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Abstract:

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. © 2013 Copyright Taylor and Francis Group, LLC.

Registro:

Documento: Artículo
Título: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
Autor:Zelcer, A.; Cecchi, F.; Alborés, P.; Guillon, D.; Heinrich, B.; Donnio, B.; Cukiernik, F.D.
Filiación:INQUIMAE, Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina
Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), UMR 7504 (CNRS-Université de Strasbourg), 67034 Strasbourg Cedex 2, France
Gerencia Química, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Av. Gral Paz 1499, B1650KNA, San Martín, Buenos Aires, Argentina
Palabras clave:biphenyl route; liquid crystals; polymer; siloxane; triphenylenes
Año:2013
Volumen:40
Número:8
Página de inicio:1121
Página de fin:1134
DOI: http://dx.doi.org/10.1080/02678292.2013.795623
Título revista:Liquid Crystals
Título revista abreviado:Liq. Cryst.
ISSN:02678292
CODEN:LICRE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02678292_v40_n8_p1121_Zelcer

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Citas:

---------- APA ----------
Zelcer, A., Cecchi, F., Alborés, P., Guillon, D., Heinrich, B., Donnio, B. & Cukiernik, F.D. (2013) . 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. Liquid Crystals, 40(8), 1121-1134.
http://dx.doi.org/10.1080/02678292.2013.795623
---------- CHICAGO ----------
Zelcer, A., Cecchi, F., Alborés, P., Guillon, D., Heinrich, B., Donnio, B., 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" . Liquid Crystals 40, no. 8 (2013) : 1121-1134.
http://dx.doi.org/10.1080/02678292.2013.795623
---------- MLA ----------
Zelcer, A., Cecchi, F., Alborés, P., Guillon, D., Heinrich, B., Donnio, B., 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" . Liquid Crystals, vol. 40, no. 8, 2013, pp. 1121-1134.
http://dx.doi.org/10.1080/02678292.2013.795623
---------- VANCOUVER ----------
Zelcer, A., Cecchi, F., Alborés, P., Guillon, D., Heinrich, B., Donnio, B., 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. Liq. Cryst. 2013;40(8):1121-1134.
http://dx.doi.org/10.1080/02678292.2013.795623