Realising the potential of infrared microscopy in combinatorial chemistry
Realising the potential of infrared microscopy in combinatorial chemistry
In combinatorial chemistry, infrared microscopy has been synonymous with aiding the optimisation of solid-phase reaction protocols, as well as providing invaluable information regarding the diffusion characteristics of a wide range of polymeric supports. In this project, infrared microscopy is used to interrogate the functional group distribution of chloromethylated polystyrene (CPS) beads after coupling with 4-cyanophenol, an IR-tagging agent. This characterisation approach provided evidence for homogeneous site distributions, as well as providing a unique insight into the chemical reactivity and accessibility of reagents in highly cross-linked CPS beads. A IR-microscope fitted with a linear pixel-array detector was also used to create spatially resolved multi-layered IR-images of a large collection of polymer beads supporting carbonyl and nitrile monomers. Strategies for obtaining high quality spectra from both imaging and mapping IR-microscopes without compromising on sample area, analysis time, or spatial resolution are also discussed.
The last decade has also seen considerable interest in developing miniaturised IR-flow cells for tandem on-line separation and IR-identification of synthetic compounds. In this project, micro-litre volume flow cells were fabricated without the need for expensive microfabrication techniques (under patent review by the University of Southampton, Sept 2003). The flow cell was hyphenated with an IR-microscope and HPLC-pump and was used to record the IR-spectra of a series of 3-alkylamino-iidazo[1,2-α]pyridines and pyrazines using stopped flow-injection techniques.
The multi-component synthesis of 3-alkylamino-imidazo[1,2-α]pyrimidines also gave rise to the unexpected synthesis of the 2-alkylamino-imidazo[1,2-α]pyrimidines. The structures of both derivatives were confirmed by X-ray crystallography and a mechanistic rationale for their formation was proposed.
University of Southampton
2004
Mandair, Gurjit S
(2004)
Realising the potential of infrared microscopy in combinatorial chemistry.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
In combinatorial chemistry, infrared microscopy has been synonymous with aiding the optimisation of solid-phase reaction protocols, as well as providing invaluable information regarding the diffusion characteristics of a wide range of polymeric supports. In this project, infrared microscopy is used to interrogate the functional group distribution of chloromethylated polystyrene (CPS) beads after coupling with 4-cyanophenol, an IR-tagging agent. This characterisation approach provided evidence for homogeneous site distributions, as well as providing a unique insight into the chemical reactivity and accessibility of reagents in highly cross-linked CPS beads. A IR-microscope fitted with a linear pixel-array detector was also used to create spatially resolved multi-layered IR-images of a large collection of polymer beads supporting carbonyl and nitrile monomers. Strategies for obtaining high quality spectra from both imaging and mapping IR-microscopes without compromising on sample area, analysis time, or spatial resolution are also discussed.
The last decade has also seen considerable interest in developing miniaturised IR-flow cells for tandem on-line separation and IR-identification of synthetic compounds. In this project, micro-litre volume flow cells were fabricated without the need for expensive microfabrication techniques (under patent review by the University of Southampton, Sept 2003). The flow cell was hyphenated with an IR-microscope and HPLC-pump and was used to record the IR-spectra of a series of 3-alkylamino-iidazo[1,2-α]pyridines and pyrazines using stopped flow-injection techniques.
The multi-component synthesis of 3-alkylamino-imidazo[1,2-α]pyrimidines also gave rise to the unexpected synthesis of the 2-alkylamino-imidazo[1,2-α]pyrimidines. The structures of both derivatives were confirmed by X-ray crystallography and a mechanistic rationale for their formation was proposed.
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Published date: 2004
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Local EPrints ID: 465317
URI: http://eprints.soton.ac.uk/id/eprint/465317
PURE UUID: 79563a05-24b6-4f41-a415-1f1a8048dab4
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Date deposited: 05 Jul 2022 00:37
Last modified: 05 Jul 2022 00:37
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Author:
Gurjit S Mandair
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