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 languageEnglish
Pages (from-to)29102-29107
JournalRSC Advances
Volume11
Issue number47
Early online date1 Sep 2021
DOIs
Publication statusPublished - 2021

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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