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 M. S. 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,

^a Callum M. S. Jones,

^b Maria Koyioni,^c Andreas Kourtellaris,^c Gareth O. Lloyd,

^d Jose Marques-Hueso,

^b Panayiotis A. Koutentis

*^c and Filipe Vilela

*^a

Author affiliations

* Corresponding authors

^a Institute of Chemical Sciences, School of Engineering & Physical Sciences, Heriot-Watt University, Edinburgh, UK
E-mail: F.Vilela@hw.ac.uk

^b Institute of Sensors, Signals and Systems, School of Engineering & Physical Sciences, Heriot-Watt University, Edinburgh, UK

^c Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus

^d Joseph Banks Laboratories, School of Chemistry, University of Lincoln, Brayford Pool, Lincoln, UK

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.

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DOI: https://doi.org/10.1039/D1RA06263H
Article type: Paper
Submitted: 18 Aug 2021
Accepted: 23 Aug 2021
First published: 01 Sep 2021
This article is Open Access

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RSC Adv., 2021,11, 29102-29107

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

E. Broumidis, C. M. S. Jones, M. Koyioni, A. Kourtellaris, G. O. Lloyd, J. Marques-Hueso, P. A. Koutentis and F. Vilela, RSC Adv., 2021, 11, 29102 DOI: 10.1039/D1RA06263H

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

Abstract

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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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