Issue 12, 2023

Crystalline radicals derived from boron-dipyrromethene and its heavier analogues

Abstract

Boron-dipyrromethene (BODIPY) compounds have been the subject of intense scrutiny over the past few decades owing to their unique properties and various applications; however, structurally characterized BODIPY-centered radicals are still limited and isolable radicals derived from heavier analogues of BODIPY have never been described. Herein, we report the facile isolation and structural characterization of the first series of radicals [K(THF)2][TripDPMBF2] (4), [K(η6-toluene)][TripDPMAlI2] (5), and [TripDPMGaI(iPrNHC)] (6) derived from boron-dipyrromethene TripDPMBF2 (1) and its heavier analogues TripDPMAlI2 (2) and TripDPMGaI2 (3). Spectroscopy analysis, X-ray crystallography, and theoretical calculations reveal that one-electron reduction results in increasing delocalization over the dipyrromethene scaffold and the unpaired electrons in 46 are mainly delocalized over the dipyrromethene backbone with almost negligible spin density on the group 13 element centers.

Graphical abstract: Crystalline radicals derived from boron-dipyrromethene and its heavier analogues

Supplementary files

Article information

Article type
Research Article
Submitted
13 Feb 2023
Accepted
05 Mei 2023
First published
10 Mei 2023

Org. Chem. Front., 2023,10, 2949-2954

Crystalline radicals derived from boron-dipyrromethene and its heavier analogues

X. Wang, Z. Xie, Y. Dai, X. Liu, M. Bao, C. Liu, Q. Han, C. Liu and Y. Su, Org. Chem. Front., 2023, 10, 2949 DOI: 10.1039/D3QO00218G

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