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  • Supramolecular chemistry  (5)
  • Wiley-Blackwell  (5)
  • American Institute of Physics (AIP)
  • De Gruyter
  • Springer
  • Wiley
  • 1995-1999  (5)
  • 1950-1954
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Keywords
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  • Wiley-Blackwell  (5)
  • American Institute of Physics (AIP)
  • De Gruyter
  • Springer
  • Wiley
Years
Year
  • 1
    Electronic Resource
    Electronic Resource
    Chemical Reactions in the Axle of Rotaxanes - Steric Hindrance by the Wheel (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1233-1238 
    Details
    ISSN: 1434-193X
    Keywords: Electrophilic additions ; Bromine addition to double bonds ; Hydrogenation of double bonds ; Rotaxanes ; Supramolecular chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Here we report on the possibility of using rotaxane wheels as noncovalent protecting groups which significantly decrease the activity of functional groups in the central part of the axle. The amide-linked rotaxanes 5aand 5b, each containing a C=C double bond in their axle, have been synthesised. The catalytic hydrogenation of these two rotaxanes proceeds slower than those of the corresponding free axle compounds 6a and 6b, indicating steric hindrance of the C=C double bond by the wheel of the rotaxane in each case. Nontheless, the rotaxane 9with an aliphatic (succinic acid) middle region in its axle can be prepared in this manner. Dehydrobromination of the axle in the rotaxane 15yields the rotaxane 16 with a C≡C triple bond located in the centre of the axle.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Rotaxanes with Chiral Stoppers and Complexation of Cations by Podand Axles with Sugar Terminal GroupsDedicated to Professor S. Hünig on the occasion of his 75th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 495-499 
    Details
    ISSN: 0947-3440
    Keywords: Ligand ; Metal complexation ; Podand ; Sugar stopper ; Supramolecular chemistry ; Rotaxanes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The new π-donor/π-acceptor type rotaxanes 15, 16 bearing chiral sugar units as blocking groups have been synthesized in 2% and 6% yield, starting from acetobromo glucose 10 and the podands 8 or 9, followed by the reaction of the resulting axles 11 and 12 with the dicationic bis(bipyridinio) wheel precursor 13 and the bis(bromomethyl) compound 14. The capability of the podands 11 and 12 and of the rotaxanes 15 and 16 to form podate-like complexes with metal salts was investigated by NMR; the effect of metal thiocyanate salt addition was monitored. Distinct changes of proton shifts that indicate complex formation were only observed between the free axles 11, 12 and the metal salts, whereas no major effects were found in case of the rotaxanes 15, 16. Glucose entities were chosen as stopper units in order to support metal complexation as terminal groups and to introduce a source of chirality into the molecules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970309
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  • 3
    Electronic Resource
    Electronic Resource
    Non-Ionic Template Synthesis of Amide-Linked Rotaxanes: Olefinic and Aliphatic Axle Building Blocks (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2269-2273 
    Details
    ISSN: 0947-3440
    Keywords: Association constant ; Mechanical bonding ; Molecular recognition ; Template synthesis ; Supramolecular chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of amide-linked rotaxanes with non-arene axle building blocks is reported. The threading synthesis of rotaxane 8 with olefinic fumaryl chloride proves that arene moieties are not necessary for non-ionic template syntheses. Mass spectroscopic evidence of a rotaxane bearing an aliphatic axle, derived from succinic acid, revealed that hydrogen bonding, rather than π,π interactions, is the predominant template binding force. 1H-NMR titration studies on the threading synthesis of these mechanically bonded molecules were carried out. The association constants measured suggest that the incorporation of the corresponding monoamide monochloride (cf. 7), rather than the incorporation of the diacid dichloride (cf. 5), plays the key role in these rotaxane syntheses. The X-ray structural analysis of a semi axle (14) reveals hydrogen bonding patterns characteristic of diamides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971114
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  • 4
    Electronic Resource
    Electronic Resource
    Chiral Amide Rotaxanes with Glucose Stoppers - Synthesis, Chiroptical Properties and Wheel-Axle Interactions (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2003-2007 
    Details
    ISSN: 1434-193X
    Keywords: Supramolecular chemistry ; Rotaxanes ; Mechanical bond ; Molecular recognition ; Chirality ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In this paper we report on amide rotaxanes with tetrabenzoylglucose stoppers. When acetyl groups are used instead of benzoyl groups, merely a pseudo-rotaxane 5 is obtained. The circular dichroism measurements of the rotaxanes 6a and 6b differ significantly from that one of the free axle 7. Similarly, the Cotton effects of the mixtures of achiral wheels 2a and 2b and chiral axle indicate intermolecular host-guest interactions, likewise. After an addition of a solution of NaOMe the wheel is slipping off immediately and quantitatively by hydrolysis, as the benzoylglucose stoppers decrease in size by hydrolysis.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Chiral Pyridinophanes as Hydrogen-Bonding Supramolecular Building Blocks (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1221-1225 
    Details
    ISSN: 0947-3440
    Keywords: Aggregations ; Circular dichroism ; Cyclophanes ; Molecular recognition ; Supramolecular chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hydrogen-donor and hydrogen-acceptor substituted chiral cyclophanes with a [2](1,3)benzeno[2](3,5)pyridinophane framework have been synthesized, enantiomerically separated, and analysed by circular dichroism (CD). X-ray structure determination and CD analyses show that these cyclophanes are able to act as hydrogen-bonding donor/acceptor building blocks for the design of chiral supramolecular aggregates with suitable complementary partners. Starting from the pyridinophane N-oxide 4, selective reactions lead to the new chiral pyridinophanes 5-7 in high yields. The X-ray structure analysis of the pyridinophane-2-carbonitrile 5 reveals a multilayered herringbone structure as it forms dimeric aggregates. The CD analysis of the host 7 with the complementary guest molecules melamine and cyanuric acid elucidates the formation of supramolecular complexes in solution.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970626
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