Metal-Containing Phthalocyanines Substituted with One Branched Bulky Moiety and Six Alkylthio Groups

Bayır, Zehra Altuntaş; Merey, Sebnur; Hamuryudan, Esin

doi:10.1007/s00706-003-0004-6

Cited by 23 publications

(8 citation statements)

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“…Additionally, both of them exhibit excellent thermal and chemical stability and tunable flexibility in their electronic and optical properties and molecular packing models in the solid state through synthetic modification by judiciously incorporating functional groups (such as alkyl chains or F/Cl atoms) at the outer positions of the cavity or in the molecule cavity with an appropriate metal atom (such as Cu, Zn etc.). 19,20 So the structural variety as well as their controllable electronic and optical properties have made them widely used as the active layer in organic optoelectronic devices, such as organic light-emitting diodes, organic fieldeffect transistors, and organic solar cells. It is worth noting that depending on the electron-donating/accepting characteristics of the incorporated substitutions, porphyrins can act as a donor or acceptor in the photovoltaic cells.…”

Section: Qing Mengmentioning

confidence: 99%

Organic photoresponse materials and devices

et al. 2012

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Organic photoresponse materials and devices are critically important to organic optoelectronics and energy crises. The activities of photoresponse in organic materials can be summarized in three effects, photoconductive, photovoltaic and optical memory effects. Correspondingly, devices based on the three effects can be divided into (i) photoconductive devices such as photodetectors, photoreceptors, photoswitches and phototransistors, (ii) photovoltaic devices such as organic solar cells, and (iii) optical data storage devices. It is expected that this systematic analysis of photoresponse materials and devices could be a guide for the better understanding of structure-property relationships of organic materials and provide key clues for the fabrication of high performance organic optoelectronic devices, the integration of them in circuits and the application of them in renewable green energy strategies (critical review, 452 references).

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Section: Qing Mengmentioning

confidence: 99%

Organic photoresponse materials and devices

et al. 2012

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“…The -NH 2 substituents can be further modified to form peripherally appended Schiff base metal chelates, 203,204,392 picalinomido chelates, 207,210,211 and peripheral pyrazine rings. 256 Selenodiazole fused porphyrinoids were originally reported by Ercolani and Stuzhin. [393][394][395] More recently, Hanack has reported the formation of novel AAAB structures by using a triazole ring fused to a Pc 396,397 or benzoporphyrazine 397 to form dehydro-compounds with a peripheral triple bond, which can be further modified via Diels-Alder reactions, 294 reactions with solvents, 397 and through ring-opening reactions to form azo-dye moieties.…”

Section: Selective Synthesismentioning

confidence: 99%

Low Symmetry Phthalocyanines and Their Analogues

2010

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“…Pcs 24-27 were also prepared in the presence of a large excess of lithium octanolate at 80-90 C, which increased the yield by up to 10% in comparison to the lithium pentanolate procedure but require a reaction time of 3 d instead of 2 h. Compounds 7, 10, 14, 16, 18, 21, 25 and 27 have been previously synthesized. 25,[40][41][42][43] Altered conditions were required for the preparation of Pc 17; 1 was substituted at À10 C to ensure the regioselective substitution at the 4 and 5 positions to give a mixture of monosubstituted phthalodinitrile 6 and di-substituted phthalodinitrile that was separated by column chromatography. The 1,2,4substitution pattern of 6 was confirmed by 19 F and 13 C NMR spectroscopy.…”

Section: Synthesismentioning

confidence: 99%

Halide effect in electron rich and deficient discotic phthalocyanines

et al. 2010

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A series of discotic octa-and tetra-alkylthio substituted phthalocyanines containing four Cl, Br, I atoms or twelve fluorine atoms have been prepared. All compounds display columnar mesomorphism as confirmed by polarized optical microscopy, thermal analysis, and variable temperature X-ray diffraction. Phthalocyanines containing halide atoms do not crystallize but form glassy or partially crystalline hexagonal columnar phases. Glass transition temperatures increase with increasing size of the halide atoms and with decreasing length of the alkyl chains. In contrast, all octa-and tetra-alkylthio substituted phthalocyanines crystallize and octa-substituted derivatives with aliphatic chain lengths of C 5-7 exhibit tilted (rectangular) columnar mesophases. Cyclic and differential pulse voltammetry, UV-Vis spectroscopy, and quantum chemical calculations at the DFT level have been employed to determine frontier orbital energies of all synthesized and some reference phthalocyanines. Octa-and tetra-alkylthio substituted phthalocyanines are typical p-type semiconductors and the introduction of four Cl, Br, or I atoms lowers frontier orbital energies by only up to 0.1 eV and the optical gap by up to 0.03 eV. A significant decrease in LUMO energy by 0.5 eV to about À4 eV is observed for the fluorinated phthalocyanine, which is a value right at the border of organic n-type semiconductors that may be stable in air.

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Metal-Containing Phthalocyanines Substituted with One Branched Bulky Moiety and Six Alkylthio Groups

Cited by 23 publications

References 0 publications

Organic photoresponse materials and devices

Organic photoresponse materials and devices

Low Symmetry Phthalocyanines and Their Analogues

Halide effect in electron rich and deficient discotic phthalocyanines

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