Self-assembly of a novel functional molecule: 1,2,4,5-tetra( p-hydroxyphenyl)benzene

Abstract

A new rigid tetraaryl-substituted benzene, 1,2,4,5-tetra( p-hydroxyphenyl)benzene (C 30H 22O 4, TetHPB), has been synthesized. Its crystalline hydrate C 30H 22O 4·2H 2O ( 1) and the inclusion compound of its anions with the tetrapropylammonium cations, [(C 30H 21O 4) 2H] −·( n-C 3H 7) 4N + ( 2), have been prepared and characterized by single crystal X-ray diffraction. The results of the structural study show that the four peripheric para hydroxyl benzene rings of the TetHPB molecules twist around the aryl–aryl bonds and adopt an X-shaped configuration thus avoiding steric congestion. In the crystal structure of 1 hydrogen-bonded TetHPB chains are connected to a 3D architecture by hydrogen bonds mediated through the solvent water molecules and by C–H… π interactions. In compound 2, the TetHPB anions construct an anionic arrangement based on O–H…O hydrogen bonds. The resulting host contains cavities which accommodate the tetrapropylammonium cations, thus forming a channel-like inclusion compound. These results demonstrate that TetHPB molecules allow to construct hydrogen-bonded networks with cavities; co-crystallized water molecules may cooperate in the formation of these extended structures.