LAYERED MATERIALS BY MOLECULAR DESIGN - STRUCTURAL ENFORCEMENT BY HYDROGEN-BONDING IN GUANIDINIUM ALKANESULFONATE AND ARENESULFONATE

Single crystal X-ray structures of a series of guanidinium alkane- and arenesulfonates C(NH2)(3)(+)RSO(3)(-) (R = (CH2)(x)CH3 (x = 0-3), (1S )-(+)-1O-camphor, benzene, 1-naphthalene, and 2-naphthalene) reveal se lf-assembly of the ions into unique two-dimensional hydrogen-bonded sh eets directed by hydrogen bonds between the six guanidinium protons an d the six lone electron pairs of the sulfonate oxygen atoms. The sheet s assemble in the third dimension as either single layers or bilayers with interpenetrating R groups, depending upon the steric requirements of the R groups. The observed solid-state motifs demonstrate that gua nidinium sulfonates represent a novel class of crystalline solids for the molecular-level design and synthesis of new electronic materials.