Synthesis and Photophysical Studies of 2-(Thiophen-2-yl)-4-(morpholin-4-yl) quinazoline Derivatives

被引：22

作者：

Nosova, Emiliya V. ^{[1
,2
]}

Moshkina, Tatyana N. ^{[1
]}

Lipunova, Galina N. ^{[2
]}

Kopchuk, Dmitry S. ^{[1
,2
]}

Slepukhin, Pavel A. ^{[1
,2
]}

Baklanova, Inna V. ^{[3
]}

Charushin, Valery N. ^{[1
,2
]}

机构：

[1] Ural Fed Univ, Dept Organ & Biomol Chem, Mira St 19, Ekaterinburg 620002, Russia

[2] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ural Branch, S Kovalevskoy St 22,Akad Skaya St 20, Ekaterinburg 620137, Russia

[3] Russian Acad Sci, Inst Solid State Chem, Ural Branch, Pervomaiskaya St 91, Ekaterinburg 620990, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 16期

基金：

俄罗斯基础研究基金会;

关键词：

Photophysics; Fluorescence; Charge transfer; Cross-coupling; Coupling reactions; Nitrogen heterocycles; Sulfur heterocycles; ORGANIC-DYES; FLUORESCENCE; TERPYRIDINE; ZN(II); RU(II); SERIES; CORES;

D O I：

10.1002/ejoc.201600404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2876 / 2881

页数：6

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