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

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...

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Autores principales: Zelcer, Andrés, Cecchi, Florencia, Albores, Pablo, Cukiernik, Fabio Daniel
Publicado: 2013
Materias:
biphenyl route
liquid crystals
polymer
siloxane
triphenylenes
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02678292_v40_n8_p1121_Zelcer
http://hdl.handle.net/20.500.12110/paper_02678292_v40_n8_p1121_Zelcer
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_02678292_v40_n8_p1121_Zelcer
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spelling paper:paper_02678292_v40_n8_p1121_Zelcer2023-06-08T15:23:40Z 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 Albores, Pablo Cukiernik, Fabio Daniel biphenyl route liquid crystals polymer siloxane triphenylenes 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. Fil:Zelcer, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cecchi, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Alborés, P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cukiernik, F.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02678292_v40_n8_p1121_Zelcer http://hdl.handle.net/20.500.12110/paper_02678292_v40_n8_p1121_Zelcer
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic biphenyl route
liquid crystals
polymer
siloxane
triphenylenes
spellingShingle biphenyl route
liquid crystals
polymer
siloxane
triphenylenes
Zelcer, Andrés
Cecchi, Florencia
Albores, Pablo
Cukiernik, Fabio Daniel
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
topic_facet biphenyl route
liquid crystals
polymer
siloxane
triphenylenes
description 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.
author Zelcer, Andrés
Cecchi, Florencia
Albores, Pablo
Cukiernik, Fabio Daniel
author_facet Zelcer, Andrés
Cecchi, Florencia
Albores, Pablo
Cukiernik, Fabio Daniel
author_sort Zelcer, Andrés
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publishDate 2013
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02678292_v40_n8_p1121_Zelcer
http://hdl.handle.net/20.500.12110/paper_02678292_v40_n8_p1121_Zelcer
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