ( OAc )2}4 LM ]⋅x H 2 O (x = 11–22) and bear four Pd ( OAc )2 units, each externally coordinated at the vicinal pyridine N atoms of a single dipyridinopyrazine fragment of the porphyrazine macrocycle (py–py coordination). The newly synthesized compounds were examined by IR and magnetic susceptibility measurements in the solid state. Solution UV-visible spectral studies on all of the species were conducted in the low-donor organic solvents pyridine, dimethyl sulfoxide and dimethylformamide and in the water medium, whereas electrochemical measurements were performed in these media in the presence of tetrabutylammonium perchlorate (organic solvents) and KCl or NaOAc (water). Data on the photosensitizing activity for the generation of singlet oxygen, 1 O 2, of interest in photodynamic therapy, were also obtained in dimethylformammide solution on the compounds [{ Pd ( OAc )2}4 LM ]( M = MgII ( H 2 O ), ZnII , PdII , PtII ) and the measured ΦΔ values are presented and discussed. NMR spectral data on the complex [{ Pd ( OAc )2}4 LZn ] are also included and discussed.
9
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 (July 2017): 547–54. http://dx.doi.org/10.1142/s1088424617500481.
Full textAbstract:
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 biotin group was selected as a targeting agent for increasing accumulation of these photosensitizers in tumor cells. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of the target silicon(IV) phthalocyanines were investigated in DMSO. The photosensitizing efficiency of the studied phthalocyanines was tested against human cervical cancer (HeLa) cells at different photosensitizer concentrations. Both axially mono- and bis-biotin substituted silicon(IV) phthalocyanines present high photocytotoxicity against HeLa cancer cells with the cell survival degree ranging from 13% to 50%. The photosensitivity and the intensity of damage were found to be directly related to the concentration of the used photosensitizers. According to the obtained results, both silicon(IV) phthalocyanine derivatives could be promising as photosensitizers for treatment of cancer by PDT technique.
10
Thomas, D. C., D. L. Svoboda, J. M. Vos, and T. A. Kunkel. "Strand specificity of mutagenic bypass replication of DNA containing psoralen monoadducts in a human cell extract." Molecular and Cellular Biology 16, no. 5 (May 1996): 2537–44. http://dx.doi.org/10.1128/mcb.16.5.2537.
Full textAbstract:
Psoralens are mutagenic compounds of vegetable origin that are used as photosensitizing agents in the treatment of various skin diseases, blood cell cancer, and autoimmune disorders. To study the mechanism of mutagenicity of psoralens in humans, we examined the efficiency and fidelity of simian virus 40 origin-dependent replication in a human cell extract of M13mp2 DNA randomly treated with the psoralen derivative 4'-hydroxymethyl-4,5',8-trimethyl psoralen plus UVA irradiation. Replication of DNA treated with variable amounts of 4'-hydroxymethyl-4,5',8-trimethyl psoralen and a fixed UVA fluence was inhibited in a concentration-dependent manner. However, covalently closed monomer-length circular replication products were observed. Product analysis by renaturing agarose gel electrophoresis after cross-linking with 250- to 280-nm UV light indicated that approximately 1 of 9 psoralen monoadducts was bypassed during in vitro replication. Introduction of product DNA into Escherichia coli to score replication errors in the lacZalpha reporter gene demonstrated that replication of the damaged DNA was more mutagenic than was replication of undamaged DNA. Sequence analysis of lacZ mutants revealed that damage-dependent replication errors were predominantly T.A-->C.G transitions, transversions at C.G base pairs, and deletions of single A.T base pairs, the last occurring most frequently in homopolymeric runs. A comparison of error specificities with two substrates having the replication origin asymmetrically placed on opposite sides of the mutational target suggests that the lagging-strand replication apparatus is less accurate than the leading-strand replication apparatus for psoralen monoadduct-dependent deletion errors. A model is proposed based on the preferential loopout of the monoadducted base from the strand that templates retrograde discontinuous synthesis.
