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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