Supramolecular 1D assemblies of polyfluorinated arylenediamines and 18-crown-6

Abstract

Rods (1D assemblies) formed by alternate crown ether and arylenediamine molecules are the motif of the supramolecular architecture of crystals of molecular associates of 18-crown-6 with tetrafluoro-1,4- and -1,3-phenylenediamines, hexafluoro-2,6- and -2,7-naphthylenediamines. Molecules in the assemblies are arranged via H-bond predominantly between the crown ether oxygen atoms and the polyfluoroarene amino group hydrogen atoms. Influence of the amino groups mutual arrangement and the aromatic framework size on the crystal supramolecular architecture is characterized. Specific melting heats of the crystalline 1D assemblies of para- and pseudo-para-arylenediamines are higher than those of meta- and pseudo-meta-analogs; the associates having higher melting heats selectively crystallize from solutions of isomeric phenylene- or naphthylenediamine mixtures.