The structure of 7,14-dicarbonylethoxyacenaphth[l,2-k]-fluoranthene and its tetracyanoquinodimethane charge transfer complex

A molecular mechanics simulation of the structure of 7,14-dicarbonylethoxyacenaphthl,2-k]fluoranthene,1, indicated a preferred geometry for the hindered substituents in which the carbonyl groups were constrained to an anti conformation because of the steric hindrance associated with the in-plane buttressing hydrogen atoms. X-ray crystallographic analysis of1 verifies the correctness of the computation. Compound1 and tetracyanoquinodimethane,2, form a charge transfer complex, and a crystal structure analysis shows a slightly offset, nearly parallel arrangement of the acceptor with the cloud of the donor. The interplanar distance of 3.45 Å between acceptor and donor lies within the statistical limits of the interplanar distance of complexes formed between2 and a variety of PAH donors. The steric hindrance caused by the substituents in1 appears to offer only minimal interference to the formation of the complex.