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  • 1
    Electronic Resource
    Electronic Resource
    Nanometre-scale molecular ribbonsDedicated to Professor Heinz A. Staab on the occasion of his 70th birthday (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 832-837 
    Details
    ISSN: 0947-6539
    Keywords: cyclophanes ; macrocyclisations ; molecular ribbons ; nanostructures ; repetitive syntheses ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The longest molecular ribbons known to date (3-10), composed of a series of [3.3]metacyclophane units, have been synthesised by means of a repetitive synthetic strategy. These multiple ring systems with up to nine bridged benzene rings in a row are the longest structurally perfect cyclophane sequences known to date. The synthetic strategy comprises three steps: ester reduction to a tetrakis(hydroxymethyl) compound, derivatisation to the corresponding tetrakis(bromomethyl) derivative, and double cyclisation with the new key building block 14, which was especially developed for this sequence. Single-crystal X-ray analyses (3 a-7 a) and 1H NMR spectroscopy (3-10) show that, regardless of their length, these molecules adopt zigzag folded all-syn conformations. π-Stacks of nanometre dimensions are thus formed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.1460020714
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  • 2
    Electronic Resource
    Electronic Resource
    Molecular Ribbons Containing Pyridine Rings (1996)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1996 (1996), S. 2115-2121 
    Details
    ISSN: 0947-3440
    Keywords: Cyclophanes ; Macrocycles ; Phanes ; Pyridinophanes ; Ring compounds ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of the ribbon-like compounds 6-10 is described. The new building block diethyl 2,6-bis(bromomethyl)pyridine-3,5-dicarboxylate 1 was prepared and characterized. Single-crystal X-ray structure analyses indicate that these ribbon-like molecules arrange in a folded conformation, with the pyridine and benzene units being folded in a face-to-face manner, and the tosyl units of 8-10 pointing outwards. The “intramolecular self-assembly” (folding) of these molecular ribbons is primarily attributable to the energetically more favourable syn conformation of both the [3.3]metacyclophanes and the pyridinophanes.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199619961225
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