Heteroacenes Bearing the Pyrimidine Scaffold: Synthesis, Photophysical and Electrochemical Properties / Verbitskiy Egor V.,Cheprakova Ekaterina M.,Makarova Nadezhda I.,Dorogan Igor V.,Metelitsa Anatoly V.,Minkin Vladimir I.,Slepukhin Pavel A.,Svalova Tatyana S.,Ivanova Alla V.,Kozitsina Alisa N.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2016. - V. , l. 7. - P. 1420-1428.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

A convenient synthetic route to novel 7-substituted benzo{[}f]thieno{[}3,2-h]quinazoline and 8-substituted benzo{[}g, h]-dithieno{[}2,3-e:3',2'-j]perimidine systems, bearing the fused pyrimidine ring, has been advanced. A commercially available 5-bromopyrimidine was used as the starting material to obtain various polycyclic systems through the sequence of nucleophilic aromatic substitution of hydrogen (the S-N(H) reaction), Suzuki cross-coupling and oxidative photocyclization. Evidence for the structure of benzo{[}g, h]dithieno{[}2,3-e:3',2'-j]perimidines has been obtained by X-ray crystallographic analysis. Molecular orbital calculations (DFT), as well as redox and optical measurements for all new compounds have been performed. The data show that the reported polycyclic systems have potential for use in organic electronic applications.

Author keywords:

Nitrogen heterocycles; Sulfur heterocycles; Polycycles; Cyclization; Nucleophilic substitution; UV/Vis spectroscopy NUCLEOPHILIC-SUBSTITUTION; ORGANIC ELECTRONICS; HYDROGEN; SEMICONDUCTORS; CHEMISTRY; DENSITY

DOI:

10.1002/ejoc.201501450

Web of Science ID:

ISI:000372848000026

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	NUCLEOPHILIC-SUBSTITUTION; ORGANIC ELECTRONICS; HYDROGEN; SEMICONDUCTORS; CHEMISTRY; DENSITY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Verbitsky@ios.uran.ru
ResearcherID-Numbers	Metelitsa, Anatoly/J-4314-2012 Kozitsina, Alisa/S-6317-2017 Makarova, Nadezhda/B-1960-2017
ORCID-Numbers	Metelitsa, Anatoly/0000-0003-3645-5528 Makarova, Nadezhda/0000-0002-7196-9842 Dorogan, Igor/0000-0002-9084-4607 Minkin, Vladimir/0000-0001-6096-503X
Funding-Acknowledgement	Government of the Russian Federation {[}02.A03.21.0006]; Ural Branch of the Russian Academy of Sciences {[}15-21-3-6, 15-21-3-9]; Russian Foundation for Basic Research {[}14-03-01017-A, 14-03-00479-A, 14-03-31040-mol\_a]; Ministry of Education and Science of Russian Federation {[}1895]
Funding-Text	This work was supported by Government of the Russian Federation (contract number 02.A03.21.0006, Act 211), the Ural Branch of the Russian Academy of Sciences (project numbers 15-21-3-6 and 15-21-3-9), the Russian Foundation for Basic Research (research project numbers 14-03-01017-A, 14-03-00479-A, and 14-03-31040-mol\_a). N. I. Makarova, I. V. D., A. V. M., and V. I. M. would like to acknowledge financial support for the absorption, fluorescence and quantum chemical studies from the Ministry of Education and Science of Russian Federation within the framework of the State Assignment for Research (project number 1895).
Number-of-Cited-References	35
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	20
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	DH5QX