Royal Society of Chemistry
Original Item ID
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).
Ivanov, Mikhail V.; Thakur, Khushabu; Bhatnagar, Anshul; and Rathore, Rajendra, "Isolation of a Chiral Anthracene Cation Radical: X-Ray Crystallography and Computational Interrogation of its Racemization" (2017). Chemistry Faculty Research and Publications. 915.
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