Dipole-Mediated Rectification of Intramolecular Photoinduced Charge Separation and Charge Recombination
By Duoduo Bao , Srigokul Upadhyayula, Jillian M. Larsen , Bing Xia , Boriana Georgieva , Vicente Nuñez , Eli M. Espinoza , Joshua D. Hartman , Michelle Wurch , Andy Chang , Chung-Kuang Lin , Jason Larkin , Krystal Vasquez , Gregory J. O. Beran , and Valentine I. Vullev
Published in ACS Publications
J. Am. Chem. Soc
2014
Abstract
Controlling charge transfer at a molecular scale is critical for efficient light harvesting, energy conversion, and nanoelectronics. Dipole-polarization electrets, the electrostatic analogue of magnets, provide a means for “steering” electron transduction via the local electric fields generated by their permanent electric dipoles. Here, we describe the first demonstration of the utility of anthranilamides, moieties with ordered dipoles, for controlling intramolecular charge transfer. Donor–acceptor dyads, each containing a single anthranilamide moiety, distinctly rectify both the forward photoinduced electron transfer and the subsequent charge recombination. Changes in the observed charge-transfer kinetics as a function of media polarity were consistent with the anticipated effects of the anthranilamide molecular dipoles on the rectification. The regioselectivity of electron transfer and the molecular dynamics of the dyads further modulated the observed kinetics, particularly for charge recombination. These findings reveal the underlying complexity of dipole-induced effects on electron transfer and demonstrate unexplored paradigms for molecular rectifiers.
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