Integrating replication processes with mechanically interlocked molecular architectures

Annick Vidonne, Douglas Philp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

A kinetic model for the integration of self-replication with the formation of a mechanically interlocked molecular architecture, namely a rotaxane, is presented. The logical steps required to convert this model into molecular structures through consideration of the design criteria highlighted by the model are discussed and executed. Ultimately, despite careful design, the rotaxane synthesised did not replicate as expected. The reasons for this failure are traced by experiment and computation to the sub-optimal association constant for the pseudorotaxane complex required to form the replicating rotaxane. Additionally, a deleterious supramolecular steric effect, operating through the proximity of the macrocyclic component of the pseudorotaxane to the transition state for the stoppering reaction is identified computationally.

Original languageEnglish (US)
Pages (from-to)8464-8475
Number of pages12
JournalTetrahedron
Volume64
Issue number36
DOIs
StatePublished - Sep 1 2008

Keywords

  • Kinetics
  • Molecular recognition
  • Rotaxanes
  • Self-replication

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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