Anthracen- und Anthrachinon-Oligomere mit ortho-Cyclophanverknüpfung durch wiederholte Diels-Alder-Reaktion von 1,2,5,6-Tetra-exo-methylencyclooctan

Abstract

The design of efficient organic electron acceptors requires oligomeric and polymeric hydrocarbons in which separate redox-active units are connected in a sterically variable fashion. A broad series of suitable model compounds are synthesized via Diels-Alder reaction of the «bis-diene» 1,2,5,6-tetra-exo-methylenecyclooctane and the «bis-dienophile» p-benzoquinone (or the «mono-dienophile» 1,4-naphthoquinone). The method provides ortho-cyclophane systems with anthracene or anthraquinone units. Repetitive Diels-Alder reactions lead to structurally related oligomers and polymers.