Bringing a Molecular plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes

Document Type

Article

Publication Date

5-1-2020

Publication Title

Journal of Organic Chemistry

Volume

85

Issue

9

First Page

5884

Last Page

5894

Abstract

Cethyl-2-methylresorcinarene (A), pyridine (B), and a set of 10 carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple noncovalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution, as explored by both experimental and computational methods. The interactions between A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions between A and B, demonstrating positive cooperativity. Our results reveal that the two-component system such as that formed by A and B can form the basis for the development of specific sensors for the molecular recognition of carboxylic acids.

DOI

10.1021/acs.joc.0c00220

ISSN

00223263

E-ISSN

15206904

PubMed ID

32174116

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