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Article: Constitutionally asymmetric and chiral [2]pseudorotaxanes
Title | Constitutionally asymmetric and chiral [2]pseudorotaxanes |
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Authors | |
Issue Date | 1998 |
Citation | Journal of the American Chemical Society, 1998, v. 120, n. 5, p. 920-931 How to Cite? |
Abstract | The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a π-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by 1H NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. In particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings - the chirality present in the π-electron rich threadlike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the π-donors in the chiral guests but also the π-acceptors in the achiral host. |
Persistent Identifier | http://hdl.handle.net/10722/332437 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
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 | Hayes, Wayne | - |
dc.contributor.author | Janssen, Henk M. | - |
dc.contributor.author | Meijer, E. W. | - |
dc.contributor.author | Menzer, Stephan | - |
dc.contributor.author | Pasini, Dario | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.contributor.author | White, Andrew J.P. | - |
dc.contributor.author | Williams, David J. | - |
dc.date.accessioned | 2023-10-06T05:11:28Z | - |
dc.date.available | 2023-10-06T05:11:28Z | - |
dc.date.issued | 1998 | - |
dc.identifier.citation | Journal of the American Chemical Society, 1998, v. 120, n. 5, p. 920-931 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332437 | - |
dc.description.abstract | The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a π-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by 1H NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. In particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings - the chirality present in the π-electron rich threadlike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the π-donors in the chiral guests but also the π-acceptors in the achiral host. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Constitutionally asymmetric and chiral [2]pseudorotaxanes | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja970018i | - |
dc.identifier.scopus | eid_2-s2.0-0032506944 | - |
dc.identifier.volume | 120 | - |
dc.identifier.issue | 5 | - |
dc.identifier.spage | 920 | - |
dc.identifier.epage | 931 | - |
dc.identifier.isi | WOS:000072002600009 | - |