Synthesis and structural properties of hydrogen-bonded triphenylenes and bent acenes.

摘要

This thesis describes the synthesis and characterization of two classes of molecules. First, discotic liquid crystals with either benzene or triphenylene cores were synthesized with three peripheral amide groups for intermolecular hydrogen-bonding. For the benzene-core molecules, a desymmetrized synthesis allowed the preparation and characterization of hydrogen-bonded oligomers. In the triphenylene-core molecules different substituents were used to change the strength of association in solution and the pi-pi distance in bulk, which were determined with NMR analysis and X-ray diffraction, respectively. Second, simple, substituted linear acenes were synthesized and characterized by x-ray crystallography. The drastic degree of bending of the acene core in some molecules has implications for the mechanism of nanotube formation.