期刊
CHINESE CHEMICAL LETTERS
卷 30, 期 12, 页码 2271-2273出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2019.07.027
关键词
BOPYPY; Pyrazine; Fluorescent dye; Unsymmetric; pH
资金
- National Natural Science Foundation of China [21542004]
- Young and Middle-aged Scientific and Technological Innovation Talents of Shenyang Science and Technology Bureau [RC170140]
- Natural Science Foundation of Liaoning Province [20170540721]
- Basic research on the application of Industrial Development of Shenyang Science and Technology Bureau [18013027]
- Liaoning BaiQianWan Talents Program
- Distinguished Professor Project of Liaoning province [20183532]
- Chinese Scholarship Council [20183058]
Novel 5,6,5,6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes (BOPYPYs) were obtained by reaction of pyrrole-2-carboxaldehyde with 1-(pyrazin-2-yl)hydrazine in the presence of Et3N-BF3.Et2O for the first time. The absorption maxima of pyrazine-fused BOPYPY are obviously bathochromic shifts, in contrast to those of the reported BOPPY, indicating that the discrepant substitute groups between pyridine and pyrazine result in the remarkable wavelength difference. The new series of BOPYPYs possess high molar extinction coefficients, high fluorescence quantum yields, and larger Stokes shifts. A Knoevenagel reaction of BOPYPY with 4-dimethylaminobenzaldehyde smoothly produced the dye with the extension of pi-conjugation. Dimethylamino-containing BOPYPY as a pH-responsive fluorescent sensor could detect pH value. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
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