Issue 21, 2018

Intramolecularly enhanced molecular tweezers with unusually strong binding for aromatic guests in unfavorable solvents

Abstract

Molecular tweezers using aromatic interactions for binding normally work best in polar instead of nonpolar solvents due to the strong solvophobic effect in the binding. Inspired by biological receptors that utilize “delocalized binding interactions” remote from the binding interface to strengthen guest-binding, we constructed molecular tweezers that have a reversed solvent effect. As the direct aromatic binding interactions were weakened by nonpolar solvent, guest-triggered intrahost interactions between two strategically placed carboxylic acids became stronger and contributed to the binding.

Graphical abstract: Intramolecularly enhanced molecular tweezers with unusually strong binding for aromatic guests in unfavorable solvents

Supplementary files

Article information

Article type
Communication
Submitted
03 Apr. 2018
Accepted
07 Maijs 2018
First published
07 Maijs 2018

Org. Biomol. Chem., 2018,16, 3885-3888

Author version available

Intramolecularly enhanced molecular tweezers with unusually strong binding for aromatic guests in unfavorable solvents

X. Xing and Y. Zhao, Org. Biomol. Chem., 2018, 16, 3885 DOI: 10.1039/C8OB00786A

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