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Title:Part I. Molecular Tweezers: Synthetic Receptors for Nucleotide Bases. Part II. Molecular Self-Assembly: Design of a Helical Aggregate
Author(s):Wu, Wei-Ming
Doctoral Committee Chair(s):Zimmerman, Steven C.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Biochemistry
Chemistry, Organic
Abstract:In Part I, the design, syntheses, and complexation studies of molecular tweezers containing active site carboxylic acids are discussed. The strength, nature, stoichiometry, and geometry of the complex between molecular tweezer 28 and 9-propyladenine was studied. The cooperativity of hydrogen bonding and $\pi$-stacking interactions resulted in the efficient complexation of 9-propyladenine by 28, a association constant of 25,000 M$\sp{-1}$ was measured. The nucleoside selectivity of 28 was also studied. Studies suggested that the unique microenvironment provided in 28 altered the preference of the carboxylic acid for nucleotide bases and for the hydrogen bonding sites in adenine.
In Part II, principles for biological and biomimetic molecular self-assembly are discussed. A novel strategy in the design of helical assemblies is reported. Progress in the syntheses of the two heterocyclic building blocks to form a helical aggregate is discussed.
Issue Date:1992
Description:154 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1992.
Other Identifier(s):(UMI)AAI9236630
Date Available in IDEALS:2014-12-17
Date Deposited:1992

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