Solvents effects on the self-assemblies of 5,5′-bis(3-hydroxyphenyldiazo)-dipyrromethane

5,5′-Bis(3-hydroxyphenyldiazo)-dipyrromethane, compound 3, was synthesized and its crystal structures with methanol, THF and acetone were studied by X-ray crystallography. In all three crystal structures, the 5,5′-bisdiazo-dipyrromethane still assembled into interlocked type dimers through quadruple NH⋯N hydrogen bonds. In the solid state, 3⋅3 dimers assembled into [n]cantane like structure mediated by methanol which act as hydrogen bond donor and acceptor. The 3⋅3 dimers assembled into rotaxane and broken [n]cantane like structures in the cases of THF and acetone, respectively. The solvents effects on the self-assemblies of compound 3 were also witnessed by SEM studies.