Dissertations / Theses on the topic "Photosensitizing compounds – Synthesis"
1
Wong, Hei-ling. "Synthesis and photosensitizing properties of sublimable rhenium diimine complexes." Click to view the E-thesis via HKUTO, 2007. http://sunzi.lib.hku.hk/hkuto/record/B37865894.
Full text
2
Wong, Hei-ling, and 黃喜玲. "Synthesis and photosensitizing properties of sublimable rhenium diimine complexes." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2007. http://hub.hku.hk/bib/B37865894.
Full text
3
Tse, Chui-wan, and 謝翠雲. "Rhenium containing hyperbranched polymers for photonic applications." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2007. http://hub.hku.hk/bib/B38574512.
Full text
4
Huang, Lanqi. "Synthesis and characterization of benzodithiophene- and quinoxalinedithienothiophene-based semiconducting materials for organic solar cells." HKBU Institutional Repository, 2019. https://repository.hkbu.edu.hk/etd_oa/608.
Full textAbstract:
Organic semiconducting materials have been attracted considerable attention as a promising technology for the next generation flexible electronic devices, such as solar cells and field-effect transistors because of their advantages of low-cost, structural versatility and flexibility. Many organic semiconducting materials have been developed in recent years. In this thesis, four pi-conjugated building blocks based on benzodithiophene and quinoxalinedithienothiophene were applied to develop novel photovoltaic materials, including donor-acceptor alternating copolymers as a donor material for polymer solar cells, photosensitizers for dye sensitized solar cells, small molecule hole transporting materials for perovskite solar cells and small molecule acceptors for organic solar cells. A comprehensive review of current development of organic photovoltaic materials was presented in Chapter 1. In Chapter 2, a series of D-A copolymers (PBB-n) based on 4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole and 4,5-bis((2-ethylhexyl)oxy)benzo[2,1-b:3,4-b'] dithiophene attached with different solubilizing side-chains were designed, synthesised and characterized. In general, PBB-n polymers showed good absorption in the region of visible light and UV region, indicating such polymers are a promising light harvester. Also, PBB-n exhibited suitable energy levels, suggesting that they could be applied as the donor materials in polymer solar cells. PBB-n also exhibited various extent of aggregation behaviour. Chapter 3 described syntheses and the fluorination effect of two series of fluoro-substituted PBB-n copolymers, namely PfBB-n and PffBB-n on optical, electrochemical, and optoelectronic properties. Among them, PfBB-n series was characterized with photovoltaic performance. The champion devices fabricated from PfBB-12 showed a PCE as high as 9.7%, with a Voc of 0.92 V, a Jsc of 16.60 mA/cm-2 and a FF of 63.49%. Cells fabricated from other PfBB-n copolymers also exhibited good PV performance with PCE ranging from 7.4 - 8.5%. For PffBB-n polymers, temperature-dependent aggregation behaviour was exploited by modulating the coating temperature during device fabrication. PSC devices based on PffBB-n exhibited good PV performance with PCE ranging from 7.4% to 9.9%. Among which, PffBB-14 provided the most promising PV performance with PCE of 9.9%, a Voc of 0.92 V, a Jsc of 16.8 mA/cm-2 and a FF of 64.36%. Electron deficient conjugated structure was seldom used as the π-bridge in metal-free photosensitizers. In Chapter 4, four novel organic photosensitizers, namely QC5-m and PC5-n were designed with an electron deficient π-bridge. Typical sandwich-structured DSSCs based on the newly developed photosensitizers exhibited promising photovoltaic performance with PCE ranging from 5.23 - 7.77 %, with a maximum Jsc as high as 15.63 mA cm-2. These results suggest that the use of electron deficient π-bridge provides alternative approach to construct efficient organic photosensitizers. Chapter 5 and Chapter 6 described the design, synthesis and investigation of novel hole-transporting materials and electron acceptor materials based on benzo[2,1-b:3,4-b']dithiophene-4,5-dione derived building blocks as potential organic photovoltaic materials for solar cell applications. Keywords: organic photovoltaic materials, photosensitizers, polymer solar cell, electron acceptor, hole-transporting materials.
