4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

Dominic Taylor; Thomas Malcomson; Adilet Zhakeyev; Shengxian Cheng; Georgina M. Rosair; Jose Marques-Hueso; Zhengtao Xu; Martin J. Paterson; Scott J. Dalgarno; Filipe Vilela

doi:10.1039/D2QO01316A

4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

Dominic Taylor, Thomas Malcomson, Adilet Zhakeyev, Shengxian Cheng, Georgina M. Rosair, Jose Marques-Hueso, Zhengtao Xu, Martin J. Paterson, Scott J. Dalgarno^*, Filipe Vilela^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

Electron donor-acceptor (D-A) systems based on the benzo[c][1,2,5]thiadiazole (BTZ) motif have been extensively researched for use in photovoltaics or as fluorescent sensors. However, their use as potential visible-light organophotocatalysts has not received any in-depth study. Here we report the synthesis, characterisation, and application of a library of 26 D-A compounds based on the BTZ group. By varying the donor groups whilst keeping the BTZ acceptor group the same, we have been able to systematically modify the photocatalyst's optoelectronic and photophysical properties. These photocatalysts were then validated using a Minisci-type decarboxylative alkylation of electron deficient heteroarenes as a test reaction under both batch and continuous flow conditions.

Original language	English
Pages (from-to)	5473-5484
Number of pages	12
Journal	Organic Chemistry Frontiers
Volume	9
Issue number	20
Early online date	19 Aug 2022
DOIs	https://doi.org/10.1039/D2QO01316A
Publication status	Published - 21 Oct 2022

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@article{14753793e82a49258dccdb8730f3b166,

title = "4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts",

abstract = "Electron donor-acceptor (D-A) systems based on the benzo[c][1,2,5]thiadiazole (BTZ) motif have been extensively researched for use in photovoltaics or as fluorescent sensors. However, their use as potential visible-light organophotocatalysts has not received any in-depth study. Here we report the synthesis, characterisation, and application of a library of 26 D-A compounds based on the BTZ group. By varying the donor groups whilst keeping the BTZ acceptor group the same, we have been able to systematically modify the photocatalyst's optoelectronic and photophysical properties. These photocatalysts were then validated using a Minisci-type decarboxylative alkylation of electron deficient heteroarenes as a test reaction under both batch and continuous flow conditions.",

author = "Dominic Taylor and Thomas Malcomson and Adilet Zhakeyev and Shengxian Cheng and Rosair, {Georgina M.} and Jose Marques-Hueso and Zhengtao Xu and Paterson, {Martin J.} and Dalgarno, {Scott J.} and Filipe Vilela",

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month = oct,

day = "21",

doi = "10.1039/D2QO01316A",

language = "English",

volume = "9",

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T1 - 4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

AU - Taylor, Dominic

AU - Malcomson, Thomas

AU - Zhakeyev, Adilet

AU - Cheng, Shengxian

AU - Rosair, Georgina M.

AU - Marques-Hueso, Jose

AU - Xu, Zhengtao

AU - Paterson, Martin J.

AU - Dalgarno, Scott J.

AU - Vilela, Filipe

PY - 2022/10/21

Y1 - 2022/10/21

N2 - Electron donor-acceptor (D-A) systems based on the benzo[c][1,2,5]thiadiazole (BTZ) motif have been extensively researched for use in photovoltaics or as fluorescent sensors. However, their use as potential visible-light organophotocatalysts has not received any in-depth study. Here we report the synthesis, characterisation, and application of a library of 26 D-A compounds based on the BTZ group. By varying the donor groups whilst keeping the BTZ acceptor group the same, we have been able to systematically modify the photocatalyst's optoelectronic and photophysical properties. These photocatalysts were then validated using a Minisci-type decarboxylative alkylation of electron deficient heteroarenes as a test reaction under both batch and continuous flow conditions.

AB - Electron donor-acceptor (D-A) systems based on the benzo[c][1,2,5]thiadiazole (BTZ) motif have been extensively researched for use in photovoltaics or as fluorescent sensors. However, their use as potential visible-light organophotocatalysts has not received any in-depth study. Here we report the synthesis, characterisation, and application of a library of 26 D-A compounds based on the BTZ group. By varying the donor groups whilst keeping the BTZ acceptor group the same, we have been able to systematically modify the photocatalyst's optoelectronic and photophysical properties. These photocatalysts were then validated using a Minisci-type decarboxylative alkylation of electron deficient heteroarenes as a test reaction under both batch and continuous flow conditions.

UR - http://www.scopus.com/inward/record.url?scp=85138057148&partnerID=8YFLogxK

U2 - 10.1039/D2QO01316A

DO - 10.1039/D2QO01316A

M3 - Article

SN - 2052-4129

VL - 9

SP - 5473

EP - 5484

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 20

ER -

4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

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