Self-assembled [2]catenanes exhibiting highly selective translational isomerism

David B. Amabilino; Peter R. Ashton; George R. Brown; Wayne Hayes; J. Fraser Stoddart; Malcolm S. Tolley; David J. Williams

doi:10.1039/C39940002479

Self-assembled [2]catenanes exhibiting highly selective translational isomerism

David B. Amabilino^*, Peter R. Ashton, George R. Brown, Wayne Hayes, J. Fraser Stoddart, Malcolm S. Tolley, David J. Williams

^*Corresponding author for this work

Chemistry

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

14 Scopus citations

Abstract

Template-directed synthesis is used to construct two isomeric [2]catenanes incorporating the macrocyclic polyether, (paraphenylene-metaphenylene)-33-crown- 10, and either (i) cyclobis (paraquat-p-phenylene) or (ii) cyclo(paraquat-p- phenylene)(paraquat-m-phenylene) as their tetrakis(hexafluorophosphates); these isomeric [2]catenanes are found to have a remarkable preference to exist as one translational isomer, both in the solid (by X-ray crystallography) and solution (by variable-temperature ¹H NMR spectroscopy) states-the one in which a hydrouinone, rather than a resorcinol, ring is located inside the cavities of the isomeric tetracationic cyclophanes.

Original language	English (US)
Pages (from-to)	2479-2482
Number of pages	4
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/C39940002479
State	Published - 1994

ASJC Scopus subject areas

Molecular Medicine

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title = "Self-assembled [2]catenanes exhibiting highly selective translational isomerism",

abstract = "Template-directed synthesis is used to construct two isomeric [2]catenanes incorporating the macrocyclic polyether, (paraphenylene-metaphenylene)-33-crown- 10, and either (i) cyclobis (paraquat-p-phenylene) or (ii) cyclo(paraquat-p- phenylene)(paraquat-m-phenylene) as their tetrakis(hexafluorophosphates); these isomeric [2]catenanes are found to have a remarkable preference to exist as one translational isomer, both in the solid (by X-ray crystallography) and solution (by variable-temperature 1H NMR spectroscopy) states-the one in which a hydrouinone, rather than a resorcinol, ring is located inside the cavities of the isomeric tetracationic cyclophanes.",

author = "Amabilino, {David B.} and Ashton, {Peter R.} and Brown, {George R.} and Wayne Hayes and Stoddart, {J. Fraser} and Tolley, {Malcolm S.} and Williams, {David J.}",

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doi = "10.1039/C39940002479",

language = "English (US)",

pages = "2479--2482",

journal = "Journal of the Chemical Society, Chemical Communications",

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publisher = "Chemical Society",

number = "21",

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T1 - Self-assembled [2]catenanes exhibiting highly selective translational isomerism

AU - Amabilino, David B.

AU - Ashton, Peter R.

AU - Brown, George R.

AU - Hayes, Wayne

AU - Stoddart, J. Fraser

AU - Tolley, Malcolm S.

AU - Williams, David J.

PY - 1994

Y1 - 1994

N2 - Template-directed synthesis is used to construct two isomeric [2]catenanes incorporating the macrocyclic polyether, (paraphenylene-metaphenylene)-33-crown- 10, and either (i) cyclobis (paraquat-p-phenylene) or (ii) cyclo(paraquat-p- phenylene)(paraquat-m-phenylene) as their tetrakis(hexafluorophosphates); these isomeric [2]catenanes are found to have a remarkable preference to exist as one translational isomer, both in the solid (by X-ray crystallography) and solution (by variable-temperature 1H NMR spectroscopy) states-the one in which a hydrouinone, rather than a resorcinol, ring is located inside the cavities of the isomeric tetracationic cyclophanes.

AB - Template-directed synthesis is used to construct two isomeric [2]catenanes incorporating the macrocyclic polyether, (paraphenylene-metaphenylene)-33-crown- 10, and either (i) cyclobis (paraquat-p-phenylene) or (ii) cyclo(paraquat-p- phenylene)(paraquat-m-phenylene) as their tetrakis(hexafluorophosphates); these isomeric [2]catenanes are found to have a remarkable preference to exist as one translational isomer, both in the solid (by X-ray crystallography) and solution (by variable-temperature 1H NMR spectroscopy) states-the one in which a hydrouinone, rather than a resorcinol, ring is located inside the cavities of the isomeric tetracationic cyclophanes.

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Self-assembled [2]catenanes exhibiting highly selective translational isomerism

Abstract

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