Indolo[2,3-b]carbazole synthesized from a double-intramolecular Buchwald-Hartwig reaction: its application for a dianchor DSSC organic dye

Org Lett. 2014 Jun 20;16(12):3176-9. doi: 10.1021/ol500663b. Epub 2014 Jun 11.

Abstract

A new synthetic strategy for indolo[2,3-b]carbazole via a double-intramolecular Buchwald-Hartwig reaction has been established. The N-alkylated indolo[2,3-b]carbazole then was adopted as the geometry-fixed core for the synthesis of a new molecule (ICZDTA) bearing two bithiophene π-bridged 2-cyanoacrylic acid groups as the bidentate anchor. The bidentate anchoring together with efficient HOMO (indolo[2,3-b]carbazole) → LUMO (TiO2 nanocluster) electron transfer leads to the successful development of ICZDTA-based DSSC with a power conversion efficiency of 6.02%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Coloring Agents / chemical synthesis*
  • Coloring Agents / chemistry
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Models, Molecular
  • Molecular Structure

Substances

  • 5,7-dihydroindolo(2,3-b)carbazole
  • Carbazoles
  • Coloring Agents
  • Indole Alkaloids