Work

Acyclic cucurbit[ n ]uril bearing alkyl sulfate ionic groups

Year: 2025

Type: article

Abstract: We report the synthesis and characterization of a new acyclic cucurbit[ n ]uril (CB[ n ]) host C1 that features four alkyl sulfate ionic groups. The X-ray crystal structure of the C1·Me 6 CHDA complex is reported. Host C1 is significantly less soluble in water (4 mM) compared to the analogous acyclic CB[ n ] host M1 which features sulfonate ionic groups (346 mM). Host C1 does not undergo significant self-association according to the results of 1 H NMR dilution experiments. The molecular recognition behavior of the hosts C1 and M1 toward a panel of seven ammonium ions was explored by 1 H NMR spectroscopy and isothermal titration calorimetry (ITC). We find that C1 generally binds slightly more tightly than M1 toward a specific guest. C1 binds more tightly to quaternary ammonium guests compared to the corresponding primary ammonium ions.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.55

Authors: Christian Akakpo, Peter Y Zavalij, Lyle Isaacs

Institution: University of Maryland, College Park

Language: English

Topic: Supramolecular Chemistry and Complexes

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, National Institute of General Medical Sciences

Awards: Synthesis and Recognition Properties of Cucurbit[n]uril Type Receptors, G2683173438, Cucurbit[n]uril-Type Molecular Containers