Li Wanwan, Gong Qingbao, Guo Xing, Wu Qinghua, Chang Fei, Wang Hua, Zhang Fan, Hao Erhong, Jiao Lijuan
The Key Laboratory of Functional Molecular Solids, Ministry of Education; School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.
J Org Chem. 2021 Dec 3;86(23):17110-17118. doi: 10.1021/acs.joc.1c02216. Epub 2021 Nov 8.
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.
通过醛和吡咯在盐酸存在下于水溶液中缩合，得到了一个新的π-扩展BODIPY衍生物家族。新的刚性π-骨架延伸至二吡咯亚甲基单元之外，这在电子构型上与经典BODIPY有显著不同。两种π-扩展BODIPY均显示出强烈的吸收和适度的发射，最大吸收峰和发射峰分别约在565和620 nm左右，并且对各种亲核试剂表现出有趣的反应活性。此外，这些π-扩展BODIPY被开发为用于快速、选择性检测谷胱甘肽（GSH）的荧光探针，并成功应用于活细胞成像。
