期刊
ACS CATALYSIS
卷 8, 期 12, 页码 11277-11286出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b02502
关键词
copper photosensitizer; bis(arylimino)acenaphthene; transient absorption spectroscopy; time-correlated single photon counting; visible-light photoredox catalysis; carbon-carbon bond formation
资金
- MOE Tier 1 grants [M4011611, M4011791]
- Agency for Science, Technology and Research (A*STAR)
- AME IRG [A1783c0002, A1783c0003, A1783c0007]
- Solar Fuels Lab at NTU
- MOE Tier 1 grant [RG115/16]
Currently, the most popular molecular photo sensitizers used for synthetic organic chemistry and energy applications are still the noble-metal-based ruthenium and iridium complexes that usually require expensive metal and ligand precursors. In contrast, bis(arylimino)acenaphthene (Ar-BIAN) is an established redox noninnocent pi-accepting ligand that is easily assembled in one condensation step from affordable and commercially available precursors. Herein, we have developed a series of Ar-BIAN Cu-I complexes as visible light-harvesting photosensitizers. Notably, one of these panchromatic, homoleptic Ar-BIAN Cu-I complexes exhibits a radiative recombination lifetime that is longer than diffusion controlled reactions, as observed by time-correlated single photon counting spectroscopy. Ar-BIAN Cu-I facilitates visible-light-promoted carbon-carbon bond formation with CBr3 radicals in good yields of up to 75%. Steady-state and transient absorption spectroscopic measurements, together with spectroelectrochemical experiments and intermediate isolation studies, were performed to obtain insights into this photoredox catalysis and provide guidelines for the general deployment of Ar-BIAN Cu-I photosensitizers in synthetic organic chemistry and renewable energy applications.
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