Surrogate-stoppered [2]rotaxanes: A new route to larger interlocked architectures

Stuart J. Rowan, J. Fraser Stoddart

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A novel synthetic strategy for exchanging stoppers on rotaxanes, without them losing their integrity as interlocked molecules, is presented. The surrogate-stoppered [2] rotaxane contains one inert stopper and a triphenylphosphonium group attached to a benzylic position as a second reactive stopper in the dumbbell-shaped component which contains an ammonium (NH2+) ion recognition site, encircled by a crown ether (24C8 or 25C8) component. The strategy for exchanging stoppers relies upon the ability of a benzylic triphenyl-phosphonium function to undergo a Wittig reaction with a bulky aromatic aldehyde to form a 'stilbenoid' [2] rotaxane as a mixture of cis and trans isomers, without the occurrence of any dethreading of the crown ether ring component. The C=C double bonds can then be hydrogenated, using Adams' catalyst, to afford a new covalently modified [2]rotaxane with two inert stoppers. Utilizing this strategy, larger interlocked molecular structures including a two-stationed [2]rotaxane and a branched [4]rotaxane have been prepared. Furthermore, initial studies, aimed at using this methodology to gain access to poly[n]rotaxane architectures, are presented.

Original languageEnglish
Pages (from-to)777-787
Number of pages11
JournalPolymers for Advanced Technologies
Volume13
Issue number10-12
Publication statusPublished - 2002 Oct
Externally publishedYes

Fingerprint

Rotaxanes
Crown ethers
Aldehydes
Isomers
Molecular structure
Crown Ethers
Catalysts
Molecules
Ions
Ammonium Compounds

Keywords

  • Macrocycles
  • Oligomers
  • Polyrotaxanes
  • Supramolecular structure
  • Wittig reaction

ASJC Scopus subject areas

  • Polymers and Plastics

Cite this

Surrogate-stoppered [2]rotaxanes : A new route to larger interlocked architectures. / Rowan, Stuart J.; Stoddart, J. Fraser.

In: Polymers for Advanced Technologies, Vol. 13, No. 10-12, 10.2002, p. 777-787.

Research output: Contribution to journalArticle

Rowan, Stuart J. ; Stoddart, J. Fraser. / Surrogate-stoppered [2]rotaxanes : A new route to larger interlocked architectures. In: Polymers for Advanced Technologies. 2002 ; Vol. 13, No. 10-12. pp. 777-787.
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