A Three-Dimensional Channel Supramolecular Architecture Based on 3-Amino-2-(4-dimethylaminophenyldiazenyl)-1-phenylbut-2-en-1-one and Aromatic Guests

If crystallized from aromatic solvents (benzene, toluene, p-xylene, chlorobenzene), 3-amino-2-(4-dimethylaminophenyldiazenyl)-1-phenylbut-2-en-1-one (1) forms a three-dimensional supramolecular H-bonding network with molecular channels of approximately cylindrical shape in which the solvent molecules are placed in a defined manner. The aromatic molecules are bound with the molecules of the network by means of weak intermolecular interactions of varying nature. The X-ray structures provide detailed information on the binding motifs that consist of C−H···O and C−H···π bonds between the aromatic solvent molecules and the benzoyl moiety of 1. The motifs are identical in all the four inclusion compounds analyzed showing the robustness of this supramolecular synthon. Accordingly, the crystals adopt isostructural arrangements favored by the mutual orientation of the host molecules of 1 that make identical helical catemers by means of strong N−H···O intermolecular hydrogen bonds. Thermal stability of the inclusion compounds of compound 1 with benzene, toluene, p-xylene, and m-xylene has been studied by means of differential scanning calorimetry and thermogravimetric analysis methods.