Self-assembly of a [2]Pseudorota[3]catenane in water

Ross S. Forgan; Jeremiah J. Gassensmith; David B. Cordes; Megan M. Boyle; Karel J. Hartlieb; Douglas C. Friedman; Alexandra M.Z. Slawin; J. Fraser Stoddart

doi:10.1021/ja3085115

Self-assembly of a [2]Pseudorota[3]catenane in water

Ross S. Forgan, Jeremiah J. Gassensmith, David B. Cordes, Megan M. Boyle, Karel J. Hartlieb, Douglas C. Friedman, Alexandra M.Z. Slawin, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

37 Scopus citations

Abstract

A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p- phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H⋯O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.

Original language	English (US)
Pages (from-to)	17007-17010
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	41
DOIs	https://doi.org/10.1021/ja3085115
State	Published - Oct 17 2012

ASJC Scopus subject areas

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja3085115

Cite this

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title = "Self-assembly of a [2]Pseudorota[3]catenane in water",

abstract = "A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p- phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H⋯O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.",

author = "Forgan, {Ross S.} and Gassensmith, {Jeremiah J.} and Cordes, {David B.} and Boyle, {Megan M.} and Hartlieb, {Karel J.} and Friedman, {Douglas C.} and Slawin, {Alexandra M.Z.} and Stoddart, {J. Fraser}",

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language = "English (US)",

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journal = "Journal of the American Chemical Society",

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T1 - Self-assembly of a [2]Pseudorota[3]catenane in water

AU - Forgan, Ross S.

AU - Gassensmith, Jeremiah J.

AU - Cordes, David B.

AU - Boyle, Megan M.

AU - Hartlieb, Karel J.

AU - Friedman, Douglas C.

AU - Slawin, Alexandra M.Z.

AU - Stoddart, J. Fraser

PY - 2012/10/17

Y1 - 2012/10/17

N2 - A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p- phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H⋯O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.

AB - A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p- phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H⋯O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.

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Self-assembly of a [2]Pseudorota[3]catenane in water

Abstract

ASJC Scopus subject areas

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CCDC 898084: Experimental Crystal Structure Determination

CCDC 898081: Experimental Crystal Structure Determination

CCDC 898080: Experimental Crystal Structure Determination

Cite this

Self-assembly of a [2]Pseudorota[3]catenane in water

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 898084: Experimental Crystal Structure Determination

CCDC 898081: Experimental Crystal Structure Determination

CCDC 898080: Experimental Crystal Structure Determination

Cite this