Designing liquid-crystalline dendronised hexa-adducts of [60]fullerene via click chemistry |
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| Authors: | Julien Iehl Thi Le Anh Nguyen Stéphane Frein Uwe Hahn Joaquín Barberá Jean-François Nierengarten |
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| Institution: | 1. Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, Strasbourg, France;2. Institut de Chimie, Université de Neuchatel, Neuchatel, Switzerland;3. Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Arágon, Universidad de Zaragoza-CSIC, Zaragoza, Spain |
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| Abstract: | 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. |
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| Keywords: | Hexa-adducts of fullerene cyanobiphenyl-based dendrimers click chemistry liquid crystals smectic phases columnar rectangular phases |
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