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Designing liquid-crystalline dendronised hexa-adducts of [60]fullerene via click chemistry

AuthorsIehl, Julien; Nguyen, Thi Le Anh; Frein, Stéphane; Hahn, Uwe; Barberá, Joaquín; Nierengarten, Jean-François; Deschenaux, Robert
KeywordsHexa-adducts of fullerene
Cyanobiphenyl-based dendrimers
Click chemistry
Liquid crystals
Smectic phases
Columnar rectangular phases
Issue Date2017
PublisherTaylor & Francis
CitationLiquid Crystals 44(12-13): 1852-1860 (2017)
AbstractLiquid-crystalline [60]fullerodendrimers were constructed via click chemistry based on the reaction between hexa-adducts of [60]fullerene (C60) bearing 12 azide groups and alkyne-terminated cyanobiphenyl dendrons of first- and second-generation. The structure of all the new compounds was confirmed by IR, UV, 1H and 13C NMR spectroscopies and mass spectrometry. The mesomorphic properties were studied by polarised optical microscopy, differential scanning calorimetry and small-angle X-ray scattering. The hexa-adduct of C60 functionalised with the first-generation dendrons gave rise to the formation of a smectic A phase and a rectangular columnar phase (c2mm symmetry) while the hexa-adduct of C60 decorated with the second-generation dendrons displayed only a rectangular columnar phase (c2mm symmetry). Our results show that the hexa-adduct of C60 is a unique synthetic platform for the design of fullerodendrimers and dendronised materials.
Publisher version (URL)https://doi.org/10.1080/02678292.2017.1336677
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