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

Yang Jiao, Luka Đorđević, Haochuan Mao, Ryan M. Young, Tyler Jaynes, Hongliang Chen, Yunyan Qiu, Kang Cai, Long Zhang, Xiao Yang Chen, Yuanning Feng, Michael R. Wasielewski, Samuel I. Stupp*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)8000-8010
Number of pages11
JournalJournal of the American Chemical Society
Volume143
Issue number21
DOIs
StatePublished - Jun 2 2021

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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