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.
Highlights
Photoluminescent materials such as organic dyes and uorescent polymers have multiple applications in areas such as chemical sensing, organic electronics and bioimaging.[1]
While other mechanistic pathways exist, such as the twisted intramolecular charge transfer process (TICT)[6] or crystallisation-induced emission enhancement (CIEE),[7] the aforementioned restriction of intramolecular motion (RIM) process is dominant for most AIEgen materials.[4]
Quinolone 2 was reacted with 2-chloroarylboronic acids or pinacol esters in a two-step, C–C and C–N bond forming process to afford the desired deazacanthin-4-ones 3.21 quinolone 2 was reacted with 4,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan2-yl)benzo[c][1,2,5]thiadiazole [BTZ(Bpin)2] (4) to give the desired 8,80-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4
Summary
Photoluminescent materials such as organic dyes and uorescent polymers have multiple applications in areas such as chemical sensing, organic electronics and bioimaging.[1].
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