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

RSC Adv. 2021 Sep 1;11(47):29102-29107. doi: 10.1039/d1ra06263h.

Authors

Emmanouil Broumidis¹, Callum M S Jones², Maria Koyioni³, Andreas Kourtellaris³, Gareth O Lloyd⁴, Jose Marques-Hueso², Panayiotis A Koutentis³, Filipe Vilela¹

Affiliations

¹ Institute of Chemical Sciences, School of Engineering & Physical Sciences, Heriot-Watt University Edinburgh EH14 4AS UK F.Vilela@hw.ac.uk.
² Institute of Sensors, Signals and Systems, School of Engineering & Physical Sciences, Heriot-Watt University Edinburgh EH14 4AS UK.
³ Department of Chemistry, University of Cyprus P.O. Box 20537 1678 Nicosia Cyprus.
⁴ Joseph Banks Laboratories, School of Chemistry, University of Lincoln Brayford Pool Lincoln LN6 7TS 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.