Stable phenylene- and biphenylene-bis(isobenzofuran)s related to diphenylisobenzofuran

A series of phenyl-substituted bis(isobenzofuran)s in which the furan moieties are linked by 1,3-phenylene, 1,4-phenylene, or 4,4′-biphenylene linkers have been prepared in only two steps. They are comparable to diphenylisobenzofuran in their absorption and luminescent properties, their electrochemistry, and their reactivity. Their degree of similarity to diphenylisobenzofuran was found to depend significantly on the nature of the linking group. Diels–Alder reaction of the title compounds and subsequent aromatization gave very rapid access to penta- or hexa-aryl products.