Synthesis and structural diversification of CPL active, helically chiral ‘confused’ N,N,O,C‐BODIPYs

Helically chiral boron-chelated dipyrromethene (BODIPY) dyes are known to exhibit solution phase circularly polarized luminescence (CPL), but examples are limited to a few synthetically accessible molecular architectures. We report a B-N chelation, S N Ar, Suzuki cross-coupling, B-O chelation cascade reaction for the synthesis of understudied helically chiral, N , N , O , C -boron chelated, “confused” BODIPYs, from readily accessible 3,5-dibromo-BODIPY starting materials. Using this approach we have prepared a series of helically chiral “confused” BODIPYs with variation of the 3,5-subsitutents. Following resolution by chiral HPLC, absolute stereochemistry was assigned through comparison of the experimental and calculated ECD spectra, and solution phase chiroptical properties including CPL were determined (| g lum | from 2.1 to 3.7×10 -3 ; B CPL from 11.3 to 27.2).

Jaar van publicatie:2023

Trefwoorden:A1 Journal article

Toegankelijkheid:Open