Stepwise Reduction of 9,10-Bis(dimesitylboryl)anthracene.
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.
State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China).
Yang
Y
Zheng
State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China).
Jiao
J
Xiong
State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China).
Yangyang
Y
Sun
State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China). boxb@lzu.edu.cn.
Xiaobo
X
Pan
State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China). wujc@lzu.edu.cn.
Jincai
J
Wu
aromaticity; boron; density functional calculations; radicals; reduction