Organic Letters 2009-06-04

X-ray structural characterization of charge delocalization onto the three equivalent benzenoid rings in hexamethoxytriptycene cation radical.

Vincent J Chebny, Tushar S Navale, Ruchi Shukla, Sergey V Lindeman, Rajendra Rathore

Index: Org. Lett. 11(11) , 2253-6, (2009)

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Abstract

Definitive X-ray crystallographic evidence is obtained for a single hole (or a polaron) to be uniformly distributed on the three equivalent 1,2-dimethoxybenzenoid (or veratrole) rings in the hexamethoxytriptycene cation radical. This conclusion is further supported by electrochemical analysis and by the observation of an intense near-IR transition in its electronic spectrum, as well as by comparison of the spectral and electrochemical characteristics with the model compounds containing one and two dimethoxybenzene rings.