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

Ken Cham Fai Leung; Kwun Ngai Lau; Wing Yan Wong

doi:10.3390/ijms16048254

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

Ken Cham Fai Leung^*, Kwun Ngai Lau, Wing Yan Wong

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

3 Citations (Scopus)

Abstract

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]pseudorotaxaneDB24C8⊃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.

Original language	English
Pages (from-to)	8254-8265
Number of pages	12
Journal	International Journal of Molecular Sciences
Volume	16
Issue number	4
DOIs	https://doi.org/10.3390/ijms16048254
Publication status	Published - 13 Apr 2015

Scopus Subject Areas

Catalysis
Molecular Biology
Spectroscopy
Computer Science Applications
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

User-Defined Keywords

Crown ether
Dissociation
Rotaxane
Slippage
Thermodynamic synthesis

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10.3390/ijms16048254

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

abstract = "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]pseudorotaxaneDB24C8⊃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.",

keywords = "Crown ether, Dissociation, Rotaxane, Slippage, Thermodynamic synthesis",

author = "Leung, {Ken Cham Fai} and Lau, {Kwun Ngai} and Wong, {Wing Yan}",

note = "Publisher Copyright: {\textcopyright} 2015 by the authors; licensee MDPI, Basel, Switzerland.",

year = "2015",

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T1 - Revisiting the formation and tunable dissociation of a [2]pseudorotaxane formed by slippage approach

AU - Leung, Ken Cham Fai

AU - Lau, Kwun Ngai

AU - Wong, Wing Yan

PY - 2015/4/13

Y1 - 2015/4/13

N2 - 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]pseudorotaxaneDB24C8⊃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.

AB - 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]pseudorotaxaneDB24C8⊃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.

KW - Crown ether

KW - Dissociation

KW - Rotaxane

KW - Slippage

KW - Thermodynamic synthesis

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DO - 10.3390/ijms16048254

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SN - 1661-6596

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JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

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ER -

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

Abstract

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