학술논문

Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives.
Document Type
Article
Source
Photochemical & Photobiological Sciences. 2014, Vol. 13 Issue 12, p1765-1772. 8p.
Subject
*SUBSTITUENTS (Chemistry)
*PYRAZINE derivatives
*THIAZOLES
*FLUORESCENCE
*DENSITY functional theory
*SOLVATOCHROMISM
Language
ISSN
1474-905X
Abstract
Based on spectroscopic measurements and DFT calculations, fluorescence properties of thiazolo[4,5-b]pyrazine (TPy) derivatives with the phenyl group at the C2 position were studied. TPys were readily prepared from the corresponding amidopyrazines, which have a similar fluorescent core to a bioluminescence light emitter, Cypridina oxyluciferin. It was found that the introduction of electron-donating (methoxy and dimethylamino) groups onto the 2-phenyl moiety of the TPy derivatives, as well as the phenyl and 4-(dimethylamino)phenyl groups at C2 and C6, respectively, increases the fluorescence yield and appearance of solvatochromic character. The mechanism of increasing the fluorescence yield depending on the substituents is discussed. These findings provide useful information on designing new TPy fluorophores. [ABSTRACT FROM AUTHOR]