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Isolation of a chiral anthracene cation radical: X-ray crystallography and computational interrogation of its racemization.

Maxim V IvanovKhushabu ThakurAnshul BhatnagarRajendra Rathore
Published in: Chemical communications (Cambridge, England) (2018)
Chiral cation-radical salts hold significant promise as charge-transfer materials, chiroptical switches, and electron-transfer catalysts for enantioselective synthesis. Herein we demonstrate that the readily-available chiral 9,10-diphenyleanthracene derivative (i.e.SANT) forms a robust cation radical, whose structure was elucidated by X-ray crystallography and DFT calculations. While SANT was observed to racemize on a timescale (t1/2) of 1.1 hours, a computational conformational search and kinetic analysis of the racemization pathway led us to identify a simple methyl substituted SANT derivative, which does not racemize (racemization t1/2 1013-1017 years).
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