Optimization of Azobenzene Molecular Switch in Organic Synthesis

Abstract

Photosensitive azobenzene molecules are potential molecular switches for a nanoscale optoelectronic device due to their properties that are based on fast, light-driven processes (1). An azobenzene derivative, 6,6'-difluoro-2,2'- dinitroazobenzene, is obtained in high yield (almost double) compared to other halogenated derivatives (2). Also, the fluorines on 6,6'-difluoro-2,2'- dinitroazobenzene can be easily displaced, thus allowing nucleophilic displacement to produce other derivatives. Optimizing the synthesis of 6,6'- difluoro-2,2'-dinitroazobenzene from 2-fluoro-6-nitroaniline by studying the effects of several reaction conditions, including heat, solvent, and concentration of oxidizing agent, will eventually and potentially lead to a route that produces the highest yield.

(1) Zhang, C.; Du, M.-H.; Cheng, H.-P.; Zhang, X.-G.; Roitberg, A. E.; Krause, J. L. Phys.Rev. Lett. 2004, 92, 158301-158304.

(2) Erdman, P. J. M.S. Thesis, University of Minnesota, Minneapolis, MN, 2006, 37-50.