4.8 Article

Naphthocage: A Flexible yet Extremely Strong Binder for Singly Charged Organic Cations

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 10, Pages 4468-4473

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b00445

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Funding

  1. National Natural Science Foundation of China [21572097, 21822104, 21801125]
  2. Shenzhen Special Funds [KQJSCX20170728162528382, JCYJ20170307105848463]
  3. Shenzhen Nobel Prize Scientists Laboratory Project [C17213101]
  4. China Scholarship Council (CSC)
  5. Deutsche Forschungsgemeinschaft [CRC 765]

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We report a quite flexible naphthol-based cage (so-called naphthocage) which adopts a self-inclusion conformation in its free state and is able to bind singly charged organic cations extremely strongly (K-a > 10(7) M-1). Ion-selective electrodes prepared with this naphthocage show a super-Nernstian response to acetylcholine. In addition, the highly stable complex (10(10) M-1) between ferrocenium and the naphthocage can be switched electrochemically, which lays a basis for its application in stimuli-responsive materials.

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