α- and β-cyclodextrin [2]rotaxanes with (diethylenetriamine) platinum(II) stoppers

Victor X Jin, Donal H. Macartney, Erwin Buncel

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A series of dinuclear platinum(II) complexes, [(dien)Pt(NH 2(CH2)nNH2)Pt(dien)]Cl4 (dien = diethylenetriamine, n = 8, 9, 10, and 12) and their corresponding [2]rotaxanes with α-cyclodextrin (α-CD), [(dien)Pt{NH 2(CH2)nNH2-α-CD}Pt(dien)] Cl4, have been synthesized and characterized by 1H, 13C, and 195Pt NMR spectroscopy and electrospray mass spectrometry. The rotaxanes were prepared by reacting the {NH 2(CH2)nNH2-α-CD} pseudorotaxanes with [Pt(dien)]Cl, to stopper the included linear α,ω-diaminoalkane chains with the inert Pt(II) end groups. The kinetics of the self-assembly and dissociation of the β-CD rotaxane, [(dien)Pt{NH2(CH2)10NH2· β-CD}Pt(dien)]4+, were investigated by using 1H NMR and are indicative of a slippage mechanism, owing to the comparable sizes of the β-CD cavity and the [Pt(dien)]+ end group. A relatively weak inclusion of the end group in the β-CD cavity precedes a thermally promoted passage of the β-CD over the [Pt(dien)]+ end group onto the hydrophobic polymethylene chain of the bridging ligand of the thread.

Original languageEnglish (US)
Pages (from-to)2091-2097
Number of pages7
JournalCanadian Journal of Chemistry
Volume83
Issue number12
DOIs
StatePublished - Dec 1 2005
Externally publishedYes

Fingerprint

Rotaxanes
Cyclodextrins
Self assembly
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Platinum
Ligands
Nuclear magnetic resonance
Kinetics
(diethylenetriamine)-platinum(II)
diaquadiethylenediamineplatinum(II)

Keywords

  • Cyclodextrin
  • Platinum complexes
  • Pseudorotaxanes
  • Rotaxanes
  • Slippage mechanism

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

α- and β-cyclodextrin [2]rotaxanes with (diethylenetriamine) platinum(II) stoppers. / Jin, Victor X; Macartney, Donal H.; Buncel, Erwin.

In: Canadian Journal of Chemistry, Vol. 83, No. 12, 01.12.2005, p. 2091-2097.

Research output: Contribution to journalArticle

Jin, Victor X ; Macartney, Donal H. ; Buncel, Erwin. / α- and β-cyclodextrin [2]rotaxanes with (diethylenetriamine) platinum(II) stoppers. In: Canadian Journal of Chemistry. 2005 ; Vol. 83, No. 12. pp. 2091-2097.
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AB - A series of dinuclear platinum(II) complexes, [(dien)Pt(NH 2(CH2)nNH2)Pt(dien)]Cl4 (dien = diethylenetriamine, n = 8, 9, 10, and 12) and their corresponding [2]rotaxanes with α-cyclodextrin (α-CD), [(dien)Pt{NH 2(CH2)nNH2-α-CD}Pt(dien)] Cl4, have been synthesized and characterized by 1H, 13C, and 195Pt NMR spectroscopy and electrospray mass spectrometry. The rotaxanes were prepared by reacting the {NH 2(CH2)nNH2-α-CD} pseudorotaxanes with [Pt(dien)]Cl, to stopper the included linear α,ω-diaminoalkane chains with the inert Pt(II) end groups. The kinetics of the self-assembly and dissociation of the β-CD rotaxane, [(dien)Pt{NH2(CH2)10NH2· β-CD}Pt(dien)]4+, were investigated by using 1H NMR and are indicative of a slippage mechanism, owing to the comparable sizes of the β-CD cavity and the [Pt(dien)]+ end group. A relatively weak inclusion of the end group in the β-CD cavity precedes a thermally promoted passage of the β-CD over the [Pt(dien)]+ end group onto the hydrophobic polymethylene chain of the bridging ligand of the thread.

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