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. Key words: isobenzofuran, diphenylisobenzofuran, fluorescence, UV spectroscopy, electrochemistry, pentaphenyl, hexaphenyl. On a prepare, par des reactions n'impliquant que deux etapes, une serie de bis(isobenzofuranes) substitues par un groupe phenyle dans lesquels les portions furanes sont liees 738par des troncons 1,3-phenylene, 1,4-phenylene ou 4,4'-biphenylene. Par leurs proprietes d'absorption et de luminescence, d'electrochimie et de reactivite, ces produits se comparent au diphenylisobenzofurane. On a observe que leur degre de similarite avec le diphenylisobenzofurane depend beaucoup de la nature du groupe qui les relie. La reaction de Diels-Alder des composes mentionnes dans le titre et l'aromatisation subsequente des produits obtenus donne un acces tres rapide aux produits penta- ou hexaryles. Mots-cles : isobenzofurane, diphenylisobenzofurane, fluorescence, spectroscopie UV, electrochimie, pentaphenyle, hexaphenyle. [Traduit par la Redaction]
Commercially available 1,3-diphenylisobenzofuran (1, Fig. 1) has found wide application in the identification of reactive olefins, as an analytical tool for measuring the rate of singlet-oxygen generation and is of [...]