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Synthesis of crescent shaped heterocyclic urea-linked foldamers

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Synthesis of crescent shaped heterocyclic urea-linked foldamers

Mousseau, James (2006) Synthesis of crescent shaped heterocyclic urea-linked foldamers. Masters thesis, Concordia University.

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Abstract

Foldamers are oligomers or polymers that have well-defined conformations in solution. The synthesis of tunable, heterocyclic, urea-linked foldamers is described. The curvatures of the foldamers can be altered by varying the heterocylic diazine (pyrazine, pyrimidine, pyridazine) or the non-heterocyclic (tolyl, o -xylyl, m -xylyl) aromatic units. Foldamers comprised of three to five aromatic groups were synthesized. Folding of these oligomers is driven by the restricted rotation along the urea bonds linking the aromatic units. This restricted rotation is caused by the additive effects of non-covalent interactions, particularly intramolecular hydrogen bonding between the urea hydrogen and the heterocyclic nitrogen atoms and steric interaction between the urea carbonyl and the toluene or xylene methyl groups. These foldamers were characterized using NMR, MALDI-TOF-MS, and FTIR. To the best of our knowledge, these are the first urea-based foldamers where curvature of the macromolecule can be easily controlled by varying either the heterocyclic or non-heterocyclic aromatic segments.

Divisions:Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry
Item Type:Thesis (Masters)
Authors:Mousseau, James
Pagination:xv, 106 leaves : ill. ; 29 cm.
Institution:Concordia University
Degree Name:M. Sc.
Program:Chemistry and Biochemistry
Date:2006
Thesis Supervisor(s):Cuccia, Louis
ID Code:9260
Deposited By:Concordia University Libraries
Deposited On:18 Aug 2011 14:47
Last Modified:01 Dec 2011 16:34
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