Photochromism of flavylium systems. An overview of a versatile multistate system

Flavylium is the basic structure of anthocyanins, an important family of natural dyes responsible for the color in many flowers and fruits. While anthocyanins in vitro are involved in a pH dependent equilibrium between a flavylium cation (acidic species) and a hemiketal (as major basic species), some synthetic flavylium compounds present the trans-chalcone as the major basic species. In this case irradiation of the trans-chalcone leads to appearance of colored products, either a flavylium cation and/or a quinoidal base, via cis-chalcone and hemiketal. Taking profit from the complexity of the network it is possible to design photochromic systems, exhibiting a thermal back reaction, or models for optical memories, when the back reaction is prevented. The flavylium photochromism was also observed in ionic liquids, gels, micelles and reversed micelles opening up possible applications. In this work an overview of the photochromism of synthetic flavylium compounds is presented, from the first observations of the light effect to recent developments. (C) 2011 Elsevier Ltd. All rights reserved.