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  4. Macrocyclic Effects in the Mesomorphic Properties of Liquid-Crystalline Pillar[5]- and Pillar[6]arenes
 
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Macrocyclic Effects in the Mesomorphic Properties of Liquid-Crystalline Pillar[5]- and Pillar[6]arenes

Auteur(s)
Nierengarten, Iwona
Editeur(s)
Guerra, Sebastiano 
Institut de chimie 
Holler, Michel
Karmazin-Brelot, Lydia
Barberá, Joaquín
Deschenaux, Robert 
Institut de chimie 
Nierengarten, Jean-François
In
European Journal of Organic Chemistry, Wiley, 2013/2013/18/3675-3684
Mots-clés
  • Nanostructures

  • Macrocycles

  • Liquid crystals

  • Structure elucidation...

  • Click chemistry

Résumé
Whereas the reaction of 1,4-bis(2-bromoethyloxy)benzene (4) with paraformaldehyde in the presence of BF<sub>3</sub>·Et<sub>2</sub>O afforded exclusively the cyclopentameric pillar[5]arene derivative (5), both cyclopenta- and cyclohexameric macrocycles 5 and 6 were obtained when the reaction of 4 with paraformaldehyde was performed at 45 °C in CHCl<sub>3</sub> with FeCl<sub>3</sub> as the catalyst. Treatment of compounds 4–6 with sodium azide provided the corresponding polyazides, to which a cyanobiphenyl building block was subsequently grafted to generate model compound 1, pillar[5]arene 2, and pillar[6]arene 3, bearing two, ten and twelve mesomorphic subunits, respectively. The liquid-crystalline and thermal properties of the compounds were investigated by polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). Comparison of the liquid-crystalline properties of macrocycles 2 and 3 with those of 1 revealed the strong influence of the macrocyclic pillar[n]arene core on the mesomorphic properties. Whereas only a monotropic mesophase was observed for 1, a broad enantiotropic mesophase was evidenced for both pillar[n]arene derivatives.
URI
https://libra.unine.ch/handle/123456789/4667
DOI
10.1002/ejoc.201300356
Autre version
http://dx.doi.org/10.1002/ejoc.201300356
Type de publication
Resource Types::text::journal::journal article
Dossier(s) à télécharger
 main article: Nierengarten_I.-Macrocyclic_effects-20170518140020-ZT.pdf (1.71 MB)
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