Folding of a donor-acceptor polyrotaxane by using noncovalent bonding interactions

Wenyu Zhang, William R. Dichtel, Adam Z. Stieg, Diego Benítez, James K. Gimzewski, James R. Heath, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

67 Scopus citations

Abstract

Mechanically interlocked compounds, such as bistable catenanes and bistable rotaxanes, have been used to bring about actuation in nanoelectromechanical systems (NEMS) and molecular electronic devices (MEDs). The elaboration of the structural features of such rotaxanes into macromolecular materials might allow the utilization of molecular motion to impact their bulk properties. We report here the synthesis and characterization of polymers that contain π electron-donating 1,5-dioxynaphthalene (DNP) units encircled by cyclobis(paraquat-p-phenylene) (CBPQT4+), a π electron-accepting tetracationic cyclophane, synthesized by using the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The polyrotaxanes adopt a well defined "folded" secondary structure by virtue of the judicious design of two DNP-containing monomers with different binding affinities for CBPQT 4+. This efficient approach to the preparation of polyrotaxanes, taken alongside the initial investigations of their chemical properties, sets the stage for the preparation of a previously undescribed class of macromolecular architectures.

Original languageEnglish (US)
Pages (from-to)6514-6519
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume105
Issue number18
DOIs
StatePublished - May 6 2008

Keywords

  • Click chemistry
  • Foldamers
  • Polymers
  • Rotaxanes
  • Supramolecular chemistry

ASJC Scopus subject areas

  • General

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