Synthesis and Photophysical Studies of 2-(Thiophen-2-yl)-4-(morpholin-4-yl) quinazoline Derivatives / Nosova Emiliya V.,Moshkina Tatyana N.,Lipunova Galina N.,Kopchuk Dmitry S.,Slepukhin Pavel A.,Baklanova Inna V.,Charushin Valery N. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2016. - V. , l. 16. - P. 2876-2881.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

The synthesis of a series of push-pull aryl and arylethynyl 2-(thiophen-2-yl) quinazoline derivatives is presented. The photophysical properties of the newly generated compounds are also described. Functionalization of the (2-thienyl) quinazoline fluorophore at the 5'-position with aryl and arylethynyl moieties was performed using bromination and subsequent palladium-catalyzed cross-coupling reactions. Optical studies revealed that 4-(diethylamino) phenyl and 4-(diphen-ylamino) phenyl derivatives emit green light upon irradiation, whereas their 4-(9H-carbazol-9-yl) phenyl, methoxyphenyl, thienyl and arylethynyl counterparts are characterized by blue light emission capabilities. The effect of protonation has also been studied, and the ability of some of these molecules to function as colorimetric and luminescent pH sensors has been demonstrated with significant color changes and luminescence switching upon the introduction of acid.

Author keywords:

Photophysics; Fluorescence; Charge transfer; Cross-coupling; Coupling reactions; Nitrogen heterocycles; Sulfur heterocycles SENSITIZED SOLAR-CELLS; LIGHT-EMITTING-DIODES; OPTICAL-PROPERTIES; ORGANIC-DYES; CHROMOPHORES; COMPLEXES; FLUORESCENCE; TERPYRIDINE; ZN(II); RU(II)

DOI:

10.1002/ejoc.201600404

Web of Science ID:

ISI:000379753900017

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	SENSITIZED SOLAR-CELLS; LIGHT-EMITTING-DIODES; OPTICAL-PROPERTIES; ORGANIC-DYES; CHROMOPHORES; COMPLEXES; FLUORESCENCE; TERPYRIDINE; ZN(II); RU(II)
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	emily74@rambler.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-00340]; Ural Division of Russian Academy of Sciences {[}15-21-3-7]; Act 211 Government of the Russian Federation {[}9.1.2.1.z1]
Funding-Text	This work was supported by the Russian Foundation for Basic Research (grant number 14-03-00340). Ural Division of Russian Academy of Sciences (project number 15-21-3-7) and Act 211 Government of the Russian Federation (contract number 9.1.2.1.z1).
Number-of-Cited-References	41
Usage-Count-Last-180-days	6
Usage-Count-Since-2013	20
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	DR2SJ