Three-step synthesis of end-substituted pentacenes.
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.
Stone
Matthew T
MT
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K. matthew.stone@chem.ox.ac.uk
Anderson
Harry L
HL