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A Donor–Acceptor [2]Catenane for Visible Light Photocatalysis

  • Yang Jiao
    Yang Jiao
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    More by Yang Jiao
  • Luka Đorđević
    Luka Đorđević
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Center for Bio-inspired Energy Science, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  • Haochuan Mao
    Haochuan Mao
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Institute for Sustainability and Energy at Northwestern, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    More by Haochuan Mao
  • Ryan M. Young
    Ryan M. Young
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Institute for Sustainability and Energy at Northwestern, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  • Tyler Jaynes
    Tyler Jaynes
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Center for Bio-inspired Energy Science, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    More by Tyler Jaynes
  • Hongliang Chen
    Hongliang Chen
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  • Yunyan Qiu
    Yunyan Qiu
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    More by Yunyan Qiu
  • Kang Cai
    Kang Cai
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    More by Kang Cai
  • Long Zhang
    Long Zhang
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    More by Long Zhang
  • Xiao-Yang Chen
    Xiao-Yang Chen
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  • Yuanning Feng
    Yuanning Feng
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  • Michael R. Wasielewski
    Michael R. Wasielewski
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Institute for Sustainability and Energy at Northwestern, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  • Samuel I. Stupp*
    Samuel I. Stupp
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Center for Bio-inspired Energy Science, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Department of Materials Science and Engineering, Northwestern University, 2220 Campus Drive, Evanston, Illinois 60208, United States
    Department of Biomedical Engineering, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    Department of Medicine, Northwestern University, 676 North St. Clair Street, Chicago, Illinois 60611, United States
    Simpson Querrey Institute, Northwestern University, Chicago, Illinois 60611, United States
    *[email protected]
  • , and 
  • J. Fraser Stoddart*
    J. Fraser Stoddart
    Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
    School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia
    Department of Chemistry, Zhejiang University, Hangzhou 310027, China
    *[email protected]
Cite this: J. Am. Chem. Soc. 2021, 143, 21, 8000–8010
Publication Date (Web):May 24, 2021
https://doi.org/10.1021/jacs.1c01493
Copyright © 2021 American Chemical Society

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    Abstract

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    Colored charge-transfer complexes can be formed by the association between electron-rich donor and electron-deficient acceptor molecules, bringing about the narrowing of HOMO–LUMO energy gaps so that they become capable of harnessing visible light. In an effort to facilitate the use of these widespread, but nonetheless weak, interactions for visible light photocatalysis, it is important to render the interactions strong and robust. Herein, we employ a well-known donor–acceptor [2]catenane—formed by the mechanical interlocking of cyclobis(paraquat-p-phenylene) and 1,5-dinaphtho[38]crown-10—in which the charge-transfer interactions between two 4,4′-bipyridinium and two 1,5-dioxynaphthalene units are enhanced by mechanical bonding, leading to increased absorption of visible light, even at low concentrations in solution. As a result, since this [2]catenane can generate persistent bipyridinium radical cations under continuous visible-light irradiation without the need for additional photosensitizers, it can display good catalytic activity in both photo-reductions and -oxidations, as demonstrated by hydrogen production—in the presence of platinum nanoparticles—and aerobic oxidation of organic sulfides, such as l-methionine, respectively. This research, which highlights the usefulness of nanoconfinement present in mechanically interlocked molecules for the reinforcement of weak interactions, can not only expand the potential of charge-transfer interactions in solar energy conversion and synthetic photocatalysis but also open up new possibilities for the development of active artificial molecular shuttles, switches, and machines.

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    • Detailed synthetic procedures and supplemental characterization data (NMR, EPR, and UV/vis absorption spectra, and electrochemical measurements as well as GC and HPLC traces) (PDF)

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