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- Publisher Website: 10.1002/chem.200304798
- Scopus: eid_2-s2.0-0142074879
- PMID: 14566866
- WOS: WOS:000185933100005
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Article: In the twilight zone between [2]pseudorotaxanes and [2]rotaxanes
Title | In the twilight zone between [2]pseudorotaxanes and [2]rotaxanes |
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Authors | |
Keywords | Electrochemistry Kinetics Rotaxanes Self-assembly Supramolecular chemistry |
Issue Date | 2003 |
Citation | Chemistry - A European Journal, 2003, v. 9, n. 19, p. 4611-4625 How to Cite? |
Abstract | A [2]pseudorotaxane, based on a semi-dumbbell-shaped component containing asymmetrically substituted monopyrrolotetrathiafulvalene and 1,5-dioxynaphthalene recognition sites for encirclement by cyclobis(paraquat-p-phenylene) and with a "speed bump" in the form of a thiomethyl group situated between the two recognition sites, has been self-assembled. This supramolecular entity is a mixture in solution of two slowly interconverting [2]pseudorotaxanes, one of which is on the verge of being a [2]rotaxane at room temperature, allowing it to be isolated by employing flash column chromatography. These two [2]pseudorotaxanes were both characterized in solution by UV/Vis and 1H NMR spectroscopies (1D and 2D) and also by differential pulse voltammetry. The spectroscopic and electrochemical data reveal that one of the complexes behaves wholly as a [2]pseudorotaxane, while the other has some [2]rotaxane character to it. The kinetics of the shuttling of cyclobis(paraquat-p-phenylene) between the monopyrrolotetrathiafulvalene and the 1,5-dioxynaphthalene recognition sites have been investigated at different temperatures. The shuttling processes, which are accompanied by detectable color changes, can be monitored using UV/ Vis and 1H NMR spectroscopies; the spectroscopic data have been employed in the determination of the rate constants, free energies of activation, enthalpies of activation, and the entropies of activation for the translation of cyclobis(paraquat-p-phenylene) between the two recognition sites. |
Persistent Identifier | http://hdl.handle.net/10722/332546 |
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 | Jeppesen, Jan O. | - |
dc.contributor.author | Vignon, Scott A. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:12:21Z | - |
dc.date.available | 2023-10-06T05:12:21Z | - |
dc.date.issued | 2003 | - |
dc.identifier.citation | Chemistry - A European Journal, 2003, v. 9, n. 19, p. 4611-4625 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332546 | - |
dc.description.abstract | A [2]pseudorotaxane, based on a semi-dumbbell-shaped component containing asymmetrically substituted monopyrrolotetrathiafulvalene and 1,5-dioxynaphthalene recognition sites for encirclement by cyclobis(paraquat-p-phenylene) and with a "speed bump" in the form of a thiomethyl group situated between the two recognition sites, has been self-assembled. This supramolecular entity is a mixture in solution of two slowly interconverting [2]pseudorotaxanes, one of which is on the verge of being a [2]rotaxane at room temperature, allowing it to be isolated by employing flash column chromatography. These two [2]pseudorotaxanes were both characterized in solution by UV/Vis and 1H NMR spectroscopies (1D and 2D) and also by differential pulse voltammetry. The spectroscopic and electrochemical data reveal that one of the complexes behaves wholly as a [2]pseudorotaxane, while the other has some [2]rotaxane character to it. The kinetics of the shuttling of cyclobis(paraquat-p-phenylene) between the monopyrrolotetrathiafulvalene and the 1,5-dioxynaphthalene recognition sites have been investigated at different temperatures. The shuttling processes, which are accompanied by detectable color changes, can be monitored using UV/ Vis and 1H NMR spectroscopies; the spectroscopic data have been employed in the determination of the rate constants, free energies of activation, enthalpies of activation, and the entropies of activation for the translation of cyclobis(paraquat-p-phenylene) between the two recognition sites. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | Electrochemistry | - |
dc.subject | Kinetics | - |
dc.subject | Rotaxanes | - |
dc.subject | Self-assembly | - |
dc.subject | Supramolecular chemistry | - |
dc.title | In the twilight zone between [2]pseudorotaxanes and [2]rotaxanes | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/chem.200304798 | - |
dc.identifier.pmid | 14566866 | - |
dc.identifier.scopus | eid_2-s2.0-0142074879 | - |
dc.identifier.volume | 9 | - |
dc.identifier.issue | 19 | - |
dc.identifier.spage | 4611 | - |
dc.identifier.epage | 4625 | - |
dc.identifier.isi | WOS:000185933100005 | - |