The photochemistry of indole and some derivatives
The photochemistry of indole and some derivatives
The direct and sensitised photooxidation of the important amino-acid, tryptophan is briefly reviewed with emphasis on its implication in the photoyellowing of wool. The mechanistic aspects of these photooxidations are also discussed.It has been shown that the C2-C3 double bond of tryptophan undergoes oxidative cleavage when exposed to uv radiation. An investigation of a model, 2,3-dimethylindoline, was undertaken to assess the effect of hydrogenating the C2-C3 double bond on the rate of photooxidation. A mechanism for the photodegradation was postulated. The photophysics of indole and indoline have been examined in the gas and solution phases and in various gas matrices at 10K. It was found that matrix isolation was a powerful technique for observing the triplet state and the effect of heavy atom perturbation. It was demonstrated that photodegradation of tryptophan will result in dual exponential decay behaviour. The quenching of N-acetyltryptophanamide by acrylamide, maleic anhydride, urocanic acid and l,3,5-triacroylaminohexahydro-striazine has been studied, using static and dynamic quenching techniques. The photoyellowing of merino wool samples treated with the latter three quenchers, have been investigated. The photophysics of styrene is reviewed. 2-Phenylnorbornene was chosen as a model for styrene in which the olefinic double bond is held in a rigid [2.2.1] bicyclic framework. Time resolved spectroscopy showed that twisting of the double bond was prevented. The fluorescence lifetimes of four cyclic styrenes, phenylcyclobutene, phenylcyclopentene, phenylnorbornene and indene have been compared under various experimental conditions.
University of Southampton
1980
Mant, Geoffrey Richard
(1980)
The photochemistry of indole and some derivatives.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The direct and sensitised photooxidation of the important amino-acid, tryptophan is briefly reviewed with emphasis on its implication in the photoyellowing of wool. The mechanistic aspects of these photooxidations are also discussed.It has been shown that the C2-C3 double bond of tryptophan undergoes oxidative cleavage when exposed to uv radiation. An investigation of a model, 2,3-dimethylindoline, was undertaken to assess the effect of hydrogenating the C2-C3 double bond on the rate of photooxidation. A mechanism for the photodegradation was postulated. The photophysics of indole and indoline have been examined in the gas and solution phases and in various gas matrices at 10K. It was found that matrix isolation was a powerful technique for observing the triplet state and the effect of heavy atom perturbation. It was demonstrated that photodegradation of tryptophan will result in dual exponential decay behaviour. The quenching of N-acetyltryptophanamide by acrylamide, maleic anhydride, urocanic acid and l,3,5-triacroylaminohexahydro-striazine has been studied, using static and dynamic quenching techniques. The photoyellowing of merino wool samples treated with the latter three quenchers, have been investigated. The photophysics of styrene is reviewed. 2-Phenylnorbornene was chosen as a model for styrene in which the olefinic double bond is held in a rigid [2.2.1] bicyclic framework. Time resolved spectroscopy showed that twisting of the double bond was prevented. The fluorescence lifetimes of four cyclic styrenes, phenylcyclobutene, phenylcyclopentene, phenylnorbornene and indene have been compared under various experimental conditions.
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Published date: 1980
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Local EPrints ID: 463632
URI: http://eprints.soton.ac.uk/id/eprint/463632
PURE UUID: 56454f1b-672e-4759-86dc-a48290fd462b
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Date deposited: 04 Jul 2022 20:54
Last modified: 04 Jul 2022 20:54
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Author:
Geoffrey Richard Mant
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