6533b825fe1ef96bd1281d74

RESEARCH PRODUCT

Band-Shaped Structures by Repetitive Cycloaddition Reactions of Benzo[1,2-b:4,5-b′]bisthiete

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description

Benzo[1,2-b:4,5-b′]bisthiete (1) undergoes stepwise thermal opening of the 4-membered rings, thereby generating two highly reactive 8π systems (Scheme 1). In the presence of 1,4-dihydro-1,4-epoxynaphthalenes 2, the dithiaheptacene derivatives 3 are formed, dehydration of which leads to the compounds 4 and 5 (Scheme 2). Repetitive cycloaddition reactions of 1 with the twofold 2π component 11 (Scheme 3) yield the oligomers 15 with statistically bent (and possibly cyclic) structures (Schemes 4 and 5). While 15 and the related oligomers 14 are freely soluble in many organic solvents, the dehydrated systems 16 (Scheme 6) are totally insoluble.