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A Redox-Active Heterocyclic Capsule: Radical Generation, Oxygenation, and Guest Uptake/Release

  • Yoshiyuki Satoh
    Yoshiyuki Satoh
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    More by Yoshiyuki Satoh
  • , 
  • Lorenzo Catti
    Lorenzo Catti
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    More by Lorenzo Catti
    Orcidhttp://orcid.org/0000-0003-0727-0620
  • , 
  • Munetaka Akita
    Munetaka Akita
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    More by Munetaka Akita
    Orcidhttp://orcid.org/0000-0001-7007-9621
  • , and 
  • Michito Yoshizawa*
    Michito Yoshizawa
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    *E-mail: [email protected]
    More by Michito Yoshizawa
    Orcidhttp://orcid.org/0000-0002-0543-3943
Cite this: J. Am. Chem. Soc. 2019, 141, 31, 12268–12273
Publication Date (Web):July 9, 2019
https://doi.org/10.1021/jacs.9b03419
Copyright © 2019 American Chemical Society
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    Abstract

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    For the development of a redox-active supramolecular capsule with host function, we synthesized a bent heterocyclic amphiphile using phenothiazine panels capable of adopting three different states, i.e., neutral, radical, and oxygenated states. In water, the new amphiphiles spontaneously and quantitatively assemble into a heterocycle-based capsule with an average diameter of ∼2 nm, through the hydrophobic effect and π-stacking interactions. The product structure was confirmed by the combination of NMR, UV–visible, DLS, AFM, and molecular modeling studies. Electrochemical and chemical oxidation of the capsule generates relatively stable radical cation capsules at room temperature in a reversible fashion. The neutral capsule efficiently takes up large hydrophobic compounds (e.g., pigment blue 15 and fullerene C60) into the heterocyclic cavity through a grinding protocol and subsequent chemical oxidation of the products generates radical host–guest complexes. Moreover, chemical oxygenation of the host–guest complexes was shown to induce guest release in water via disassembly of the capsular structure through dioxygenation of the phenothiazine panels.

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