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

Authors

Mikhail V. Ivanov, Marquette University
Khushabu Thakur, Marquette University
Anshul Bhatnagar, Marquette University
Rajendra Rathore, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

2-10-2017

Publisher

Royal Society of Chemistry

Source Publication

Chemical Communications

Source ISSN

1359-7345

Original Item ID

DOI: 10.1039/c6cc10307c

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 (t_1/2) 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 t_1/2 10¹³–10¹⁷ years).

Comments

Accepted version. Chemical Communications, Vol. 53 (February 10, 2017): 2748-2751. DOI. © 2017 The Royal Society of Chemistry. Used with permission.

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Recommended Citation

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.
https://epublications.marquette.edu/chem_fac/915