Synthesis, Photophysical and Redox Properties of the D-pi-A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety / Verbitskiy Egor V.,Schepochkin Aleksandr V.,Makarova Nadezhda I.,Dorogan Igor V.,Metelitsa Anatoly V.,Minkin Vladimir I.,Kozyukhin Sergey A.,Emets Victor V.,Grindberg Vitaly A.,Chupakhin Oleg N.,Rusinov Gennady L.,Charushin Valery N. // JOURNAL OF FLUORESCENCE. - 2015. - V. 25, l. 3. - P. 763-775.

ISSN/EISSN:

1053-0509 / 1573-4994

Type:

Article

Abstract:

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.

Author keywords:

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

DOI:

10.1007/s10895-015-1565-6

Web of Science ID:

ISI:000354201800032

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	SPRINGER/PLENUM PUBLISHERS
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-4994
Keywords-Plus	SENSITIZED SOLAR-CELLS; NONLINEAR-OPTICAL PROPERTIES; INJECTING ANCHORING GROUP; FIELD-EFFECT TRANSISTORS; 2 PYRIDYL GROUPS; FLUORESCENT DYES; ELECTROCHEMICAL PROPERTIES; RING; CHROMOPHORES; OLIGOMERS
Research-Areas	Biochemistry \& Molecular Biology; Chemistry
Web-of-Science-Categories	Biochemical Research Methods; Chemistry, Analytical; Chemistry, Physical
Author-Email	Verbitsky@ios.uran.ru
ResearcherID-Numbers	Dorogan, Igor/F-9736-2015 Kozyukhin, Sergey/N-4063-2015 Metelitsa, Anatoly/J-4314-2012 Makarova, Nadezhda/B-1960-2017
ORCID-Numbers	Kozyukhin, Sergey/0000-0002-7405-551X Metelitsa, Anatoly/0000-0003-3645-5528 Makarova, Nadezhda/0000-0002-7196-9842 Minkin, Vladimir/0000-0001-6096-503X
Funding-Acknowledgement	Russian Foundation for Basic Research {[}13-03-96049-r\_ural\_a, 13-03-12434 ofi\_M2, 13-03-90606-Arm\_a, 14-03-01017-A, 14-03-00479-A, 14-03-31040-mol\_a, 13-03-12415]; Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation and Young Scientists) {[}MK-3939.2014.3]; Ministry of Education and Science of Russian Federation {[}1895]
Funding-Text	This work was supported by the Russian Foundation for Basic Research (research projects No. 13-03-96049-r\_ural\_a, 13-03-12434 ofi\_M2, 13-03-90606-Arm\_a, 14-03-01017-A, 14-03-00479-A and 14-03-31040-mol\_a, 13-03-12415), the Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation and Young Scientists, Grant MK-3939.2014.3). N.I. Makarova, I.V. Dorogan, A.V. Metelitsa and V.I. Minkin would like to acknowledge the financial support of absorption, fluorescence and quantum chemical studies from the Ministry of Education and Science of Russian Federation in the framework of the State Assignment for Research project No 1895.
Number-of-Cited-References	51
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	32
Journal-ISO	J. Fluoresc.
Doc-Delivery-Number	CH7FS