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

• Published in: Journal of molecular structure 2013-01, Vol.1031 (16), p.85-90
• Main Authors: Yin, Zhenming, Wang, Min, Wang, Wuyan, Wang, Xiuguang
• Format: Article
• Language: English
• Subjects: 5,5′-Bis(3-hydroxyphenyldiazo)-dipyrromethane; Acetone; Crystal engineering; crystal structure; hydrogen bonding; methanol; scanning electron microscopy; solvents; Solvents effects; Topology; X-ray diffraction
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2012.07.015

► 5,5′-bis(3-hydroxyphenyldiazo)-dipyrromethane was synthesized. ► The 5,5′-bisdiazo-dipyrromethane still assembled into interlocked type dimers through quadruple N-H…N hydrogen bonds. ► [n]cantane, rotaxane and broken [n]cantane like structures were obtained from the self-assemblies of the dimers. ► The solvents effects on the self-assemblies were also witnessed by SEM studies. 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.