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

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 π-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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Wu, Wei-Ming

Contributors dc:contributor

• Zimmerman, Steven C.

• Chemistry, Biochemistry
• Chemistry, Organic

Identifier

(UMI)AAI9236630

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/72270