Artículo
A convenient synthesis of a 2,7-difunctional tetra(alkoxy)triphenylene involving 4,4′- diacetoxy-3,3′-dialkoxybiphenyl as a key precursor and its conversion to extended hybrid mesogenic compounds
Zelcer, Andrés
; Cecchi, Florencia
; Alborés, Pablo
; Guillon, Daniel; Heinrich, Bennoît; Donnio, Bertrand; Cukiernik, Fabio Daniel
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Fecha de publicación:
03/06/2013
Editorial:
Taylor & Francis Ltd
Revista:
Liquid Crystals
ISSN:
0267-8292
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A new rational pathway to 2,7-difunctionalised-β-hexa-substituted triphenylenes is presented, requiring less protection/deprotection and purification steps than more conventional synthetic procedures in the framework of the ‘biphenyl route’. Main improvements are deprotection via alkaline hydrolysis of an ester in ethanol/water medium instead of using toxic and pyrophoric reagents like lithium diphenylphosphide, and the use of easily prepared brominated precursors instead of iodinated reagents for biphenyl synthesis. 4,4′-Diacetoxy-3,3′-bis(hexyloxy)biphenyl has been synthesised under this scheme, and characterised by proton nuclear magnetic resonance (1H NMR) spectrometry, elemental analysis and single-crystal crystallography. It crystallises in the P-1 space group, and exhibits a layered structure built-up through dipolar, C–H … π and C–H … O=C non-covalent interactions. This compound has been oxidatively coupled with 1,2-bis(hexyloxy)benzene to yield 2,7-dihydroxy-3,6,10,11-tetrakis(hexyloxy)triphenylene, a non-mesogen key precursor for the synthesis of the corresponding liquid-crystalline 2,7-difunctional triphenylenes. Indeed, a reactive 2,7-difunctional mesogen was prepared and used to produce new triphenylene-siloxane hybrid monomeric, trimeric and polymeric mesogens. All of them exhibited columnar hexagonal (Colh) mesophases.
Palabras clave:
Liquid Crystals
,
Triphenylenes
,
Biphenyl Route
,
Siloxane
,
Polymer
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Articulos(INQUIMAE)
Articulos de INST.D/QUIM FIS D/L MATERIALES MEDIOAMB Y ENERGIA
Articulos de INST.D/QUIM FIS D/L MATERIALES MEDIOAMB Y ENERGIA
Articulos(SEDE CENTRAL)
Articulos de SEDE CENTRAL
Articulos de SEDE CENTRAL
Citación
Zelcer, Andrés; Cecchi, Florencia; Alborés, Pablo; Guillon, Daniel; Heinrich, Bennoît; et al.; A convenient synthesis of a 2,7-difunctional tetra(alkoxy)triphenylene involving 4,4′- diacetoxy-3,3′-dialkoxybiphenyl as a key precursor and its conversion to extended hybrid mesogenic compounds; Taylor & Francis Ltd; Liquid Crystals; 40; 8; 3-6-2013; 1121-1134
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