Rotaxane formation by cucurbit[7]uril in water and DMSO solutions

Sanem Senler, Beijun Cheng, Angel E. Kaifer

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

The cucurbit[7]uril (CB7) host forms rotaxane-type complexes with dumbbell-shaped, cationic guests bis(3,5-dimethoxybenzyl)-4,4′-bipyridinium (12+) and bis(3,5-diethoxybenzyl)-4,4′-bipyridinium (22+). The kinetics of complex formation is slower with the latter guest because of its bulkier end groups. Rotaxane formation was found to be thermodynamically more favorable and kinetically faster in D2O than in DMSO-d6 solution, which highlights the importance of hydrophobic interactions in the assembly of cucurbituril complexes.

Original languageEnglish (US)
Pages (from-to)5834-5837
Number of pages4
JournalOrganic letters
Volume16
Issue number22
DOIs
StatePublished - Nov 21 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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