1,2,3-triazoles as conjugative pi-linkers in push-pull chromophores: importance of substituent positioning on intramolecular charge-transfer

Org Lett. 2008 Aug 7;10(15):3347-50. doi: 10.1021/ol801253z. Epub 2008 Jun 27.

Abstract

Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from lambda(max) = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Crystallography, X-Ray
  • Models, Molecular
  • Nitriles / chemistry*
  • Spectrophotometry, Ultraviolet
  • Triazoles / chemistry*
  • Vinyl Compounds / chemistry

Substances

  • Aniline Compounds
  • Nitriles
  • Triazoles
  • Vinyl Compounds