5
Hua, Yong. "Design and synthesis of new organic dyes for highly efficient dye-sensitized solar cells (DSSCs)." HKBU Institutional Repository, 2014. https://repository.hkbu.edu.hk/etd_oa/71.
Full textAbstract:
Dye-sensitized solar cell (DSSC) has attracted increasing interest as a promising hybrid organic-inorganic solar cell. At the heart of the device is a photosensitizer, which is anchored onto a wide-bandgap semiconducting metal oxide. It harvests solar light and transfers the energy via electron transfer to a suitable material (e.g. TiO2) to produce electricityas opposed to chemical energy in plant. The topic of this thesis focuses on the design and synthesis of metal-free organic dyes for applications in DSSCs. Specific attention has been paid to the correlation between the molecular structures and physical properties, as well as their performances in DSSCs. Chapter 1 presents the major components and working principle of DSSC, following by a brief overview of the development of organic dyes and their application in DSSCs. In chapter 2, we have designed two types of new phenothiazine-based dyes to investigate the positioning effect a donor group on the cell performance. The structural features of a donor aryl group at the C(7) position of phenothiazine core extend the π-conjugation of the chromophore and efficiently suppress the dye aggregation on TiO2 film. As a result, Type 1 dyes have better light harvesting properties in contact with TiO2 films, and give much better photovoltaic performance than Type 2 dyes. Chapter 3 presents the synthesis and characterization of a series of simple phenothiazine-based dyes, in which, a linear electron-rich (4-hexyloxy)phenyl group at C(7) of the phenothiazine periphery as the donor, and an alkyl chain with different length at N(10). The dye molecules show a linear shape which is favorable for the formation of a compact dye layer on the TiO2 surface, while their butterfly conformations can sufficiently inhibit molecular aggregation. Moreover, the alkyl substituents with different chain length at N(10) could further optimize the performance through complete shielding the surface of TiO2 from the Iˉ/I3ˉ electrolyte. Under simulated AM 1.5G irradiation, the PT-C6 based DSSC produces a short-circuit photocurrent of 15.32 mAcm−2, an open-circuit photovoltage of 0.78 V, a fill factor of 0.69, corresponding to a power conversion efficiency (PCE) of 8.18%. Moreover, we designed a stepwise approach for co-adsorption of the organic dye PT-C6 with a porphyrin dye (ZnP) for DSSCs. Upon optimization, the device made of the PT-C6 + ZnP system yielded Jsc = 19.36 mA cm-2, Voc =0.735 V, FF = 0.71 and η = 10.10%. In chapter 4, we further developed five organic dyes appended with T, TT, E, ET, or EE (T and E denote thiophene and 3,4-ethylenedioxythiophene (EDOT), respectively) on the C(7) atom of phenothiazine core as electron donors. We have also analyzed the structure-performance corelations of dye molecules in the aspect of dye aggregation, electron injection, dye regeneration and interfacial charge recombination of electrons with electrolytes and/or oxidized dye molecules, through DFT calculation, impedance analysis and transient photovoltage studies. In chapter 5, we extended our studies by using phenothiazine as a building block to construct 3D bulky organic dyes. We systematically investigated the influence of 3D bulky substituents on dye aggregation and charge recombination, as well as photovoltaic performance of DSSCs. The molecular design strategy demonstrates that high Voc can be realized by employing 3D-phenothiazine dyes featuring a bulky substituent, such as, hexylcarbazole and dihexylfluorene units. Impressively, the co-adsorbent-free DSSCs based on dye TP3 exhibits a photovoltaic performance with efficiency up to 8.00 %. In order to realize a panchromatic absorption and further enhance the energy conversion efficiency of DSSCs, we also designed a stepwise approach for co-adsorption of the organic dye TP3 with a NIR dye YR6 for co-sensitized DSSCs. Upon optimization, the device made of the TP3 + YR6 system yielded Jsc = 19.18 mA cm-2, Voc =0.721 V, FF = 0.712 and η = 9.84 %. The power-conversion efficiency is the highest reported efficiency for a squaraine dye-based co-sensitized panchromatic DSSCs. From chapters 6 and 7, a series of new simple panchromatic dyes based on thiadiazolo[3,4-c]pyridine (PyT) have been designed for panchromatic DSSCs. These new organic dyes exhibit broad absorption spectrum in the range of 300~850 nm and high molar extinction coefficients. The electrochemical analyses demonstrate that the incorporation of the auxiliary electron-deficient thiadiazole[3,4-c]pyridine unit can fine-tune the HOMO and LUMO energy levels and red-shift the absorption spectra to NIR region. The overall conversion efficiencies of liquid-electrolyte DSSCs based on these sensitizers range from 0.46 to 6.30 %. We draw some conclusions in chapter 8 together with the outlooks in DSSCs
6
Lai, Lai Fan. "Synthesis and characterization of new functional molecules and application studies in dye-sensitized and organic solar cells." HKBU Institutional Repository, 2014. https://repository.hkbu.edu.hk/etd_oa/81.
