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  • 1
    ISSN: 1573-1111
    Keywords: Crown ethers ; urea(-like) guests ; complexation ; crystal structures
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The preparation and X-ray structure determinations of six complexes of urea and (O-n-butyliso)uronium salts with crown ethers are presented. Urea forms isostructural 5:1 adducts with 18-crown-6 (1) and aza-18-crown-6 (2), in which two urea molecules are each hydrogen bonded to two neighbouring hetero atoms of the macroring. The remaining urea molecules form two-dimensional layers alternating with crown ether layers. In both complexes the macroring has theg + g + a ag − a ag − a g − g − a ag + a ag + a conformation withC i symmetry. In the solid 1:1 complex of O-n-butylisouronium picrate with 18-crown-6 (3) two types of conformations of the macroring were observed: theg + g + a ag − a ag + a ag − g − ag − a ag + a conformation with approximateC m symmetry and to a lesser extent theg + g + a ag − a ag + a g + g + a ag − a ag + a conformation with approximateC 2 symmetry. Both conformations allow the guest to form three hydrogen bonds to the macrocyclic host. Three complexes of 18-crown-6 and uronium salts have been prepared and characterized by X-ray crystallography. The 1:1 complexes with uronium nitrate (4) and uronium picrate (5) both exhibit the sameC 2 conformation and the same hydrogen bonding scheme as in the least occupied form of the previous complex. A 1:2 complex with uroniump-toluenesulphonate (6) has a different hydrogen bonding scheme (two hydrogen bonds per cation to neighbouring oxygen atoms of the macroring) and a different conformation of the host molecule (theag + a ag − a ag + a ag − a ag + a ag − a conformation with almostD 3d symmetry). An attempt to prepare a solid uronium nitrate complex with diaza-18-crown-6 in the same way as the 18-crown-6·uronium nitrate (1:1) complex did not yield the expected result. Instead X-ray analysis revealed that the uronium ion is dissociated, resulting in the nitrate salt of the diprotonated diaza crown ether (7).
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1434-193X
    Keywords: Calixarenes ; Chromophores ; Nonlinear optics ; Pre-organization ; Supramolecular chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A systematic investigation of the conceptofpre-organization of nonlinear optical (NLO) active chromophoric groups in calix[4]arene derivatives and the influence on the absolute second-order nonlinear optical coefficients is reported. Several calix[4]arenes were synthesized by modification of the electron-withdrawing groups at the upper rim of the aromatic and extension of the conjugated π system of the pre-organized chromophoric groups. Electrical field induced second harmonic generation (EFISH) experiments showed high μβ(0) values up to 1165·10-48 esu. Compared with the corresponding reference compounds, enhancements of the μβ(0) values varying up to 2.5 times per chromophore were observed which proves the benefit of pre-organization of NLO-active units in a multi-chromophoric system. Another important advantage is that the increase in NLO activity observed for these systems is not accompanied with a shift of the absorption band to longer wavelengths exceeding 20 nm. This makes these calix[4]arene derivatives promising building blocks for the development of stable, NLO-active materials that are suitable for frequency doubling.
    Type of Medium: Electronic Resource
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