Synthesis of regioisomerically pure 1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid derivatives

J Org Chem. 2014 Jul 18;79(14):6655-62. doi: 10.1021/jo501180a. Epub 2014 Jul 9.

Abstract

The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrates / chemical synthesis*
  • Butyrates / chemistry
  • Molecular Structure
  • Perylene / analogs & derivatives*
  • Perylene / chemical synthesis*
  • Perylene / chemistry
  • Stereoisomerism

Substances

  • 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester
  • Butyrates
  • Perylene