Source:http://linkedlifedata.com/resource/pubmed/id/17330312
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
14
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pubmed:dateCreated |
2007-5-24
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pubmed:abstractText |
Chirality can hold the key to inducing directionality of motion in components of molecular devices. With this idea in mind, we describe here 1) the template-directed synthesis of two [2]catenanes wherein cyclobis(paraquat-p-phenylene) is interlocked with polyether macrocycles containing, in addition to one 3,5-bis(oxymethylene)-1H-1,2,4-triazole unit, either one 1,4-dioxybenzene or one 1,5-dioxynaphthalene ring system. We also report 2) the full characterization of both [2]catenanes by fast atom bombardment mass spectrometry (FABMS), X-ray crystallography, and dynamic (1)H NMR spectroscopy. We reveal 3) the fact that the [2]catenanes not only exist, both in the solution-state and in the solid-state, as strictly one of the two possible translational isomers, but that they also exhibit spontaneous resolution on crystallization leading to formation of homochiral crystals, as indicated by X-ray crystallography and circular dichroism (CD) experiments. Finally, we comment 4) on the chances of switching these catenanes chemically.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:issn |
0947-6539
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
13
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
3964-79
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pubmed:dateRevised |
2009-8-4
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pubmed:meshHeading |
pubmed-meshheading:17330312-Circular Dichroism,
pubmed-meshheading:17330312-Crystallography, X-Ray,
pubmed-meshheading:17330312-Magnetic Resonance Spectroscopy,
pubmed-meshheading:17330312-Models, Molecular,
pubmed-meshheading:17330312-Protons,
pubmed-meshheading:17330312-Spectrometry, Mass, Electrospray Ionization,
pubmed-meshheading:17330312-Spectrometry, Mass, Fast Atom Bombardment,
pubmed-meshheading:17330312-Triazoles
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pubmed:year |
2007
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pubmed:articleTitle |
Nondegenerate pi-donor/pi-acceptor [2]catenanes containing proton-ionizable 1H-1,2,4-triazole subunits: synthesis and spontaneous resolution.
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pubmed:affiliation |
Laboratori de Química Orgànica, Facultat de Farmàcia and Institut de Nanociència i Nanotecnologia, Universitat de Barcelona, Avda. Joan XXIII s/n, 08028-Barcelona, Spain.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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