Citation: Jiang Xindong, Yue Shuai, Chen Kepeng, Shao Zhumei, Li Chen, Su Yajun, Zhao Jianzhang. Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs[J]. Chinese Chemical Letters, ;2019, 30(12): 2271-2273. doi: 10.1016/j.cclet.2019.07.027 shu

Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs

Jiang Xindong ^a,c,*, ,
Yue Shuai ^a ,
Chen Kepeng ^b ,
Shao Zhumei ^a ,
Li Chen ^a ,
Su Yajun ^a ,
Zhao Jianzhang ^b

a.
College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
c.
Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526, Japan

xdjiang@syuct.edu.cn

Received Date: 14 May 2019
Revised Date: 3 July 2019
Accepted Date: 11 July 2019
Available Online: 14 December 2019

Figures(5)

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 π-conjugation. Dimethylamino-containing BOPYPY as a pH-responsive fluorescent sensor could detect pH value.
- BOPYPY,
- Pyrazine,
- Fluorescent dye,
- Unsymmetric,
- pH
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Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes: BOPYPYs

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通讯作者: 陈斌, bchen63@163.com

Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs