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Synthesis and Study of New β-Cyclodextrin ‘Dimers’ Having a Metal Coordination Center and carboxamide or urea linkers

✍ Scribed by Florence Sallas; Alain Marsura; Virginie Petot; István Pintér; Joseph Kovács; Laszlo Jicsinszky

Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
912 KB
Volume
81
Category
Article
ISSN
0018-019X

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✦ Synopsis

The synthesis of new 'bridged' p-cyclodextrin (p-CD) 'dimers' 7-12 was successfully achieved by two one-pot reactions from p-CD (3) and 6A-azido-6A-deoxy-p-CD (4). The 'phosphine imine' reaction was shown to be a superior approach compared to the Mitsunobu reaction as coupling strategy for the preparation of these 'dimers'. NMR Data, along with molecular-modelling calculations, suggest a 'helical-like' arrangement for the phenanthroline-diyl-linked 'dimer' derivative 9. Complexation properties of 9 were established by UV-VIS-spectrophotometric titration toward four metals. Among them Cu" or Eu"' ions were complexed selectively by 9, but no complexation occurred with La"' and Zn". In addition a specific and interesing esterase activity toward the phosphodiester bond of bis(4-nitrophenyl) phosphate anion was found in the case of the Cu" complex of 9.

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