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Improving NMR Sensitivity: The Synthesis and SABRE Evaluation of Nicotine Isotopologues

Duckworth, William Hugh (2018) Improving NMR Sensitivity: The Synthesis and SABRE Evaluation of Nicotine Isotopologues. PhD thesis, University of York.

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Abstract

This thesis describes the development of a range of isotopically-labelled derivatives of (−)-nicotine, their subsequent hyperpolarisation by SABRE, their characterisation and the evaluation of their performance. Hyperpolarisation is a method of generating significantly enhanced magnetic resonance signals without increased sample size, scan time or prohibitively expensive improvements in equipment. The primary aim of this thesis was to develop a family of (−)-nicotine derivatives as potent SABRE substrates with a view unlocking their future biological applications in areas such as MRI. (−)-Nicotine is an important biological compound of great interest, with potent and well-documented psychoactivity. The relationship between signal enhancement, signal lifetime and a range of dependencies such as temperature, field and substrate choice are examined in detail. Results show that the interdependencies of such conditions are highly complex but follow logical patterns. Kinetic models are developed to more accurately describe the intricacies of the resulting chiral (−)-nicotine-based complexes, and they shed light on significant flaws in existing SABRE exchange models. Collectively, the synthetic 2H-labelling developments and SABRE evaluation involved no less than 23 materials. In addition, our understanding of the role 2H labelling plays in SABRE is secured.

Item Type: Thesis (PhD)
Keywords: nicotine, MRI, SABRE, hyperpolarisation, kinetics, exchange
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr William Hugh Duckworth
Date Deposited: 04 Jun 2019 13:28
Last Modified: 04 Jun 2019 13:28
URI: http://etheses.whiterose.ac.uk/id/eprint/24109

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