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

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.