Revisiting the formation and tunable dissociation of a [2]pseudorotaxane formed by slippage approach

A new [2]pseudorotaxane DB24C8⊃1-H · PF6 with dibenzo[24]crown-8 (DB24C8) crown ether-dibenzylammonium (1-H · PF6) binding which was formed by slippage approach at different solvents and temperature, had been isolated and characterized by NMR spectroscopy and mass spectrometry. The [2]pseudorotaxane...

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Bibliographic Details
Published in:International journal of molecular sciences 2015-04, Vol.16 (4), p.8254-8265
Main Authors: Leung, Ken Cham-Fai, Lau, Kwun-Ngai, Wong, Wing-Yan
Format: Article
Language:English
Subjects:
Chemical compounds
Dimethyl Sulfoxide - chemistry
Ethylamines - chemistry
Magnetic Resonance Spectroscopy - methods
Mass Spectrometry - methods
Molecular structure
Rotaxanes - chemistry
Solvents - chemistry
Temperature
Thermodynamics
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Summary:A new [2]pseudorotaxane DB24C8⊃1-H · PF6 with dibenzo[24]crown-8 (DB24C8) crown ether-dibenzylammonium (1-H · PF6) binding which was formed by slippage approach at different solvents and temperature, had been isolated and characterized by NMR spectroscopy and mass spectrometry. The [2]pseudorotaxane DB24C8⊃1-H · PF6 was stable at room temperature. The dissociation rate of [2]pseudorotaxane DB24C8⊃1-H · PF6 could be tuned by using different stimuli such as triethylamine (TEA)/diisopropylethylamine (DIPEA) and dimethyl sulfoxide (DMSO). In particular, the dissociation of [2]pseudorotaxane DB24C8⊃1-H · PF6 by an excess of TEA/DIPEA base mixture possessed a long and sustained, complete dissociation over 60 days. Other stimuli by DMSO possessed a relatively fast dissociation over 24 h.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms16048254