The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma

A set of highly fluorescent probes based on diphenylisobenzofuran (DPBF) have been synthesized and applied in a plasma COST jet for the detection of singlet oxygen (1O2), a reactive species vital for both synthetic applications and as a marker for cytotoxicity. The mechanistic understanding of singl...

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Main Author:	James Fuster
Format:	Default Thesis
Published:	2022
Subjects:	Other chemical sciences not elsewhere classified Chemistry Plasma Fluorescence Isobenzofuran Adamantylidene Singlet oxygen reactive oxygen species Chemical Sciences not elsewhere classified
Online Access:	https://dx.doi.org/10.26174/thesis.lboro.19086059.v1
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id	rr-article-19086059
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spelling	rr-article-190860592022-02-03T11:50:10Z The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma James Fuster (3187338) Other chemical sciences not elsewhere classified Chemistry Plasma Fluorescence Isobenzofuran Adamantylidene Singlet oxygen reactive oxygen species Chemical Sciences not elsewhere classified A set of highly fluorescent probes based on diphenylisobenzofuran (DPBF) have been synthesized and applied in a plasma COST jet for the detection of singlet oxygen (1O2), a reactive species vital for both synthetic applications and as a marker for cytotoxicity. The mechanistic understanding of singlet oxygen is limited due to its short lifetime (14 μs in ethanol). The research in this thesis showed that the highest concentration of singlet oxygen produced in plasma (150 V) was achieved using a 0.75% admixture of oxygen. The addition of electron donating groups (EDGs) within the aromatic ring illicited a faster probe response compared to DPBF. The utilisation of Hammett plots revealed that the mechanism for reacting with singlet oxygen was dependent on both the probe’s inductive and resonance electronic properties in a 60:40 ratio. This important data indicates that the reaction of DPBF with singlet oxygen undegoes a more complicated mechanism than the commonly accepted concerted [4+2] Diels-Alder cycloaddition and enables the potential designs of more reactive probes. 2022-02-03T11:50:10Z Text Thesis 10.26174/thesis.lboro.19086059.v1 https://figshare.com/articles/thesis/The_synthesis_of_Diarylisobenzofuran_and_Adamantylidene_probes_for_the_selective_detection_of_singlet_oxygen_in_plasma/19086059 CC BY-NC-ND 4.0
institution	Loughborough University
collection	Figshare
topic	Other chemical sciences not elsewhere classified Chemistry Plasma Fluorescence Isobenzofuran Adamantylidene Singlet oxygen reactive oxygen species Chemical Sciences not elsewhere classified
spellingShingle	Other chemical sciences not elsewhere classified Chemistry Plasma Fluorescence Isobenzofuran Adamantylidene Singlet oxygen reactive oxygen species Chemical Sciences not elsewhere classified James Fuster The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma
description	A set of highly fluorescent probes based on diphenylisobenzofuran (DPBF) have been synthesized and applied in a plasma COST jet for the detection of singlet oxygen (1O2), a reactive species vital for both synthetic applications and as a marker for cytotoxicity. The mechanistic understanding of singlet oxygen is limited due to its short lifetime (14 μs in ethanol). The research in this thesis showed that the highest concentration of singlet oxygen produced in plasma (150 V) was achieved using a 0.75% admixture of oxygen. The addition of electron donating groups (EDGs) within the aromatic ring illicited a faster probe response compared to DPBF. The utilisation of Hammett plots revealed that the mechanism for reacting with singlet oxygen was dependent on both the probe’s inductive and resonance electronic properties in a 60:40 ratio. This important data indicates that the reaction of DPBF with singlet oxygen undegoes a more complicated mechanism than the commonly accepted concerted [4+2] Diels-Alder cycloaddition and enables the potential designs of more reactive probes.
format	Default Thesis
author	James Fuster
author_facet	James Fuster
author_sort	James Fuster (3187338)
title	The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma
title_short	The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma
title_full	The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma
title_fullStr	The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma
title_full_unstemmed	The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma
title_sort	synthesis of diarylisobenzofuran and adamantylidene probes for the selective detection of singlet oxygen in plasma
publishDate	2022
url	https://dx.doi.org/10.26174/thesis.lboro.19086059.v1
_version_	1796461228192694272

The synthesis of Diarylisobenzofuran and Adamantylidene probes for the selective detection of singlet oxygen in plasma

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