New trigonal lattice hosts: stoicheiometric crystal inclusions of laterally trisubstituted benzenes—X-ray crystal structure of 1,3,5-tris-(4-carboxyphenyl)benzene·dimethylformamide

Abstract

New host molecules with a central 1,3,5-trisubstituted benzene ring and rigidly attached lateral arms composed of aryl or arylethynyl and extra functional groups are reported. They are shown to give more than thirty clathrates with a wide variety of organic solvents comprising alicyclic, aromatic, heterocyclic, dipolar aprotic, and protic molecules. Inclusion selectivities and stoicheiometries of the different clathrates are discussed. The crystal structure of (2a)·dimethylformamide (DMF)(1:3) inclusion compound has been determined from single-crystal X-ray diffraction. The crystals show R symmetry. There are six host and eighteen guest molecules in the hexagonal unit cell with a=b= 23.160(9) and c= 11.812(3)Å. The final linear R is 0.082 for 1 518 unique reflections. The host molecules adopts a propeller conformation with perfect three-fold symmetry and acts as a donor in hydrogen bonds to three DMF molecules. In the crystal structure the host–guest units are arranged stack-wise.