Journal article

Authors list: King, D; Sumanovac, T; Murkli, S; Schreiner, PR; Sekutor, M; Isaacs, L

Publication year: 2023

Pages: 5338-5346

Journal: New Journal of Chemistry

Volume number: 47

Issue number: 11

ISSN: 1144-0546

eISSN: 1369-9261

Open access status: Hybrid

DOI Link: https://doi.org/10.1039/d3nj00156c

Publisher: Royal Society of Chemistry

Abstract: 
We report the synthesis of quaternary (di)cationic triamantane derivatives G1 and G3 by the permethylation of the corresponding primary ammonium ions G2 and G4. The complexation behaviors of G1-G4 toward CB[7] and CB[8] were examined by H-1 NMR spectroscopy, which reveals that CB[8] is capable of fully encapsulating G1-G4 whereas CB[7] forms inclusion complexes with G1, G2, and G4 but cannot fully encapsulate the central hydrophobic core of the bis-quaternary ammonium ion G3. The geometries of the CB[n]-guest complexes were determined by analyzing the complexation induced changes in chemical shifts and were further confirmed by molecular modelling using the Conformer-Rotamer Ensemble Sampling Tool (CREST) based on the GFN methods. Finally, the complexation thermodynamics were determined by a combination of H-1 NMR competitive experiments, direct isothermal titration calorimetry (ITC) measurements, and competitive ITC titrations using a tight binding ternary complex as a competitor.

Harvard Citation style: King, D., Sumanovac, T., Murkli, S., Schreiner, P., Sekutor, M. and Isaacs, L. (2023) Cucurbit[8]uril forms tight inclusion complexes with cationic triamantanes, New Journal of Chemistry, 47(11), pp. 5338-5346. https://doi.org/10.1039/d3nj00156c

APA Citation style: King, D., Sumanovac, T., Murkli, S., Schreiner, P., Sekutor, M., & Isaacs, L. (2023). Cucurbit[8]uril forms tight inclusion complexes with cationic triamantanes. New Journal of Chemistry. 47(11), 5338-5346. https://doi.org/10.1039/d3nj00156c