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

Department of Chemistry

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

16 Citations (Scopus)

35 Downloads (CityUHK Scholars)

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
Journal	Organic Chemistry Frontiers
Volume	9
Issue number	20
Online published	19 Aug 2022
DOIs	https://doi.org/10.1039/d2qo01316a
Publication status	Published - 21 Oct 2022

Research Keywords

BENZOTHIADIAZOLE DERIVATIVES
PHOTOREDOX CATALYSIS
SMALL MOLECULES
ALKYLATION
DYES
BENZOSELENADIAZOLE
FUNCTIONALIZATION
PHOTOCATALYSTS
HETEROARENES
TECHNOLOGY

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This full text is made available under CC-BY 4.0. https://creativecommons.org/licenses/by/4.0/

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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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.",

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doi = "10.1039/d2qo01316a",

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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

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

Abstract

Research Keywords

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