Synthesis of Perylene-3,4,9,10-tetracarboxylic Acid Derivatives Bearing Four Different Substituents at the Perylene Core

Rajeev K. Dubey*, Nick Westerveld, Stephen J. Eustace, E.J.R. Sudholter, Ferdinand C. Grozema, Wolter F. Jager

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

8 Citations (Scopus)

Abstract

Nucleophilic aromatic substitution reactions on 1,7-dibromoperylene-3,4,9,10-tetracarboxylic monoimide dibutylester, using phenol and pyrrolidine reagents, have been exploited to synthesize perylenes with four different substituents at the perylene core. The first substitution is always regiospecific at the imide-activated 7-position. A second substitution reaction does not always replace the bromine at C-1, but may replace a phenol substituent at the highly activated 7-position. Exploiting this reactivity pattern, a "mixed" 1,7-diphenoxy, 1,7-dipyrrolidinyl, and two 1-phenoxy-7-pyrrolidinyl derivatives have been synthesized.

Original languageEnglish
Pages (from-to)5648-5651
Number of pages4
JournalOrganic Letters
Volume18
Issue number21
DOIs
Publication statusPublished - 4 Nov 2016

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