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Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

Zhihang Bai, K. Velmurugan, Xueqi Tian, Minzan Zuo, Kaiya Wang, Xiao‐Yu Hu

2022Beilstein Journal of Organic Chemistry22 citationsDOIOpen Access PDF

Abstract

Herein, we have designed and fabricated a simple and efficient supramolecular self-assembled nanosystem based on host–guest interactions between water-soluble tetraphenylethylene-embedded pillar[5]arene ( m -TPEWP5 ) and ammonium benzoyl-ʟ-alaninate ( G ) in an aqueous medium. The obtained assembly of m -TPEWP5 and G showed aggregation-induced emission (AIE) via the blocking of intramolecular phenyl-ring rotations and functioned as an ideal donor. After the loading of eosin Y ( EsY ) as acceptor on the surface of the assembly of m -TPEWP5 and G , the worm-like nanostructures changed into nanorods, which facilitates a Förster resonance energy transfer (FRET) from the m -TPEWP5 and G assembled donor to the EsY acceptor present in the nanorod assembly. The system comprising m -TPEWP5 , G and EsY displayed moderate FRET efficiency (31%) at a 2:1 molar ratio of donor-to-acceptor. Moreover, the obtained supramolecular nanorod assembly could act as a nanoreactor mimicking natural photosynthesis and exhibited a high catalytic efficiency for the photocatalytic dehalogenation reaction of various bromoketone derivatives with good yields in short reaction time in water.

Topics & Concepts

ChemistryPhotocatalysisTetraphenylethylenePillarSelf-assemblyNanotechnologyCombinatorial chemistryAggregation-induced emissionOrganic chemistryCatalysisMaterials scienceQuantum mechanicsPhysicsStructural engineeringFluorescenceEngineeringLuminescence and Fluorescent MaterialsSupramolecular Self-Assembly in MaterialsSupramolecular Chemistry and Complexes
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