Synthesis and photophysical characterizations of thermal-stable naphthalene benzimidazoles

J Fluoresc. 2011 Jul;21(4):1565-73. doi: 10.1007/s10895-011-0845-z. Epub 2011 Jan 29.

Abstract

Microwave-assisted synthesis, photophysical and electrochemical properties of thermal-stable naphthalene benzimidazoles and naphthalimides are studied in this paper. Microwave-assisted synthesis of naphthalene benzimidazoles provide higher yields than the conventional thermal synthesis. Comparative photophysical properties of naphthalene benzimidazoles and naphthalimides are revealed that conjugation of electron-donating group onto naphthalimide moiety increases fluorescence quantum yields. Fluorophore-solvent interactions are also investigated using Lippert-Mataga equation for naphthalimides and naphthalene benzimidazoles. Thermal stabilities of naphthalene benzimidazoles are better than naphthalimides due to increased aromaticity. The experimental E(LUMO) levels of naphthalene benzimidazoles are found to be between 3.15 and 3.28 eV. Therefore, naphthalene benzimidazole derivatives consisting of anchoring groups are promising materials in organic dye sensitized solar cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry*
  • Electrochemistry
  • Fluorescence
  • Microwaves
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry*
  • Naphthalimides / chemical synthesis
  • Naphthalimides / chemistry
  • Photochemical Processes
  • Stereoisomerism
  • Temperature*

Substances

  • Benzimidazoles
  • Naphthalenes
  • Naphthalimides
  • naphthalene