Thermodynamic and Kinetic Processes of Anthocyanins and Related Compounds and their Bio-Inspired Applications

Research output: Chapter in Book/Report/Conference proceedingConference contribution

12 Citations (Scopus)

Abstract

This chapter revisits the reversible pH-dependent chemistry of anthocyanins and related compounds, proposing a step-by-step procedure by which to calculate all the rate and equilibrium constants of their respective networks of chemical reactions. Self-aggregation dramatically changes the values of the rate and equilibrium constants of a network. The equilibrium constant (K-a) increases and the hydration (K-h) and global (K-a') constants decrease with increasing anthocyanin concentration. The hydration rate constant (k(h)) decreases as the dehydration rate constant (k(-h)) increases. Evidence for the formation of flavylium cation dimers aggregating according to a left-handed helix has been obtained from circular dichroism, while indirect evidence for a stronger aggregation in quinoidal base than in flavylium cation has been found. The chapter discusses the photochromism of synthetic flavylium compounds lacking or possessing a high cis-trans isomerization barrier; in the latter case, the system illustrates the concept of an optical memory capable of write-lock-read-unlock-erase. Extended conjugation in flavylium-derived compounds such as styryl-1-benzopyrylium and naphtoflavylium permits access to photochromic systems that present new switching colors. Dye-sensitized solar cells based on anthocyanins and synthetic flavylium analogs show the potential of flavylium compounds in practical devices. Two final sections explain in detail the steps required to construct the energy-level diagram of the network and the mole-fraction distribution of the respective species in solution.

Original languageEnglish
Title of host publicationRecent Advances in Polyphenol Research
EditorsA Romani, Lattanzio, S Quideau
PublisherWILEY-BLACKWELL
Pages341-370
Number of pages30
Volume4
ISBN (Electronic)978-111832963-4
ISBN (Print)978-111832967-2
DOIs
Publication statusPublished - 12 Aug 2014
Event26th International Conference on Polyphenols - Florence, Italy
Duration: 22 Jul 201226 Jul 2012

Publication series

NameRecent Advances in Polyphenol Research
PublisherWILEY-BLACKWELL
Volume4

Conference

Conference26th International Conference on Polyphenols
CountryItaly
CityFlorence
Period22/07/1226/07/12

Keywords

  • anthocyanins
  • flavylium
  • self-aggregation
  • photochromism
  • memories solar cells
  • SELF-ASSOCIATION
  • FLAVYLIUM COMPOUNDS
  • CIRCULAR-DICHROISM
  • FLASH-PHOTOLYSIS
  • AQUEOUS-SOLUTION
  • PROTON-TRANSFER
  • MALVIN
  • PHOTOCHROMISM
  • CHEMISTRY
  • HYDRATION

Cite this

Pina, F. (2014). Thermodynamic and Kinetic Processes of Anthocyanins and Related Compounds and their Bio-Inspired Applications. In A. Romani, Lattanzio, & S. Quideau (Eds.), Recent Advances in Polyphenol Research (Vol. 4, pp. 341-370). (Recent Advances in Polyphenol Research; Vol. 4). WILEY-BLACKWELL. https://doi.org/10.1002/9781118329634.ch11