Synthesis, Reactivity, and Properties of a Class of π‑Extended BODIPY Derivatives

A new family of π-extended BODIPY derivatives were obtained through the condensation of aldehyde and pyrrole in aqueous solution in the presence of HCl. The new rigid π-framework extends beyond the dipyrromethene unit, which is significantly different from classical BODIPYs in the electronic configu...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-12, Vol.86 (23), p.17110-17118
Main Authors: Li, Wanwan, Gong, Qingbao, Guo, Xing, Wu, Qinghua, Chang, Fei, Wang, Hua, Zhang, Fan, Hao, Erhong, Jiao, Lijuan
Format: Article
Language:English
Subjects:
Boron Compounds
Fluorescent Dyes
Pyrroles
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Summary:A new family of π-extended BODIPY derivatives were obtained through the condensation of aldehyde and pyrrole in aqueous solution in the presence of HCl. The new rigid π-framework extends beyond the dipyrromethene unit, which is significantly different from classical BODIPYs in the electronic configuration. Both π-extended BODIPYs displayed intense absorption and moderate emission with maxima around 565 and 620 nm, respectively, and showed interesting reactivity toward various nucleophiles. Moreover, these π-extended BODIPYs were developed as fluorescent probes for rapid and selective detection of GSH and were successfully applied for live-cell imaging.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02216