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Liquid-Crystalline Bisadducts of [60]Fullerene
Auteur(s)
Campidelli, Stéphane
Editeur(s)
Vázquez, Ester
Milic, Dragana
Lenoble, Julie
Atienza Castellanos, Carmen
Sarova, Ginka
Guldi, Dirk M.
Prato, Maurizio
Date de parution
2006
In
The Journal of Organic Chemistry (JOC), American Chemical Society (ACS), 2006/71/20/7603–7610
Résumé
A second-generation cyanobiphenyl-based dendrimer was used as a liquid-crystalline promoter to synthesize mesomorphic bisadducts of [60]fullerene. Liquid-crystalline <i>trans</i>-2, <i>trans</i>-3, and equatorial bisadducts were obtained by condensation of the liquid-crystalline promoter, which carries a carboxylic acid function, with the corresponding bisaminofullerene derivatives. A monoadduct of fullerene was also prepared for comparative purposes. All the compounds gave rise to smectic A phases. An additional mesophase, which could not be identified, was observed for the <i>trans</i>-2 derivative. The supramolecular organization of the monoadduct derivative is governed by steric constraints. Indeed, for efficient space filling, adequacy between the cross-sectional areas of fullerene (∼100 Å<sup>2</sup>) and of the mesogenic groups (∼22−25 Å<sup>2</sup> per mesogenic group) is required. As a consequence, the monoadduct forms a bilayered smectic A phase. The supramolecular organization of the bisadducts is essentially governed by the nature and structure of the mesogenic groups and dendritic core. Therefore, the bisadducts form monolayered smectic A phases. The title compounds are promising supramolecular materials as they combine the self-organizing behavior of liquid crystals with the properties of fullerene.
Autre version
http://dx.doi.org/10.1021/jo0609576
Type de publication
Resource Types::text::journal::journal article
