Citation: Xuanyu Wang, Zhao Gao, Wei Tian. Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction[J]. Chinese Chemical Letters, ;2024, 35(11): 109757. doi: 10.1016/j.cclet.2024.109757 shu

Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction

Xuanyu Wang ¹ ,
Zhao Gao ^1,*, ,
Wei Tian ^*,

Shaanxi Key Laboratory of Macromolecular Science and Technology, Xi'an Key Laboratory of Hybrid Luminescent Materials and Photonic Device, MOE Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an 710072, China

gaozhao@nwpu.edu.cn

happytw_3000@nwpu.edu.cn

Received Date: 3 January 2024
Revised Date: 27 February 2024
Accepted Date: 8 March 2024
Available Online: 16 March 2024

Figures(3)

The supramolecular Förster resonance energy transfer (FRET) is seen as a promising approach for organic photocatalysis using dyes as catalysts, because it combines the high efficiency of energy transfer with the dynamic responsiveness based on non-covalent interactions. Here we propose a supramolecular FRET photocatalysis strategy for α-oxyamination reaction based on supramolecular confinement effect. The well-designed benzothiadiazole-based cationic monomer as energy donor and the dyes of Nile Red as acceptor are doped into the amphiphilic surfactants of sodium dodecyl sulfate (SDS). Benefitting from the supramolecular confinement space provided by SDS in aqueous environment, the FRET process between the monomer and Nile Red is effectively achieved (exciton migration rate: 3.99 × 10¹⁴ L mol^‒1 s^‒1). On this basis, the supramolecular FRET system is used as an efficient energy source to catalyze α-oxyamination reactions between a series of 1,3-dicarbonyl compounds and 2,2,6,6-tetramethylpiperidine-1-oxyl under white LED light, showing a yield as high as 94% and a turnover frequency value of 3.92 h^‒1. This photocatalytic result shows a great enhancement compared to that of Nile Red alone.
- Self-assembly,
- Supramolecular chemistry,
- Light harvesting,
- Energy transfer,
- Confinement effect
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