Design, synthesis and application of hydrogen bond directed molecular receptors and supramolecular self-assemblies

Date of Award




Degree Name

Doctor of Philosophy (Ph.D.)



First Committee Member

K. C. Russell, Committee Chair


Among all the non-covalent interaction, the strength, directionality and feasibility place the hydrogen bonding the center of supramolecular chemistry. This dissertation has been focused on the design, synthesis and applications of hydrogen bonding directed molecular receptors and supramolecular self-assemblies.To mimic the partial catalytic function of enzymes, a supramolecular complex was designed and synthesized. Through the four-point hydrogen bonding between the ligand and the receptor binding cleft, the reactive ligand was expected to undergo conformational change to a structure favorable for intramolecular interactions to occur. Although the receptor has been shown to bind with model ligands in the proposed manner, the complex did not exhibit desired catalytic function when applied on a reactive ligand.Hydrogen bonding self-assembly at the air-water interface has attracted extensive interest recently. The present studies are aimed at the design and creation of well-defined supramolecular structures in 2-dimension. Important aspects on the molecular and supramolecular structures of the hydrogen bonding networks formed between triaminotriazine amphiphiles and complementary components at the air-water interface have been revealed by different physico-chemical studies. Using this complementary hydrogen bonding self-assembly, polydiacetylenes with unique chromatic properties were discovered. Furthermore, a self-assembly through the urea functionalities has also exhibited the strength and power of hydrogen bonding in the control of material properties through supramolecular chemistry approach. Most importantly, hydrogen bonding self-assembly in 2-dimension has lead to the discovery of a completely unconventional approach in the future design of Langmuir and Langmuir-Blodgett films.


Chemistry, Organic; Chemistry, Physical

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