Design and synthesis of a coumarin-based acidichromic colorant

Molecules. 2007 Jul 6;12(7):1316-24. doi: 10.3390/12071316.

Abstract

This paper describes the fine-tuning of the acidichromic properties of a coumarin-containing colorant 1 by incorporation of electron-donating and electron-withdrawing substituents on the coumarin moiety. Colorant 1 can undergo two distinct and reversible color changes under both strongly acidic and basic conditions, but not in the presence of gaseous ammonia. The results indicated that the bromo-substituted compound 5b changes from red to yellow when exposed to gaseous ammonia, both in solution and on polycarbonate film, suggesting that an electron-withdrawing group at the 7-position of the coumarin moiety made the enolic hydrogen on 5b more susceptible to deprotonation by a base than in the unsubstituted compound 1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Color
  • Coloring Agents / chemical synthesis*
  • Coloring Agents / chemistry
  • Coumarins / chemistry*
  • Hydrogen-Ion Concentration
  • Spectrophotometry, Ultraviolet
  • Titrimetry

Substances

  • Coloring Agents
  • Coumarins
  • coumarin