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- Publisher Website: 10.1039/c4sc00488d
- Scopus: eid_2-s2.0-84901856668
- WOS: WOS:000337108200015
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Article: An ExBox [2]catenane
Title | An ExBox [2]catenane |
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Authors | |
Issue Date | 2014 |
Citation | Chemical Science, 2014, v. 5, n. 7, p. 2724-2731 How to Cite? |
Abstract | A donor-acceptor [2]catenane, in which an extended tetracationic cyclophane is mechanically interlocked by a porphyrin-containing macrocycle, was synthesised using a template-directed protocol and alkene metathesis as the ring-closing step. In the ground state of this [2]catenane, the porphyrin ring resides inside the cavity of the cyclophane on account of favourable charge-transfer interactions between the electron-rich porphyrin and the electron-deficient cyclophane. The [2]catenane can act as a push-button molecular switch where the co-conformations of the [2]catenane can be controlled either chemically or electrochemically. Addition of acid protonates the porphyrin ring and a relative circumrotational motion of the macrocycle positions the charged porphyrin ring outside the cavity of the cyclophane. The switch can be reset to its ground-state co-conformation by the addition of base. Electrochemical reduction of the extended bipyridinium units of the cyclophane decreases the strength of the donor-acceptor interactions in the [2]catenane, leading to a loss of recognition between the mechanically interlocked rings. The chemical and electrochemical switching mechanisms are both reversible. © 2014 the Partner Organisations. |
Persistent Identifier | http://hdl.handle.net/10722/333076 |
ISSN | 2023 Impact Factor: 7.6 2023 SCImago Journal Rankings: 2.333 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Juríček, Michal | - |
dc.contributor.author | Barnes, Jonathan C. | - |
dc.contributor.author | Strutt, Nathan L. | - |
dc.contributor.author | Vermeulen, Nicolaas A. | - |
dc.contributor.author | Ghooray, Kala C. | - |
dc.contributor.author | Dale, Edward J. | - |
dc.contributor.author | McGonigal, Paul R. | - |
dc.contributor.author | Blackburn, Anthea K. | - |
dc.contributor.author | Avestro, Alyssa Jennifer | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:16:33Z | - |
dc.date.available | 2023-10-06T05:16:33Z | - |
dc.date.issued | 2014 | - |
dc.identifier.citation | Chemical Science, 2014, v. 5, n. 7, p. 2724-2731 | - |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.uri | http://hdl.handle.net/10722/333076 | - |
dc.description.abstract | A donor-acceptor [2]catenane, in which an extended tetracationic cyclophane is mechanically interlocked by a porphyrin-containing macrocycle, was synthesised using a template-directed protocol and alkene metathesis as the ring-closing step. In the ground state of this [2]catenane, the porphyrin ring resides inside the cavity of the cyclophane on account of favourable charge-transfer interactions between the electron-rich porphyrin and the electron-deficient cyclophane. The [2]catenane can act as a push-button molecular switch where the co-conformations of the [2]catenane can be controlled either chemically or electrochemically. Addition of acid protonates the porphyrin ring and a relative circumrotational motion of the macrocycle positions the charged porphyrin ring outside the cavity of the cyclophane. The switch can be reset to its ground-state co-conformation by the addition of base. Electrochemical reduction of the extended bipyridinium units of the cyclophane decreases the strength of the donor-acceptor interactions in the [2]catenane, leading to a loss of recognition between the mechanically interlocked rings. The chemical and electrochemical switching mechanisms are both reversible. © 2014 the Partner Organisations. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemical Science | - |
dc.title | An ExBox [2]catenane | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/c4sc00488d | - |
dc.identifier.scopus | eid_2-s2.0-84901856668 | - |
dc.identifier.volume | 5 | - |
dc.identifier.issue | 7 | - |
dc.identifier.spage | 2724 | - |
dc.identifier.epage | 2731 | - |
dc.identifier.eissn | 2041-6539 | - |
dc.identifier.isi | WOS:000337108200015 | - |