Organogel formation by a cholesterol-stoppered bistable [2]rotaxane and its dumbbell precursor

Yan Li Zhao, Ivan Aprahamian, Ali Trabolsi, Natalia Erina, J. Fraser Stoddart

Research output: Contribution to journalArticle

Abstract

The switching properties, gelation behavior, and self-organization of a cholesterol-stoppered bistable [2]rotaxane containing a cyclobis(paraquat-p-phenylene) ring and tetrathiafulvalene/1,5-dioxynaphthalene recognition units situated in the rod portion of the dumbbell component have been investigated by electrochemical, spectroscopic, and microscopic means. The cyclobis(paraquat-p-phenylene) ring in the [2]rotaxane can be switched between the tetrathiafulvalene and 1,5-dioxynaphthalene recognition units by addressing the redox properties of the tetrathiafulvalene unit. The organogels can be prepared by dissolving the [2]rotaxane and its dumbbell precursor in a CH2Cl2/MeOH (3:2) mixed solvent and liquified by adding the oxidant Fe(ClO4)3. Direct evidence for the self-organization was obtained from AFM investigations which have shown that both of the [2]rotaxane and its dumbbell precursor form linear superstructures which we propose are helical in nature.

Original languageEnglish (US)
Pages (from-to)6348-6350
Number of pages3
JournalJournal of the American Chemical Society
Volume130
Issue number20
DOIs
StatePublished - May 21 2008

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Rotaxanes
Cholesterol
Paraquat
Gelation
Oxidants
Oxidation-Reduction
tetrathiafulvalene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Organogel formation by a cholesterol-stoppered bistable [2]rotaxane and its dumbbell precursor. / Zhao, Yan Li; Aprahamian, Ivan; Trabolsi, Ali; Erina, Natalia; Stoddart, J. Fraser.

In: Journal of the American Chemical Society, Vol. 130, No. 20, 21.05.2008, p. 6348-6350.

Research output: Contribution to journalArticle

Zhao, Yan Li ; Aprahamian, Ivan ; Trabolsi, Ali ; Erina, Natalia ; Stoddart, J. Fraser. / Organogel formation by a cholesterol-stoppered bistable [2]rotaxane and its dumbbell precursor. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 20. pp. 6348-6350.
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