An Efficient Synthesis of Quaterrylenedicarboximide NIR Dyes

J Org Chem. 2007 Dec 21;72(26):10243-6. doi: 10.1021/jo702019p. Epub 2007 Nov 29.

Abstract

Quaterrylenedicarboximides were prepared from 9-bromoperylene-3,4-dicarboximides by palladium-catalyzed coupling with 3-perylene boronic ester, followed by oxidative cyclodehydrogenation of the resulting perylene-perylenedicarboximide dyads with iron(III) chloride. The quaterrylenedicarboximides, described here, are highly photochemically and thermally stable dyes, which may be useful as green NIR dyes (lambdamax = 735 nm) and as building blocks for the synthesis of higher rylene dyes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coloring Agents / chemical synthesis*
  • Coloring Agents / chemistry
  • Imides / chemical synthesis*
  • Imides / chemistry
  • Molecular Structure
  • Perylene / analogs & derivatives*
  • Perylene / chemical synthesis
  • Perylene / chemistry
  • Spectroscopy, Near-Infrared / methods*
  • Stereoisomerism

Substances

  • Coloring Agents
  • Imides
  • Perylene