Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives
Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives
复制标题
取代基对噻唑并[4,5-b]吡嗪衍生物荧光性质的影响
DOI：
10.1039/c4pp00298a
复制
发表时间：
2014
期刊：
影响因子：
--
通讯作者：
Takashi
中科院分区：
文献类型：
--
作者：
Nakagawa;Tatsuki; Yamaji;Minoru; Maki;Shojiro; Niwa;Haruki; Hirano;Takashi
基于光谱测量和密度泛函理论计算，研究了C2位含苯基的噻唑并[4，5-B]吡嗪（TPy）衍生物的荧光性质. TPys很容易从相应的氨基吡嗪制备，其具有与生物发光体Cypridina cuciferin相似的荧光核心。发现在TPy衍生物的2-苯基部分上引入给电子（甲氧基和二甲氨基）基团以及分别在C2和C6处的苯基和4-（二甲氨基）苯基增加了荧光产率和溶剂化变色特性的外观。讨论了取代基增加荧光产率的机制。这些发现为设计新的TPy荧光团提供了有用的信息。
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.