Exploring and improving the color stability of natural anthocyanins and synthetic derivatives and their application as pH/light-sensitive systems

Abstract

The color expression in Nature deserves the attention of scientists searching eco-friendly solutions to substitute pollutant synthetic dyes used in industrial processes. Being natural pigments, anthocyanins represent an affordable alternative; unfortunately, the colored structures in anthocyanins are only stable in very acidic conditions, forming colorless products as the pH increases, precluding a more widespread utilization of these compounds as dyes. This has motivated significant research efforts focusing on the development of new strategies toward color stabilization in anthocyanins and their application in formulations with different pHs in the coloring industry. On the other hand, the colorless structures are light-sensitive being responsible for the photochromic properties in some anthocyanins and synthetic derivatives. The study of photochromic transformations between uncolored and colored forms is important in the development of photochromic devices in the materials industry. In this thesis, a deep physical-chemical analysis of some natural mechanisms for color stabilization such as self-association, aggregation, and co-pigmentation was performed in anthocyanins and synthetic derivatives, in order to understand how Nature rules the expression of color. Some other methods based on supramolecular assemblies as host-guest interactions and micelle inclusions were also studied for the stabilization of both, colored and uncolored species, searching for the stabilization of color and improvement and application of the photochromic properties. Some results in natural anthocyanins indicate that the inter and intramolecular interactions during their self-association and aggregation processes, as well as the number of acylated units, result crucial in the stabilization of color and their water solubility. The co-pigmentation effect of the caffeine over the color stabilization was evaluated in a systematic way, employing a developed new method to explain the higher affinity of the co-pigment for the chromophores. The inclusion of anthocyanins and their synthetic derivatives into host receptors as molecular clips, calix[n]arenes, and micellar environments proved a high stabilization of the color along the pH scale. On the other hand, the photochromic properties of some synthetic flavylium systems were explored; the quantum yield of photoisomerization between uncolored and colored species was increased by the complexation with cyclodextrin as a host. The pH and light-sensitive properties of anthocyanins derivatives were exploited in the construction of a molecular timer controlled by changes in the pH and a system able to control the dissociation of boronate esters by photoisomerization

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