4.6 Article

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

Journal

RSC ADVANCES
Volume 11, Issue 47, Pages 29102-29107

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ra06263h

Keywords

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Funding

  1. CRITICAT Centre for Doctoral Training [EP/L016419/1]
  2. Engineering and Physical Sciences Research Council [EP/T013680/1]
  3. EPSRC [EP/T013680/1] Funding Source: UKRI

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A new benzothiadiazole (BTZ) luminogen was prepared via Suzuki-Miyaura Pd-catalysed C-C cross-coupling, showing excellent AIE properties and stability under various conditions. It also acts as a molecular heterogeneous photosensitizer for singlet oxygen production in continuous flow.
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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