Photochromic properties of 3-methyl-substituted flavylium salts

Ana Roque, Carlos Lodeiro, Fernando Pina, Mauro Maestri, Roberto Ballardini, Vincenzo Balzani

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

The photochromic properties of some 3 -methyl -substituted synthetic flavylium compounds have been investigated. The main structural feature in these compounds is the existence of a steric effect, caused by the methyl substituent, that forces the phenyl ring to move out of coplanarity with the benzopyrylium moiety. The X-ray structure of 3-methylflavylium tetrafluoroborate shows a torsion angle of 40.4° between the benzopyrylium and the benzene ring. In 3-methyl-substituted synthetic flavylium compounds, the steric effect impedes the formation of trans-chalcone. In the case of the 4'-hydroxy-3- methylflavylium ion, for example, the trans-chalcone form could only be obtained (up to a maximum yield of 60%) by protonation of the trans-chalcone anion, obtained in turn by irradiation of anionic cis-chalcone in basic solution., The multistate/multifunctional properties of the 4'-hydroxy-3- methylflavylium compound are also discussed in detail. For the 4',7-dihydroxy-3- methylflavylium ion, a detailed investigation of the kinetic and thermodynamic properties of the various forms was performed by means of pH jumps and photochemical experiments.

Original languageEnglish
Pages (from-to)2699-2709
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
Publication statusPublished - Aug 2002

Keywords

  • Flavylium compounds
  • Information storage
  • Multifunctional systems
  • Multistate
  • Photochromism

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