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  • 1
    Electronic Resource
    Electronic Resource
    Syntheses of Donor-Acceptor-Substituted 2,6-Stellanes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 73-81 
    Details
    ISSN: 1434-193X
    Keywords: Donor-acceptor systems ; Cage compounds ; Stelladione ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A number of condensations could be carried out using tricyclo[3.3.0.03,7]octane-2-one (stellanone, 4) and tricyclo[3.3.0.03,7]octane-2,6-dione (2,6-stelladione, 5) as starting materials. The components for condensations were 2-trimethylsilyl-1,3-dithiane (6), 1,1-bis(trimethylsilyl)-1H-cyclopropa[b]naphthalene (7), its 3,6-dimethoxy-substituted analogue 8, fluorene (12), xanthene (13), diethyl malonate (14), and malononitrile (15). The condensation reactions with 5 yielded mono- and disubstituted products, among them were the donor-acceptor-substituted 2,6-stellanes 33-35. The structures of 18 (prepared from stellanone and fluorene), 19, 24, 27, 31 and 32 (synthesized by condensation of 2,6-stelladione and 2-trimethylsilyl-1,3-dithiane and malononitrile, respectively) were determined by X-ray crystallography.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    The Cubane Cage - A Sensitive Probe for Assessing Substituent Effects on a Four-Membered Ring, Part II (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1253-1257 
    Details
    ISSN: 1434-193X
    Keywords: Cage compounds ; Cubanes ; Donor-acceptor systems ; Solid-state structures ; Substituent effects ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The crystal structures of methyl 4-methoxycubane-1-carboxylate (1), 1-acetamido-4-fluorocubane (2), methyl 4-acetoxycubane-1-carboxylate (3), 1,4-difluorocubane (4), 1,4-dichlorocubane (5), and N,N-diisopropylcubane-1,4-dicarboxamide (6) have been investigated by means of X-ray diffraction analysis. Fluorine and chlorine substituents cause a shortening of the vicinal bonds, as is seen in the 4-halocubane-1-carboxylates. The cage bonds vicinal to the ester substituent, with a favorable orientation with regard to the π-acceptor influence of this group become longer than the CH-CH bonds. Furthermore, the influence on bond length with respect to the orientation of this group relative to bonds within the cubane skeleton has been investigated experimentally. The effect of the methoxy group has also been found to depend on the orientation. The cage bond antiperiplanar to the methyl group is shortened, while the cage bonds in gauche orientation to this group are lengthened. As seen in the case of the halogen-substituted derivatives, the bonds bearing the acetoxy substituent are shortened due to the σ-acceptor property of this group. Ab initio calculations on compounds 1, 2, 4, and 5 performed at the 6-31G* level confirm the experimental results.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Substituent Effects on Redox Properties and Photoinduced Electron Transfer in Isoxazolo-Fullerenes (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 455-465 
    Details
    ISSN: 1434-193X
    Keywords: Fullerenes ; Cycloadditions ; Donor-acceptor systems ; Cyclic voltammetry ; Photoinduced electron transfer ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The new C60 and C70 adducts 1b, 1d-1k, 1m, 6d, 7d, and 8d have been synthesized by [2+3] cycloadditions of the appropriate nitrile oxides. Variations in the distance and geometry of the donor and acceptor substituents are seen to have an influence on the redox behavior of the fullerene adducts in cyclic voltammetry experiments. The isoxazolo-fullerenes 1c, 1d, and 1i show shifts of about 30 mV or 40 mV to more negative values compared with the reference compound 1a. On the other hand, strong acceptor properties are detected in the case of compound 1e, which shows a positive shift of 30 mV relative to 1a. Moreover, time-resolved fluorescence spectroscopy has shown that upon excitation of the fullerene moiety in the polar solvent benzonitrile, an electron is transferred from the donor substituent to the first excited singlet state of the fullerene, thereby reducing the excited-state lifetime. Our data demonstrate that the electron-transfer rate in donor-substituted fullerenes can be controlled by the electron-donating property of the substituent as well as the electronic structure and/or length of the spacer used. The C70 regioisomers 6d, 7d, and 8d exhibit differences in their spectroscopic characteristics.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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