Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter
Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter
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DOI：
10.1016/j.tetlet.2018.02.075
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发表时间：
2018-04-04
影响因子：
1.8
通讯作者：
Hirano, Takashi
中科院分区：
文献类型：
--
作者：
Fujikawa, Tomoya;Uehara, Takuya;Hirano, Takashi
制备了模仿萤火虫氧化荧光素结构的6-二甲氨基-2-苯基苯并噻唑(1a)及其苯基上带有吸电子取代基的衍生物，并研究了它们在各种溶剂中的荧光性能。 la 显示出具有良好荧光量子产率的溶剂化显色荧光（Phi(f) >0.8）。吸电子基团的引入导致发射最大值红移。特别是，具有2,2-二氰基乙烯基和(1,3-二氢-1,3-二氧代-2H-茚-2-亚基)甲基的衍生物在氯仿中显示出近红外荧光。此外，具有苯亚胺部分的衍生物表现出有效的固态荧光，这是由于分子排列抑制了分子间相互作用以猝灭晶体中的荧光状态。 (C) 2018 Elsevier Ltd. 保留所有权利。
6-Dimethylamino-2-phenylbenzothiazole (1a) mimicking the firefly oxyluciferin structure and the derivatives with an electron-withdrawing substituent on the phenyl group were prepared, and their fluorescence properties were investigated in various solvents. la showed solvatochromic fluorescence with good fluorescence quantum yields (Phi(f) >0.8). The introduction of an electron-withdrawing group led to a red-shift of the emission maximum. In particular, the derivatives with the 2,2-dicyanoethenyl and (1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)methyl groups showed near-infrared fluorescence in chloroform. In addition, the derivative with the phenylimine moiety showed efficient solid-state fluorescence, resulted from a molecular arrangement inhibiting intermolecular interactions for quenching the fluorescence state in crystals. (C) 2018 Elsevier Ltd. All rights reserved.