The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, China.
Chem Commun (Camb). 2020 Dec 25;56(99):15577-15580. doi: 10.1039/d0cc07259a. Epub 2020 Nov 27.
An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection.
本文首次报道了通过自由基过程，用亚硫酸钠将 BODIPY 染料直接磺酰化的高效、便捷的方法。该转化具有广泛的底物范围和高区域选择性，提供了一系列的α-磺酰化 BODIPY。有意义的是，磺酰基作为一个良好的离去基团，允许在 BODIPY 核心上轻松引入各种官能团。此外，带有 2,4-二硝基苯磺酰基（DBS）取代基的 BODIPY 通过光诱导电子转移（PET）途径显示出显著的荧光猝灭，被证明是一种用于选择性生物硫醇检测的新荧光探针。
