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UBC Theses and Dissertations

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UBC Theses and Dissertations

Studies of supramolecular chemistry through Schiff-base chemistry Jiang, Jian


This thesis describes the synthesis, characterization, and host-guest studies of a series of Schiff-base macrocycles. New [2+2] Schiff-base macrocycles were prepared by Schiff-base condensation. These macrocycles were shown to be wide-mouthed supramolecular hosts that can include organic cations such as pyridinium, paraquat and ammonium derivatives. A new kind of donor-acceptor-donor 3-in-1 complex was obtained in solution by combining macrocycle, cyclobis(paraquat-p-phenylene) and tetrathiafulvalene. Variations of these [2+2] Schiff-base macrocycles were prepared by modifying the substituents of the diformyl diol unit. In this way naphthalene-based macrocycles that undergo keto-enamine tautomerization were synthesized. These macrocycles can also combine with organic cations to form host-guest complex. The naphthalene-based [2+2] macrocycles can form lyotropic liquid crystals in chloroform and 1,2-dichloroethane. From the polarizing optical microscopy, it is proposed that the mesophases are lyotropic nematic liquid crystals based on a bilayer structure. A further study of these macrocycles shows that the host-guest complex can also form a lyotropic liquid crystalline phase. Covalently-linked macrocycles with isosceles triangle shapes were prepared by Schiff-base condensation. The molecular isosceles triangles proved to also be supramolecular hosts for pyridinium and ammonium cations, based on ¹H NMR, 2D-ROESY NMR, and mass spectrometry studies. In addition to the Schiff-base macrocycles, conjugated Schiff-base containing oligomers were synthesized via Gilch polymerization methods. The oligomers were characterized by gel permeation chromatography (GPC), thermogravimetric analysis (TGA) and UV-Vis spectroscopy. For further proof of the oligomeric structure, a model compound was prepared by the Wittig reaction.

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