Polymer-supported photosensitizers for oxidative organic transformations in flow and under visible light irradiation

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

doi:10.1021/acscatal.7b00888

Polymer-supported photosensitizers for oxidative organic transformations in flow and under visible light irradiation

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

Pure And Applied Chemistry

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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	14 Jun 2017
DOIs	https://doi.org/10.1021/acscatal.7b00888
Publication status	Published - 7 Jul 2017

Keywords

flow chemisty
free-radical polymerisation
heterogeneous photosensitizer
reactive oxygen species
singlet oxygen
visible light

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10.1021/acscatal.7b00888

Tobin-etal-ACS-Catalysis-2017-Polymer-supported-photosensitizers-for-oxidative-organicAccepted author manuscript, 669 KB

Cite this

@article{67a63a532c7143a99e63365f55bef14e,

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 chemisty, free-radical polymerisation, heterogeneous photosensitizer, reactive oxygen species, singlet oxygen, visible light",

author = "Tobin, {John M.} and McCabe, {Timothy J. D.} and Prentice, {Andrew W.} and Sarah Holzer and Lloyd, {Gareth O.} and Paterson, {Martin J.} and Valeria Arrighi and Cormack, {Peter A. G.} and Filipe Vilela",

note = "This document is the unedited Author{\textquoteright}s version of a Submitted Work that was subsequently accepted for publication in ACS Catalysis, copyright {\textcopyright} American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acscatal.7b0088",

year = "2017",

month = jul,

day = "7",

doi = "10.1021/acscatal.7b00888",

language = "English",

volume = "7",

pages = "4602--4612",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "7",

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TY - JOUR

T1 - Polymer-supported photosensitizers for oxidative organic transformations in flow and under visible light irradiation

AU - Tobin, John M.

AU - McCabe, Timothy J. D.

AU - Prentice, Andrew W.

AU - Holzer, Sarah

AU - Lloyd, Gareth O.

AU - Paterson, Martin J.

AU - Arrighi, Valeria

AU - Cormack, Peter A. G.

AU - Vilela, Filipe

N1 - This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in ACS Catalysis, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acscatal.7b0088

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 chemisty

KW - free-radical polymerisation

KW - heterogeneous photosensitizer

KW - reactive oxygen species

KW - singlet oxygen

KW - visible light

UR - http://pubs.acs.org/journal/accacs

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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Peter Cormack

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Polymer-supported photosensitizers for oxidative organic transformations in flow and under visible light irradiation

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Peter Cormack

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