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

被引：16

作者：

Jiang, Xindong ^{[1
,3
]}

Yue, Shuai ^{[1
]}

Chen, Kepeng ^{[2
]}

Shao, Zhumei ^{[1
]}

Li, Chen ^{[1
]}

Su, Yajun ^{[1
]}

Zhao, Jianzhang ^{[2
]}

机构：

[1] Shenyang Univ Chem Technol, Coll Appl Chem, Shenyang 110142, Peoples R China

[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

[3] Hiroshima Univ, Grad Sch Sci, Dept Chem, Higashihiroshima 7398526, Japan

来源：

CHINESE CHEMICAL LETTERS | 2019年 / 30卷 / 12期

基金：

中国国家自然科学基金;

关键词：

BOPYPY; Pyrazine; Fluorescent dye; Unsymmetric; pH; HIGHLY FLUORESCENT; BODIPY DYES; BORON; DIPYRROMETHENE; PROBE; NIR;

D O I：

10.1016/j.cclet.2019.07.027

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2271 / 2273

页数：3

共 11 条

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