4.8 Article

Reversible and Selective Encapsulation of Dextromethorphan and β-Estradiol Using an Asymmetric Molecular Capsule Assembled via the Weak-Link Approach

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 4, Pages 1368-1371

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b10027

Keywords

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Funding

  1. National Science Foundation [CHE-1149314]
  2. Department of Defense National Security Science and Engineering [N00014-15-1-0043]
  3. U.S. Army [W911NF-15-1-0151]
  4. Consejo Nacional de Ciencia y Tecnologia (CONACYT)
  5. National Defense Science and Engineering Graduate Fellowship
  6. National Science Foundation Graduate Research Fellowship

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An allosterically regulated, asymmetric receptor featuring a binding cavity large enough to accommodate three-dimensional pharmaceutical guest molecules as opposed to planar, rigid aromatics, was synthesized via the Weak-Link Approach. This architecture is capable of switching between an expanded, flexible open configuration and a collapsed, rigid closed one. The structure of the molecular receptor can be completely modulated in situ through the use of simple ionic effectors, winch reversibly control the coordination state of the Pt(II) metal hinges to open and close the molecular receptor. The substantial change in binding cavity size and electrostatic charge between the two configurations is used to explore the capture and release of two guest molecules, dextromethorphan and beta-estradiol, which are widely found as pollutants in groundwater.

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