Solvatochromic and Single Crystal Studies of Two Neutral Triarylmethane Dyes with a Quinone Methide Structure

Molecules. 2015 Nov 19;20(11):20688-98. doi: 10.3390/molecules201119724.

Abstract

The crystal structure of two neutral triarylmethane dyes with a p-quinone methide core was determined by X-ray diffraction analysis. The spectroscopic characteristics of both compounds in 23 solvents with different polarities or hydrogen-bonding donor (HBD) abilities has been studied as a function of three solvatochromic parameters (ET(30), π* and α). Both compounds 1 and 2 showed a pronounced bathochromic shift of the main absorption band on increasing solvent polarity and HBD ability. The correlation is better for compound 2 than for compound 1. The stronger effect and better correlation was observed for compound 2 with the increment of the solvent HBD ability (α parameter).

Keywords: crystal structure; solvatochromic studies; triarylmethane dyes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coloring Agents / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Indolequinones / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis
  • Methane / chemistry*
  • Models, Chemical
  • Molecular Structure
  • X-Ray Diffraction

Substances

  • Coloring Agents
  • Indolequinones
  • quinone methide
  • Methane