A water-soluble pH-triggered molecular switch

Sergio Grunder; Psaras L. McGrier; Adam C. Whalley; Megan M. Boyle; Charlotte Stern; J Fraser Stoddart

doi:10.1021/ja409006y

A water-soluble pH-triggered molecular switch

Sergio Grunder, Psaras L. McGrier, Adam C. Whalley, Megan M. Boyle, Charlotte Stern, J Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

Abstract

A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and ¹H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.

Original language	English (US)
Pages (from-to)	17691-17694
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	47
DOIs	https://doi.org/10.1021/ja409006y
State	Published - Nov 27 2013

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja409006y

Cite this

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title = "A water-soluble pH-triggered molecular switch",

abstract = "A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and 1H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.",

author = "Sergio Grunder and McGrier, {Psaras L.} and Whalley, {Adam C.} and Boyle, {Megan M.} and Charlotte Stern and Stoddart, {J Fraser}",

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doi = "10.1021/ja409006y",

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volume = "135",

pages = "17691--17694",

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T1 - A water-soluble pH-triggered molecular switch

AU - Grunder, Sergio

AU - McGrier, Psaras L.

AU - Whalley, Adam C.

AU - Boyle, Megan M.

AU - Stern, Charlotte

AU - Stoddart, J Fraser

PY - 2013/11/27

Y1 - 2013/11/27

N2 - A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and 1H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.

AB - A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and 1H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.

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U2 - 10.1021/ja409006y

DO - 10.1021/ja409006y

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EP - 17694

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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A water-soluble pH-triggered molecular switch

Abstract

ASJC Scopus subject areas

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CCDC 956144: Experimental Crystal Structure Determination

CCDC 956145: Experimental Crystal Structure Determination

CCDC 956146: Experimental Crystal Structure Determination

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A water-soluble pH-triggered molecular switch

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 956144: Experimental Crystal Structure Determination

CCDC 956145: Experimental Crystal Structure Determination

CCDC 956146: Experimental Crystal Structure Determination

Cite this