Full textAbstract:
This thesis describes the synthesis and characterization of a series of photosensitizers, transition metal-containing polymers and small organic molecules for dye-sensitized solar cells and organic solar cells. To begin with, a brief overview on the background of dye-sensitized solar cells (DSSCs) and organic solar cells was presented in Chapter 1. In Chapter 2, a series of novel donor-acceptor-π-acceptor bithiazole-based and fluorenone-based organic dyes for dye-sensitized solar cells were successfully synthesized and fully characterized. We discovered that the performance of the photovoltaic devices depends significantly on the nature and strength of the electron-donating end group along the conjugated main. Some of the materials have been found to show higher power conversion efficiency of 4.71% (Voc = 565 mV, Jsc = 11.71 mA cm–2, FF = 0.71) under AM 1.5 irradiation (100 mW cm–2). In Chapter 3, ten novel donor-donor-π-acceptor organic dyes for dye-sensitized solar cells have been synthesized and applied for the fabrication of DSSCs, including six dibenzothiophene-based photosensitizers and carbazole-based photosensitizers. All the dyes have efficient charge injection from the excited sensitizer molecule to TiO2 conduction band and can provide ample driving force for efficient dye regeneration best overall light to electricity conversion efficiency of 5.28% (Voc = 0.70 V, Jsc = 11.06 mA cm–2, FF = 0.68) under AM 1.5 irradiation, which reached 73% with respect to that of an N719-based device fabricated under similar fabrication conditions. Besides, nine novel di-anchoring organic sensitizers employing two different electron-donating cores, which are the fluorene and carbazole units, and two symmetrical anchoring cyanoacrylic acid (acceptor) termini have been synthesized and studied for their applications in DSSCs in Chapter 4. In Chapter 5, four new platinum polyyne polymers were prepared via the Sonogashira-type dehydrohalogenation reaction between the ethynyl precursor and trans-Pt(PBu3)2Cl2. All of the polymers are air-stable and well characterized by different spectroscopic methods and photophysical measurements. Their photovoltaic behaviors were fully investigated. Their model compounds were also prepared and studied. In Chapter 6, a series of new organic small molecules were designed and synthesized comprising head-to-head coupled heylthiophene, dithienosilole and dithienogermole units. They exhibited broad absorption peaks with favorable spectral overlap with the solar spectrum. These seven small molecules have been applied to presented. Among these molecules, the highest PCE of 4.93% was achieved with a Voc = 0.79 V, Jsc = 1.22 mA cm-2 and FF = 0.51 under illumination of an AM 1.5 solar cell simulator. Finally, Chapters 7 and 8 present the concluding remarks and the experimental details of the work described in Chapters 2−6
7
"Photodynamic activities and metal sensing behavior of boron dipyrromethenes and a silicon (IV) phthalocyanine." Thesis, 2010. http://library.cuhk.edu.hk/record=b6075089.
