Polymer-Supported Photosensitizers for Oxidative Organic Transformations in Flow and Under Visible Light Irradiation

John Tobin; Timothy McCabe; Andrew Prentice; Sarah Holzer; Gareth O. Lloyd; Martin J. Paterson; Valeria Arrighi; Peter Cormack; Filipe Vilela

doi:10.1021/acscatal.7b00888

Polymer-Supported Photosensitizers for Oxidative Organic Transformations in Flow and Under Visible Light Irradiation

John Tobin, Timothy McCabe, Andrew Prentice, Sarah Holzer, Gareth O. Lloyd, Martin J. Paterson, Valeria Arrighi, Peter Cormack, Filipe Vilela

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Abstract

A 2,1,3-benzothiadiazole (BTZ)–based vinyl crosslinker was synthesized and copolymerized with large excesses of styrene using free radical polymerization to deliver heterogeneous triplet photosensitizers in three distinct physical formats: gels, beads and monoliths. These photosensitizers were employed for the production of singlet oxygen (1O2) and for the aerobic hydroxylation of aryl boronic acids via superoxide radical anion (O2˙-) whereby the materials demonstrated good chemical and photo stability. BTZ-containing beads and monoliths were exploited as photosensitizers in a commercial flow reactor, and 1O2 production was also demonstrated using direct sunlight irradiation, with a conversion rate comparable to the rates achieved when using a 420 nm LED module as the source of photons.

Original language	English
Pages (from-to)	4602–4612
Number of pages	11
Journal	ACS Catalysis
Volume	7
Issue number	7
Early online date	2 Jun 2017
DOIs	https://doi.org/10.1021/acscatal.7b00888
Publication status	Published - 7 Jul 2017

Keywords

flow chemistry
free-radical polymerization
heterogeneous photosensitizer
reactive oxygen species
singlet oxygen
visible light

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10.1021/acscatal.7b00888

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© 2017 American Chemical Society
Accepted author manuscript, 842 KBLicence: All Rights Reserved

Filipe Vilela
- F.Vilelahw.acuk
- School of Engineering & Physical Sciences - Assistant Professor
- School of Engineering & Physical Sciences, Institute of Chemical Sciences - Assistant Professor
Person: Academic (Research & Teaching)

Cite this

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title = "Polymer-Supported Photosensitizers for Oxidative Organic Transformations in Flow and Under Visible Light Irradiation",

abstract = "A 2,1,3-benzothiadiazole (BTZ)–based vinyl crosslinker was synthesized and copolymerized with large excesses of styrene using free radical polymerization to deliver heterogeneous triplet photosensitizers in three distinct physical formats: gels, beads and monoliths. These photosensitizers were employed for the production of singlet oxygen (1O2) and for the aerobic hydroxylation of aryl boronic acids via superoxide radical anion (O2˙-) whereby the materials demonstrated good chemical and photo stability. BTZ-containing beads and monoliths were exploited as photosensitizers in a commercial flow reactor, and 1O2 production was also demonstrated using direct sunlight irradiation, with a conversion rate comparable to the rates achieved when using a 420 nm LED module as the source of photons.",

keywords = "flow chemistry, free-radical polymerization, heterogeneous photosensitizer, reactive oxygen species, singlet oxygen, visible light ",

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year = "2017",

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T1 - Polymer-Supported Photosensitizers for Oxidative Organic Transformations in Flow and Under Visible Light Irradiation

AU - Tobin, John

AU - McCabe, Timothy

AU - Prentice, Andrew

AU - Holzer, Sarah

AU - Lloyd, Gareth O.

AU - Paterson, Martin J.

AU - Arrighi, Valeria

AU - Cormack, Peter

AU - Vilela, Filipe

PY - 2017/7/7

Y1 - 2017/7/7

N2 - A 2,1,3-benzothiadiazole (BTZ)–based vinyl crosslinker was synthesized and copolymerized with large excesses of styrene using free radical polymerization to deliver heterogeneous triplet photosensitizers in three distinct physical formats: gels, beads and monoliths. These photosensitizers were employed for the production of singlet oxygen (1O2) and for the aerobic hydroxylation of aryl boronic acids via superoxide radical anion (O2˙-) whereby the materials demonstrated good chemical and photo stability. BTZ-containing beads and monoliths were exploited as photosensitizers in a commercial flow reactor, and 1O2 production was also demonstrated using direct sunlight irradiation, with a conversion rate comparable to the rates achieved when using a 420 nm LED module as the source of photons.

AB - A 2,1,3-benzothiadiazole (BTZ)–based vinyl crosslinker was synthesized and copolymerized with large excesses of styrene using free radical polymerization to deliver heterogeneous triplet photosensitizers in three distinct physical formats: gels, beads and monoliths. These photosensitizers were employed for the production of singlet oxygen (1O2) and for the aerobic hydroxylation of aryl boronic acids via superoxide radical anion (O2˙-) whereby the materials demonstrated good chemical and photo stability. BTZ-containing beads and monoliths were exploited as photosensitizers in a commercial flow reactor, and 1O2 production was also demonstrated using direct sunlight irradiation, with a conversion rate comparable to the rates achieved when using a 420 nm LED module as the source of photons.

KW - flow chemistry

KW - free-radical polymerization

KW - heterogeneous photosensitizer

KW - reactive oxygen species

KW - singlet oxygen

KW - visible light

U2 - 10.1021/acscatal.7b00888

DO - 10.1021/acscatal.7b00888

M3 - Article

SN - 2155-5435

VL - 7

SP - 4602

EP - 4612

JO - ACS Catalysis

JF - ACS Catalysis

IS - 7

ER -

Polymer-Supported Photosensitizers for Oxidative Organic Transformations in Flow and Under Visible Light Irradiation

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