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

• Published in: Journal of the American Chemical Society Vol. 139; no. 4; pp. 1368 - 1371
• Main Authors: Mendez-Arroyo, Jose, d’Aquino, Andrea I, Chinen, Alyssa B, Manraj, Yashin D, Mirkin, Chad A
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.02.2017
• Subjects: Coordination Complexes - chemical synthesis; Coordination Complexes - chemistry; Dextromethorphan - chemistry; Estradiol - chemistry; Molecular Structure; Platinum - chemistry; Quantum Theory; Static Electricity
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/jacs.6b10027

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, which 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 β-estradiol, which are widely found as pollutants in groundwater.