Palladium-catalyzed tandem N-H/C-H arylation: regioselective synthesis of N-heterocycle-fused phenanthridines as versatile blue-emitting luminophores

Org Biomol Chem. 2013 Dec 7;11(45):7966-77. doi: 10.1039/c3ob41760c. Epub 2013 Oct 22.

Abstract

A general and highly regioselective synthetic protocol for structurally diverse N-heteroaryl-fused phenanthridines has been developed. Varieties of fluorescence molecules comprising imidazole-fused, benzoimidazole-fused, indole-fused and pyrrole-fused phenanthridines were obtained by this modular approach, some of which exhibit excellent blue-emitting performance, high quantum yields, long fluorescence lifetimes, interesting electrochemical properties, and thermal stabilities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Electrochemical Techniques
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Luminescent Measurements
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / chemistry
  • Stereoisomerism
  • Temperature
  • Time Factors

Substances

  • Fluorescent Dyes
  • Heterocyclic Compounds
  • Organometallic Compounds
  • Phenanthridines
  • Palladium