Formation of a leuco spirolactone from 4-(2-carboxyphenyl)-7-diethylamino-4'-dimethylamino-1-benzopyrylium: design of a phase-change thermochromic system based on a flavylium dye

Chemistry. 2010 Jul 12;16(26):7760-6. doi: 10.1002/chem.200903482.

Abstract

A phase-change thermochromic system was designed through the reversible transformation of the 4-substituted flavylium dye 4-(2-carboxyphenyl)-7-diethylamino-4'-dimethylamino-1-benzopyrylium into its leuco form, in the presence of a developer (ethyldiisopropylamine) and a suitable solvent (e.g., acetonitrile, n-pentadecanonitrile). The leuco form of the flavylium-based dye is a spirolactone species whose ring opens at low temperature (below the solvent melting point) to form the blue flavylium cation. Decarboxylation of the lactone to give 4-phenyl-7-diethylamino-4'-dimethylamino-1-benzopyrylium was observed upon irradiation of the system with UV light, erasing the thermochromic effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Anthocyanins / chemistry
  • Flavonoids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Solvents / chemistry
  • Spironolactone / chemical synthesis*
  • Spironolactone / chemistry
  • Ultraviolet Rays

Substances

  • 4-(2-carboxyphenyl)-7-diethylamino-4'-dimethylamino-1-benzopyrylium
  • Acetonitriles
  • Anthocyanins
  • Flavonoids
  • Solvents
  • Spironolactone
  • acetonitrile