Laboratory of Functional Molecular Solids, Ministry of Education; School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.
J Org Chem. 2020 Jul 2;85(13):8360-8370. doi: 10.1021/acs.joc.0c00620. Epub 2020 Jun 22.
A photoredox-mediated route to enamination of boron dipyrromethene (BODIPY) dyes with aliphatic amines is reported by activating both the β-C(sp)-H bond of amines and the α-C(sp)-H bond of BODIPYs under visible light illumination. Dehydrogenation of amines by excited-state BODIPYs and/or photoredox catalyst gave enamine intermediates, which were further trapped by BODIPYs to give a series of α-enamineBODIPYs. These resultant α-enamineBODIPYs showed red-shifted absorption and emission maxima with ratiometric pH-dependent fluorescence.
本文报道了一种光氧化还原介导的硼二吡咯亚甲基（BODIPY）染料与脂肪胺的胺化反应途径，该途径在可见光照射下同时激活了胺的β-C(sp)-H 键和 BODIPY 的α-C(sp)-H 键。受激态 BODIPY 和/或光氧化还原催化剂使胺脱氢，生成烯胺中间体，然后被 BODIPY 进一步捕获，得到一系列α-烯胺 BODIPY。这些生成的α-烯胺 BODIPY 表现出红移的吸收和发射最大值，以及与 pH 值相关的比率荧光。
