Mechanically interlaced and interlocked donor-acceptor foldamers

Carson J. Bruns, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter

15 Scopus citations


The emergence of a class of organic oligomers and polymers that lie at the intersection of the fields of mechanically interlocked molecules (MIMs) and synthetic foldamers is described in this review. These macromolecules are based on 4,40-bipyridinium (BIPY2+) and 1,5-dioxynaphthalene (DNP) recognition units incorporated into linear oligo- or polymeric chains (threads) and macrocycles (rings), where the threads fold their way through a series of rings in a serpentinelike fashion. The well-defined geometries of these polyelectrolytes are rendered by the [C-H . . . O] hydrogen bonding interactions that transpire between the polyether chains appended to DNP and the acidic protons of BIPY2+, as well as the π-π and donor-acceptor (D-A) charge transfer interactions that cause DNP and BIPY2+ units to pack into extended mixed stacks. The unique folding motif of these pseudorotaxanes and rotaxanes makes them attractive candidates for novel multiferroic and mechanically tunable materials.

Original languageEnglish (US)
Title of host publicationHierarchical Macromolecular Structures
Subtitle of host publication60 Years After The Staudinger Nobel Prize I
PublisherSpringer New York LLC
Number of pages24
ISBN (Print)9783319011363
StatePublished - 2013

Publication series

NameAdvances in Polymer Science
ISSN (Print)0065-3195


  • [C-H . . . O]•interactions Donor-acceptor Foldamers Mechanostereochemistry Polyelectrolytes Rotaxanes π-π interactions

ASJC Scopus subject areas

  • General Chemical Engineering
  • Organic Chemistry
  • Polymers and Plastics


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