Title

Isolation of a Chiral Anthracene Cation Radical: X-Ray Crystallography and Computational Interrogation of its Racemization

Document Type

Article

Language

eng

Publication Date

2-10-2017

Publisher

Royal Society of Chemistry

Source Publication

Chemical Communications

Source ISSN

1359-7345

Abstract

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).

Comments

Chemical Communications, Vol. 53 (February 10, 2017): 2748-2751. DOI.

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