8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties

Emmanouil Broumidis; Callum Jones; Maria Koyioni; Andreas Kourtellaris; Gareth O. Lloyd; Jose Marques-Hueso; Panayiotis A. Koutentis; Filipe Vilela

doi:10.1039/d1ra06263h

8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties

Emmanouil Broumidis, Callum Jones, Maria Koyioni, Andreas Kourtellaris, Gareth O. Lloyd, Jose Marques-Hueso, Panayiotis A. Koutentis, Filipe Vilela

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Abstract

A new benzothiadiazole (BTZ) luminogen is prepared via the Suzuki–Miyaura Pd-catalysed C–C cross-coupling of 8-iodoquinolin-4(1H)-one and a BTZ bispinacol boronic ester. The rapid reaction (5 min) affords the air-, thermo-, and photostable product in 97% yield as a yellow precipitate that can be isolated by filtration. The luminogen exhibits aggregated-induced emission (AIE) properties, which are attributed to its photoactive BTZ core and nonplanar geometry. It also behaves as a molecular heterogeneous photosensitizer for the production of singlet oxygen under continuous flow conditions.

Original language	English
Pages (from-to)	29102-29107
Journal	RSC Advances
Volume	11
Issue number	47
Early online date	1 Sept 2021
DOIs	https://doi.org/10.1039/d1ra06263h
Publication status	Published - 2021

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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title = "8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties",

abstract = "A new benzothiadiazole (BTZ) luminogen is prepared via the Suzuki–Miyaura Pd-catalysed C–C cross-coupling of 8-iodoquinolin-4(1H)-one and a BTZ bispinacol boronic ester. The rapid reaction (5 min) affords the air-, thermo-, and photostable product in 97% yield as a yellow precipitate that can be isolated by filtration. The luminogen exhibits aggregated-induced emission (AIE) properties, which are attributed to its photoactive BTZ core and nonplanar geometry. It also behaves as a molecular heterogeneous photosensitizer for the production of singlet oxygen under continuous flow conditions.",

author = "Emmanouil Broumidis and Callum Jones and Maria Koyioni and Andreas Kourtellaris and Lloyd, {Gareth O.} and Jose Marques-Hueso and Koutentis, {Panayiotis A.} and Filipe Vilela",

note = "Funding Information: E. B. would like to thank the CRITICAT Centre for Doctoral Training (EP/L016419/1) for funding. C. J and J. M-H would like to thank the Engineering and Physical Sciences Research Council (EP/T013680/1) for funding. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

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language = "English",

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AU - Broumidis, Emmanouil

AU - Jones, Callum

AU - Koyioni, Maria

AU - Kourtellaris, Andreas

AU - Lloyd, Gareth O.

AU - Marques-Hueso, Jose

AU - Koutentis, Panayiotis A.

AU - Vilela, Filipe

N1 - Funding Information: E. B. would like to thank the CRITICAT Centre for Doctoral Training (EP/L016419/1) for funding. C. J and J. M-H would like to thank the Engineering and Physical Sciences Research Council (EP/T013680/1) for funding. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021

Y1 - 2021

N2 - A new benzothiadiazole (BTZ) luminogen is prepared via the Suzuki–Miyaura Pd-catalysed C–C cross-coupling of 8-iodoquinolin-4(1H)-one and a BTZ bispinacol boronic ester. The rapid reaction (5 min) affords the air-, thermo-, and photostable product in 97% yield as a yellow precipitate that can be isolated by filtration. The luminogen exhibits aggregated-induced emission (AIE) properties, which are attributed to its photoactive BTZ core and nonplanar geometry. It also behaves as a molecular heterogeneous photosensitizer for the production of singlet oxygen under continuous flow conditions.

AB - A new benzothiadiazole (BTZ) luminogen is prepared via the Suzuki–Miyaura Pd-catalysed C–C cross-coupling of 8-iodoquinolin-4(1H)-one and a BTZ bispinacol boronic ester. The rapid reaction (5 min) affords the air-, thermo-, and photostable product in 97% yield as a yellow precipitate that can be isolated by filtration. The luminogen exhibits aggregated-induced emission (AIE) properties, which are attributed to its photoactive BTZ core and nonplanar geometry. It also behaves as a molecular heterogeneous photosensitizer for the production of singlet oxygen under continuous flow conditions.

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DO - 10.1039/d1ra06263h

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JO - RSC Advances

JF - RSC Advances

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ER -

8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties

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