Controlling association kinetics in the formation of donor-acceptor pseudorotaxanes

Paul R. McGonigal, Hao Li, Chuyang Cheng, Severin T. Schneebeli, Marco Frasconi, Leah S. Witus, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Abstract We report a systematic investigation of size-complementary stoppering groups used to determine the kinetics of threading a cyclophane, namely cyclobis(paraquat-p-phenylene), onto a series of molecular dumbbells. We have identified a set of simple functionalized phenyl and biaryl groups that present activation energy barriers between 16.7 and 26.6 kcal mol-1 to threading the dumbbells. These barriers will be employed as 'steric speed bumps' to modulate kinetics in artificial molecular pumps that operate based upon a delicate balance of noncovalent bonding interactions.

Original languageEnglish
Article number45839
Pages (from-to)3591-3594
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
Publication statusPublished - 25 May 2015

Bibliographical note

Funding Information:
This material is based on work supported by the National Science Foundation (NSF) under CHE-1308107. P.R.M. thanks the US–UK Fulbright Commission for an All-Disciplines Scholarship. S.T.S. and L.S.W. acknowledge support from the International Institute for Nanotechnology (IIN) at Northwestern University .

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

  • Cyclophane
  • Inclusion complex
  • Kinetics
  • Pseudorotaxane

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