Three-Step Synthesis of End-Substituted Pentacenes

摘要

A concise, three-step synthesis of 1,4,8,11-substituted 2,3,9,-10-tetrakis(methoxycarbonyl)pentacenes from commercially available l,2,4,5-tetrakis(bromomethyl)benzene was established. Efficient alkynylation, followed by formation of four fused rings via a zirconacyclopentadiene intermediate, and then oxidation with DDQ gave pentacenes la—c. The process was compatible with methyl, phenyl, and trimethylsilyl substituents, which have good solubility in various organic solvents.