Moore, Beth L. (2014) Incorporation of amino acids into polymeric structures for use in chiral resolution, catalysis and fluorescence studies. PhD thesis, University of Warwick.

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Abstract

The general concepts of the thesis have been introduced in Chapter 1. These include the polymerization techniques that have been utilized and a background to each of the applications that have been targeted.

In Chapter 2 the synthesis of poly(tryptophan) though a polymeric scaffold synthesized via RAFT polymerization is investigated. Once synthesized, the monomer and polymer, along with previously synthesized poly(phenylalanine), are used for in the chiral resolution experiments of 1,1’-bi-2-napthol.

Chapter 3 focuses on the synthesis of a novel monomer that contains the catalytically active MacMillan catalyst synthesized from L-tyrosine. This enabled immobilization of the MacMillan catalyst into polymers prepared via RAFT polymerization. The monomeric catalyst could then be incorporated into co-polymers at pre-determined specific loadings. These polymers were then used to catalyze the Diels-Alder reaction with great effect and had the ability to be used in a pseudo-continuous process.

Chapter 4 places the monomeric MacMillan catalyst into nanogels synthesized through emulsion polymerization. The effect of having the catalyst within this unique environment was studied both through conversion and selectivity. The relatively simple synthesis allowed for the bespoke environment to be readily changed altering the amount of catalyst and co-monomer of the nanogel.

In Chapter 5 a new polymerizable L-tryptophan monomer has been synthesized and incorporated into RAFT synthesized polymers and nanogels which were synthesized through emulsion polymerization. Both of these structures fluorescent properties have been investigated; in particular the nanogels ability to function as a FRET pair to the small molecule dansyl amide has been examined. This has allowed for the effect of the structure of the nanogel on small molecule diffusion to be probed.

Item Type:	Thesis or Dissertation (PhD)
Subjects:	Q Science > QD Chemistry
Library of Congress Subject Headings (LCSH):	Amino acids, Polymerization
Official Date:	February 2014
Dates:	Date Event February 2014 Submitted
Institution:	University of Warwick
Theses Department:	Department of Chemistry
Thesis Type:	PhD
Publication Status:	Unpublished
Supervisor(s)/Advisor:	O'Reilly, Rachel K.
Sponsors:	Engineering and Physical Sciences Research Council
Extent:	xxix, 291 leaves : illustrations, charts
Language:	eng

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