University of Illinois Urbana-Champaign

Part I. Molecular Tweezers: Synthetic Receptors for Nucleotide Bases. Part II. Molecular Self-Assembly: Design of a Helical Aggregate

Wu, Wei-Ming

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Description

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
Issue Date
1992
Doctoral Committee Chair(s)
Zimmerman, Steven C.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(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.
Graduation Semester
1992
Type of Resource
text
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http://hdl.handle.net/2142/72270

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