Synthesis, Photophysical and Redox Properties of the D-π-A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

被引:33
作者
Verbitskiy, Egor V. [1 ,2 ]
Schepochkin, Aleksandr V. [1 ]
Makarova, Nadezhda I. [3 ]
Dorogan, Igor V. [3 ]
Metelitsa, Anatoly V. [3 ]
Minkin, Vladimir I. [3 ,4 ]
Kozyukhin, Sergey A. [5 ]
Emets, Victor V. [6 ]
Grindberg, Vitaly A. [6 ]
Chupakhin, Oleg N. [1 ,2 ]
Rusinov, Gennady L. [1 ,2 ]
Charushin, Valery N. [1 ,2 ]
机构
[1] Russian Acad Sci, Ural Branch, I Postovsky Inst Organ Synth, Ekaterinburg 620137, Russia
[2] Ural Fed Univ, Ekaterinburg 620002, Russia
[3] Southern Fed Univ, Inst Phys & Organ Chem, Rostov Na Donu 344090, Russia
[4] Russian Acad Sci, Southern Sci Ctr, Rostov Na Donu 344006, Russia
[5] RAS, NS Kurnakov Gen & Inorgan Chem Inst, Moscow 119991, Russia
[6] RAS, Frumkin Inst Phys Chem & Electrochem, Moscow 119071, Russia
基金
俄罗斯基础研究基金会;
关键词
Pyrimidine; Carbazole; Nucleophilic aromatic substitution of hydrogen; Solvatochromism; Dye-sensitized solar cells; SENSITIZED SOLAR-CELLS; NONLINEAR-OPTICAL PROPERTIES; INJECTING ANCHORING GROUP; FIELD-EFFECT TRANSISTORS; 2 PYRIDYL GROUPS; FLUORESCENT DYES; ELECTROCHEMICAL PROPERTIES; RING; CHROMOPHORES; OLIGOMERS;
D O I
10.1007/s10895-015-1565-6
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Novel donor-pi-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet-visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells.
引用
收藏
页码:763 / 775
页数:13
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