TUTCRIS - Tampereen teknillinen yliopisto

TUTCRIS

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

Tutkimustuotosvertaisarvioitu

Yksityiskohdat

AlkuperäiskieliEnglanti
Sivut5884-5894
Sivumäärä11
JulkaisuJournal of Organic Chemistry
Vuosikerta85
Numero9
DOI - pysyväislinkit
TilaJulkaistu - 2020
OKM-julkaisutyyppiA1 Alkuperäisartikkeli

Tiivistelmä

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.

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