Photocatalytic Conversion of Nitrobenzene to Aniline through Sequential Proton-Coupled One-Electron Transfers from a Cadmium Sulfide Quantum Dot

Jensen, Stephen C.; Bettis Homan, Stephanie; Weiss, Emily A.

doi:10.1021/jacs.5b11353

Title: Photocatalytic Conversion of Nitrobenzene to Aniline through Sequential Proton-Coupled One-Electron Transfers from a Cadmium Sulfide Quantum Dot

Journal Article · Tue Jan 19 00:00:00 EST 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b11353· OSTI ID:1387522

Jensen, Stephen C. ^[1]; Bettis Homan, Stephanie ^[1]; Weiss, Emily A. ^[1]

Northwestern Univ., Evanston, IL (United States)

This paper describes the use of cadmium sulfide quantum dots (CdS QDs) as visible-light photocatalysts for the reduction of nitrobenzene to aniline through six sequential photoinduced, proton-coupled electron transfers. At pH 3.6–4.3, the internal quantum yield of photons-to-reducing electrons is 37.1% over 54 h of illumination, with no apparent decrease in catalyst activity. Monitoring of the QD exciton by transient absorption reveals that, for each step in the catalytic cycle, the sacrificial reductant, 3-mercaptopropionic acid, scavenges the excitonic hole in ~5 ps to form QD^•–; electron transfer to nitrobenzene or the intermediates nitrosobenzene and phenylhydroxylamine then occurs on the nanosecond time scale. The rate constants for the single-electron transfer reactions are correlated with the driving forces for the corresponding proton-coupled electron transfers. This result suggests, but does not prove, that electron transfer, not proton transfer, is rate-limiting for these reactions. Furthermore, nuclear magnetic resonance analysis of the QD–molecule systems shows that the photoproduct aniline, left unprotonated, serves as a poison for the QD catalyst by adsorbing to its surface. Performing the reaction at an acidic pH not only encourages aniline to desorb but also increases the probability of protonated intermediates; the latter effect probably ensures that recruitment of protons is not rate-limiting.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); US Army Research Office (ARO); Northwestern International Institute for Nanotechnology (I.I.N.)

Grant/Contract Number:: SC0001059

OSTI ID:: 1387522

Journal Information:: Journal of the American Chemical Society, Vol. 138, Issue 5; Related Information: ANSER partners with Northwestern University (lead); Argonne National Laboratory; University of Chicago; University of Illinois, Urbana-Champaign; Yale University; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 131 works

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Challenges and Prospects of Photocatalytic Applications Utilizing Semiconductor Nanocrystals Moroz, Pavel; Boddy, Anthony; Zamkov, Mikhail Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00353	journal	August 2018
Selective Transfer Coupling of Nitrobenzene to Azoxybenzene on Rh Nanoparticle Catalyst Promoted by Photoexcited Hot Electrons Dai, Xinyan; Wei, Qilin; Duong, Thao ChemNanoMat, Vol. 5, Issue 8 https://doi.org/10.1002/cnma.201900182	journal	May 2019
Synthesis of tailor-made colloidal semiconductor heterostructures Enright, Michael J.; Cossairt, Brandi M. Chemical Communications, Vol. 54, Issue 52 https://doi.org/10.1039/c8cc03498b	journal	January 2018
Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis: Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis Guo, Xingwei; Okamoto, Yasunori; Schreier, Mirjam R. European Journal of Organic Chemistry, Vol. 2020, Issue 10 https://doi.org/10.1002/ejoc.201900777	journal	August 2019
RGO-ZnSe Photocatalyst towards Solar-Light-Assisted Degradation of Tetracycline Antibiotic Water Pollutant Das, Poulomi; Pan, Arvind; Chakraborty, Koushik ChemistrySelect, Vol. 3, Issue 36 https://doi.org/10.1002/slct.201801657	journal	September 2018
Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water Zhao, Lei-Min; Meng, Qing-Yuan; Fan, Xiang-Bing Angewandte Chemie, Vol. 129, Issue 11 https://doi.org/10.1002/ange.201700243	journal	February 2017
Proton-coupled multi-electron transfer and its relevance for artificial photosynthesis and photoredox catalysis Pannwitz, Andrea; Wenger, Oliver S. Royal Society of Chemistry https://doi.org/10.5451/unibas-ep72000	text	January 2019
Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis Guo, Xingwei; Okamoto, Yasunori; Schreier, Mirjam R. Wiley https://doi.org/10.5451/unibas-ep72319	text	January 2019
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Resolving the Core and the Surface of CdSe Quantum Dots and Nanoplatelets Using Dynamic Nuclear Polarization Enhanced PASS–PIETA NMR Spectroscopy Piveteau, Laura; Ong, Ta-Chung; Walder, Brennan J. ACS Central Science, Vol. 4, Issue 9 https://doi.org/10.1021/acscentsci.8b00196	journal	June 2018
In Situ Preparation of CoP@CdS and Its Catalytic Activity toward Controlling Nitro Reduction under Visible-Light Irradiation Xu, Yong; Chen, Yong; Fu, Wen-Fu ACS Omega, Vol. 3, Issue 2 https://doi.org/10.1021/acsomega.7b01592	journal	February 2018

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
catalysis (homogeneous)
catalysis (heterogeneous)
solar (photovoltaic)
solar (fuels)
photosynthesis (natural and artificial)
bio-inspired
hydrogen and fuel cells
electrodes - solar
defects
charge transport
spin dynamics
membrane
materials and chemistry by design
optics
synthesis (novel materials)
synthesis (self-assembly)
quantum dots
charge transfer
plastics
molecules
biopolymers