Synthesis of novel heteropentacenes containing nitrogen, sulfur and oxygen or selenium

Abstract

Reactions of 2,2′-dichloro-3,3′-diquinolinyl sulfide with selected S-, O-, Se-, C- and N-nucleophiles proceeded as a hetero-ring closure to form six linear annelated pentacyclic heterocycles with a sulfur-containing central ring (1,4-dithiin, 1,4-thiazine, 1,4-thiaselenin, 1,4-oxathiin and thiopyran) in moderate to good yields. The X-ray study of selected heteropentacenes revealed that heteropentacenes, in contrast to homopentacene, are non-planar and folded along the central sulfur-heteroatom axis. The central six-membered ring is in a boat conformation.