Dianiline-diphenol molecular complexes based on supraminol recognition

Abstract

Dianilines and diphenols form well-defined crystalline molecular complexes that arise from complementary O-H···N and N-H···O recognition. The crystal structures of four such 1:1 complexes 1, 2, 3 and 4 based on diphenylmethane frameworks are reported and discussed. Three supramolecular synthons are found, the N(H)O based square motif and infinite chain, already reported, and a new cyclohexane chair consisting of N(H)O, O-H···O and N-H···N hydrogen bridges. The replacement of a -CH₂- group by an S-atom leads in two cases to little change in the crystal structure and in another to a complete change. It is possible that the dianiline component plays a more important role in molecular recognition in these complexes than does the diphenol component.