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- Publisher Website: 10.1002/chem.19970030518
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Article: Self-assembly of novel [2]catenanes and [2]pseudorotaxanes incorporating thiacrown ethers or their acyclic analogues
Title | Self-assembly of novel [2]catenanes and [2]pseudorotaxanes incorporating thiacrown ethers or their acyclic analogues |
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Authors | |
Keywords | catenanes molecular devices pseudorotaxanes self-assembly translational isomerism |
Issue Date | 1997 |
Citation | Chemistry - A European Journal, 1997, v. 3, n. 5, p. 772-787 How to Cite? |
Abstract | A series of π electron rich macrocyclic polythioethers and their acyclic analogues have been synthesized in good yields. The association constants for the complexation of the π electron deficient bis(hexafluorophosphate) bipyridinium-based salt, paraquat, by these macrocycles, as well as those for the complexation of corresponding acyclic compounds by the bipyridinium-based tetracationic cyclophane, cyclobis(paraquat -p-phenylene), are significantly lower than those observed in the case of the 'all-oxygen' analogues. Nonetheless, yields as high as 86% were recorded in the template-directed syntheses of [2]catenanes composed of cyclobis(paraquat-p-phenylene) and the macrocyclic polythioethers. Single-crystal X-ray crystallographic analyses of the [2]catenanes incorporating constitutionally unsymmetrical π electron rich macrocyclic polythioethers revealed that, in all cases, the dioxyaromatic units are located inside the cavity of the tetracationic cyclophane component in preference to the dithiaaromatic units. A similar selectivity was observed in solution by variable-temperature 1H NMR spectroscopy. However, inversion of the ratio between the two translational isomers of the two [2]catenanes bearing 1,5-dithianaphthalene, as one of their π electron rich ring systems, and either 1,4-dioxybenzene or 1,5-dioxynaphthalene, as the other, occurs upon increasing the temperature from -30 to +30 C. These [2]catenanes can be viewed as temperature-responsive molecular switches. |
Persistent Identifier | http://hdl.handle.net/10722/332603 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Asakawa, Masumi | - |
dc.contributor.author | Ashton, Peter R. | - |
dc.contributor.author | Dehaen, Wim | - |
dc.contributor.author | L'abbé, Gerrit | - |
dc.contributor.author | Menzer, Stephan | - |
dc.contributor.author | Nouwen, Jan | - |
dc.contributor.author | Raymo, Françisco M. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.contributor.author | Tolley, Malcolm S. | - |
dc.contributor.author | Toppet, Suzanne | - |
dc.contributor.author | White, Andrew J.P. | - |
dc.contributor.author | Williams, David J. | - |
dc.date.accessioned | 2023-10-06T05:12:47Z | - |
dc.date.available | 2023-10-06T05:12:47Z | - |
dc.date.issued | 1997 | - |
dc.identifier.citation | Chemistry - A European Journal, 1997, v. 3, n. 5, p. 772-787 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332603 | - |
dc.description.abstract | A series of π electron rich macrocyclic polythioethers and their acyclic analogues have been synthesized in good yields. The association constants for the complexation of the π electron deficient bis(hexafluorophosphate) bipyridinium-based salt, paraquat, by these macrocycles, as well as those for the complexation of corresponding acyclic compounds by the bipyridinium-based tetracationic cyclophane, cyclobis(paraquat -p-phenylene), are significantly lower than those observed in the case of the 'all-oxygen' analogues. Nonetheless, yields as high as 86% were recorded in the template-directed syntheses of [2]catenanes composed of cyclobis(paraquat-p-phenylene) and the macrocyclic polythioethers. Single-crystal X-ray crystallographic analyses of the [2]catenanes incorporating constitutionally unsymmetrical π electron rich macrocyclic polythioethers revealed that, in all cases, the dioxyaromatic units are located inside the cavity of the tetracationic cyclophane component in preference to the dithiaaromatic units. A similar selectivity was observed in solution by variable-temperature 1H NMR spectroscopy. However, inversion of the ratio between the two translational isomers of the two [2]catenanes bearing 1,5-dithianaphthalene, as one of their π electron rich ring systems, and either 1,4-dioxybenzene or 1,5-dioxynaphthalene, as the other, occurs upon increasing the temperature from -30 to +30 C. These [2]catenanes can be viewed as temperature-responsive molecular switches. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | catenanes | - |
dc.subject | molecular devices | - |
dc.subject | pseudorotaxanes | - |
dc.subject | self-assembly | - |
dc.subject | translational isomerism | - |
dc.title | Self-assembly of novel [2]catenanes and [2]pseudorotaxanes incorporating thiacrown ethers or their acyclic analogues | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/chem.19970030518 | - |
dc.identifier.scopus | eid_2-s2.0-18844478093 | - |
dc.identifier.volume | 3 | - |
dc.identifier.issue | 5 | - |
dc.identifier.spage | 772 | - |
dc.identifier.epage | 787 | - |
dc.identifier.isi | WOS:A1997XJ95900015 | - |