Synthesis and Properties of a Decacyclene Monoimide and a Naphthalimide Derivative as Three-Dimensional Acceptor-Donor-Acceptor Systems.

A method involving the Diels-Alder (DA) cycloaddition of diacenaphtheno[1,2-b;1',2'-d]thiophenes (DATs) with N-alkylacenaphthylene-5,6-dicarboximides (AIs) was developed to synthesize decacyclene monoimides (DCMIs). The reactions generate the corresponding 1:2 adducts (BAIAs) as major products together with 1:1 adducts (the DCMIs). The molecular structure of BAIAb (N-octyl derivative) was unambiguously assigned as the bis-adduct having an endo,endo spatial disposition of the two acenaphthylene-5,6-dicarboximide moieties by using X-ray crystallographic analysis.