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Hydrogen-bonding controlled self-assembly

Posted on:1997-02-06Degree:Ph.DType:Dissertation
University:University of PittsburghCandidate:Yang, JiFull Text:PDF
GTID:1461390014981019Subject:Chemistry
Abstract/Summary:
Design, syntheses and characterization of two organic molecular self-assembly motifs, "2 + 2" and cyclic hexameric aggregation, have been discussed.;The crystal structures of 2-bromoisophthalic acid, 2-(p-methoxyphenyl)isophthalic acid and 5-methoxyisophthalic acid have shown the formation of hydrogen bonded ribbon structures. 5-octyloxyisophthalic acid 63 and 5-decyloxyisophthalic acid 64, however, form well-defined cyclic hexameric aggregates in the solid state. 63 and 64 show interesting crystal packing and solvent inclusion was observed in the lattices. Investigations of isophthalic acid derivatives 69 by NMR and GPC indicated that large sized aggregates formed at concentration above 10 mM in toluene and benzene. VPO results showed that the observed molecular weight of the species in solution is close to the calculated molecular weight of a hexameric complex.;2-(4-Methoxy)phenyl-5-(3,4,5-tridodecyloxy)benzyloxyisophthalic acid (85) has been synthesized. 85 is soluble in nonpolar solvents and solid-liquid extraction, variable temperature NMR and ;The crystal structures of benzene-1,3-dicarboxamidinium terephthalate, benzene-1,3 and 1,4-dicarboxamidinium have been determined and a dilution experiment has been conducted in DMSO for the complex benzene-1,3-dicarboxamidinium 5-octyloxyisophthalate.;Three 3,3...
Keywords/Search Tags:Cyclic hexameric
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