Premium
Stepwise Reduction of 9,10‐Bis(dimesitylboryl)anthracene
Author(s) -
Zheng Yang,
Xiong Jiao,
Sun Yangyang,
Pan Xiaobo,
Wu Jincai
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505766
Subject(s) - anthracene , moiety , chemistry , electron paramagnetic resonance , cyclic voltammetry , aromaticity , crystallography , photochemistry , stereochemistry , molecule , organic chemistry , nuclear magnetic resonance , electrochemistry , physics , electrode
Stepwise reduction of 9,10‐bis(dimesitylboryl)anthracene afforded an radical anion and a dianion, accompanied by stepwise changes of the aromaticity of the anthracene moiety. The radical has a planar semiquinoidal structure, while the dianion has a puckered quinoidal structure. The alteration of the geometries of the 9,10‐bis(dimesitylboryl)anthracene upon reduction is rationalized by the nature of the bonding. These results have been confirmed by cyclic voltammetry, X‐ray crystallography, NMR, EPR, and UV‐vis‐NIR spectroscopy, as well as DFT calculations.