Full textAbstract:
At the end of this thesis, the 1H and 13C {1H} NMR spectra of all the new compounds are listed in the Appendix.Chapter 1 presents an overview of BODIPYs, including their general synthesis, properties, reactivities, and applications. The use of these compounds as photosensitizers for photodynamic therapy and fluorescent sensors for metal ions is highlighted.
Chapter 2 reports the synthesis, spectroscopic characterization, photophysical propreties, and in vitro photodynamic activities of a series of symmetrical distyryl BODIPYs substituted with one to five hydrophilic oligoethylene glycol monomethyl ether chain(s). In general, these compounds are essentially non-aggregated in DMF, resulting in a strong fluorescence emission and relatively high efficiency in generating singlet oxygen. Being formulated with 0.05% Tween 80, these compounds act as efficient photosensitizers. The compound which contains five triethylene glycol monomethyl ether chains exhibits the highest photocytotoxicity with an IC50 value as low as 7 nM toward HT29 human colorectal carcinoma cells. The high photodynamic activity of this compound can be attributed to its high efficiency in generating singlet oxygen, low aggregation tendency, and high cellular uptake. In addition, this compound also has a strong and selective affinity to the endoplasmic reticulum of the cells, causing cell death mainly through apoptosis.
Chapter 3 reports a related study on a series of unsymmetrical distyryl BODIPYs. These compounds possess three triethylene glycol monomethyl ether chains and another substituent at the other styryl group. The effects of this substituent on the photophysical properties, aggregation behavior, cellular uptake, and subcellular localization have been explored. Furthermore, their in vitro photodynamic activities have also been evaluated and compared with those of symmetrical analogues reported in Chapter 2.
Chapter 4 describes a novel ratiometric near-infrared fluorescent dye based on distyryl BODIPY with a 4-dimethylaminophenylethynyl group at the 2- and 6-positions. This compound exhibits a remarkable blue-shift in its absorption and fluorescence emission positions upon protonation with trifluoroacetic acid in organic solvents or HC1 in water in the presence of 0.05% Tween 80. These changes can be made reversible upon addition of a base.
Chapter 5 describes two monostyryl BODIPYs which contain two or four water-soluble amide chains as the metal chelators. The photophysical properties of these compounds and their spectral response to various metal ions have been investigated. The results show that the compound with two amide chains can detect Zn2+ ion in MeCN. They bind in a 1:1 stoichiometry with a binding constant of 2.2 x 104 M-1 . The fluorescence emission increases remarkably in intensity and shifts substantially to the blue from 620 to 572 nm due to the inhibition of the intramolecular charge transfer. The compound which contains four amide chains can detect Cd2+ ion with a high selectivity in phosphate buffered saline.
Chapter 6 reports the synthesis and spectral properties of a silicon(IV) phthalocyanine with two axial bis(2-picolyl)amine moieties which act as the binding sites for metal ions. The effects of various metal ions on its absorption and fluorescence spectra have been examined. The results indicate that this compound shows a relatively high sensitivity to Zn 2+ ion. Moreover, the proposed binding mode and the sensing mechanism are also discussed.
This thesis describes the synthesis and characterization of several series of functional boron dipyrromethenes (BODIPYs) and a silicon(IV) phthalocyanine. Their applications as efficient photosensitizers in photodynamic therapy and selective fluorescent sensors for metal ions are also reported herein.
He, Hui.
Adviser: Dennis Kee Pui Ng.
Source: Dissertation Abstracts International, Volume: 73-02, Section: B, page: .
Thesis (Ph.D.)--Chinese University of Hong Kong, 2010.
Includes bibliographical references.
Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [201-] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Abstract also in Chinese.
8
"Synthetic studies of functional zinc phthalocyanines and boron dipyrromethenes." Thesis, 2009. http://library.cuhk.edu.hk/record=b6074745.
