Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter |
| |
Authors: | Tomoya Fujikawa Takuya Uehara Minoru Yamaji Takuya Kanetomo Takayuki Ishida Shojiro Maki Takashi Hirano |
| |
Affiliation: | 1. Department of Engineering Science, Graduate School of Informatics and Engineering, The University of Electro-Communications, Chofu, Tokyo 182-8585, Japan;2. Division of Molecular Science, Graduate School of Science and Engineering, Gunma University, Kiryu, Gunma 376-8515, Japan |
| |
Abstract: | 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. 1a showed solvatochromic fluorescence with good fluorescence quantum yields (Φf >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. |
| |
Keywords: | Firefly oxyluciferin Benzothiazole Fluorophore Solvatochromism Push-pull structure |
本文献已被 ScienceDirect 等数据库收录! |
|