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Synthesis and Photophysical Studies of 2‐(Thiophen‐2‐yl)‐4‐(morpholin‐4‐yl)quinazoline Derivatives
Author(s) -
Nosova Emiliya V.,
Moshkina Tatya.,
Lipunova Gali.,
Kopchuk Dmitry S.,
Slepukhin Pavel A.,
Baklanova Inna V.,
Charushin Valery N.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600404
Subject(s) - chemistry , quinazoline , aryl , luminescence , halogenation , protonation , photochemistry , fluorophore , molecule , combinatorial chemistry , medicinal chemistry , organic chemistry , fluorescence , alkyl , ion , physics , optoelectronics , quantum mechanics
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‐(diphenylamino)phenyl derivatives emit green light upon irradiation, whereas their 4‐(9 H ‐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.