SUPRAMOLECULAR SYNTHESIS OF ORGANIC LAMINATES WITH AFFINITY FOR AROMATIC GUESTS - A NEW CLASS OF CLAY MIMICS

Single-crystal X-ray diffraction analysis of 25 supramolecular laminat e structures formed from reaction of trimesic acid or trimellitic acid with 2 equiv of N,N-dibenzylamine reveals an ability to incorporate a romatic guest molecules irrespective of their size and electronic natu re. The guest molecules included are nitrobenzene, anisole, veratrole, 1,4-dimethoxybenzene, 1,3,5-trimethoxybenzene, m-xylene, mesitylene, tetramethylbenzene, pentamethylbenzene, hexamethylbenzene, N,N-dibenzy lamine, naphthalene, 1-methylnaphthalene, pyrene, and ferrocene. The a cid moieties and ammonium cations reproducibly form charge-assisted 2D hydrogen-bonded layers with pendant benzyl groups above and below the layers. In the absence of guest molecules, interdigitation of benzyl groups is observed. Guest molecules interact with the laminates via a plethora of aromatic edge-to-face and face-to-face interactions. The u nit cell lengths are based upon multiples of similar to 12, x 17 x 21 Angstrom. The 12-Angstrom dimension represents the approximate interla yer separation whereas the 17 x 21 Angstrom dimensions represent the h ydrogen-bonded layer.