Full textAbstract:
1H and 13C{1H} NMR spectra of all the new compounds and crystallographic data are given in the Appendix.Chapter 1 presents an overview of phthalocyanines including their general synthesis, properties, and applications. Special attention has been placed on the unsymmetrical analogues, and those which are efficient photosensitizers in photodynamic therapy. A brief account on BODIPYs as another versatile class of functional dyes is also given.
Chapter 2 describes the synthesis, spectroscopic characterization, photophysical properties, and in vitro photodynamic activities of three novel amphiphilic zinc(II) phthalocyanines substituted with one or two 3,4,5-tris(3,6,9-trioxadecoxy)benzoxy group(s). These compounds exhibit significantly higher photodynamic activities toward HepG2 and HT29 cell lines. The alpha-substituted analogue is particularly potent with IC50 values as low as 0.02 microM. The higher photodynamic activity of this compound can be attributed to its lower aggregation tendency in the culture media as shown by absorption spectroscopy and higher cellular uptake as suggested by the stronger intracellular fluorescence, resulting in a higher efficiency to generate reactive oxygen species inside the cells.
Chapter 4 focuses on a related series of 1,4-disubstituted zinc(II) phthalocyanines. These compounds possess two oligoethylene glycol methyl ether chains with various length at the 1,4-di-alpha-positions. The effects of the chain length on their aggregation, photophysical properties, cellular uptake, and in vitro photodynamic activities have been explored.
Chapter 5 presents the synthesis, characterization, and photophysical properties of another series of zinc(II) phthalocyanines conjugated with one, two or four isopropylidene protected glucofuranose unit(s) through a tetraethylene glycol linker. With these hydrophilic substituents, these macrocycles are highly soluble in common organic solvents and biological media. Their in vitro photodynamic activities toward HT29 and HepG2 cells have also been evaluated. Compared with the tetra-glucosylated phthalocyanines, which are almost nonphotocytotoxic, the mono- and di-glucosylated analogues exhibit a higher photodynamic activity. The di-alpha-substituted analogue is particularly potent with IC50 values as low as 0.03 microM.
Chapter 6 reports the synthesis, characterization, and photophysical properties of two novel conjugates of subphthalocyanine substituted axially with a BODIPY or distyryl-BODIPY moiety. Both systems absorb over a broad range in the visible region. They also exhibit a highly efficient photo-induced energy transfer process either from the excited BODIPY to the subphthalocyanine core or from the excited subphthalocyanine to the distyryl-BODIPY unit. The energy transfer quantum yields are close to unity for both of these conjugates.
Chapter 7 describes the preparation and photophysical properties of another two BODIPY and monostyryl-BODIPY conjugates which are linked to a silicon(IV) phthalocyanine core. These conjugates serve as excellent artificial photosynthetic models for the study of energy and electron transfer processes. Depending on the axial substituents, these conjugates exhibit predominantly a photo-induced energy or electron transfer process in toluene.
The related studies of a series of novel di-alpha-substituted zinc(II) phthalocyanines having two biocompatible triethylene glycol methyl ether chains or glycerol moieties are described in Chapter 3. Compared with the unsubstituted analogue, these compounds have a red-shifted Q band, and exhibit a relatively weaker fluorescence emission and higher efficiency to generate singlet oxygen. As a result, these compounds are promising candidates for photodynamic therapy. In vitro studies on HepG2 and HT29 cells have shown that they are highly photocytotoxic with IC50 values as low as 0.06 microM.
This thesis describes my synthetic studies on several series of functional zinc(II) phthalocyanines and boron dipyrromethenes (BODIPYs). Their applications as efficient photosensitizers in photodynamic therapy and light harvesting systems have also been explored.
Liu, Jianyong.
Adviser: Dennis Keepui Ng.
Source: Dissertation Abstracts International, Volume: 71-01, Section: B, page: 0326.
Thesis (Ph.D.)--Chinese University of Hong Kong, 2009.
Includes bibliographical references.
Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Electronic reproduction. Ann Arbor, MI : ProQuest Information and Learning Company, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Abstracts in English and Chinese.