A concise, three-step synthesis of 1,4,8,11-substituted 2,3,9,10-tetrakis(methoxycarbonyl)pentacenes from commercially available 1,2,4,5-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 1a-c. The process was compatible with methyl, phenyl, and trimethylsilyl substituents, which have good solubility in various organic solvents.
Materials by design for sustainable solutions in the energy, medical, transport, and engineering sectors
