Starazo triple switches - synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes.

ABSTRACT

Multistate switches allow to drastically increase the information storage capacity and complexity of smart materials. In this context, unsymmetrical 1,3,5-tris(arylazo)benzenes - 'starazos' - which merge three photoswitches on one benzene ring, were successfully prepared. Two different synthetic strategies, one based on Baeyer-Mills reactions and the other based on Pd-catalyzed coupling reactions of arylhydrazides and aryl halides, followed by oxidation, were investigated. The Pd-catalyzed route efficiently led to the target compounds, unsymmetrical tris(arylazo)benzenes. These triple switches were preliminarily characterized in terms of their isomerization behavior using UV-vis and 1H NMR spectroscopy. The efficient synthesis of this new class of unsymmetrical tris(arylazo)benzenes opened new avenues to novel multistate switching materials.