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 meso...

Autores: Zelcer, Andrés; Cecchi, Florencia; Alborés, Pablo; Guillon, Daniel; Heinrich, Bennoît; Donnio, Bertrand; Cukiernik, Fabio Daniel
Año de publicación: 2013
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: 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.
Fil: Zelcer, Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina
Fil: Cecchi, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina
Fil: Alborés, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina
Fil: Guillon, Daniel. Universite de Strasbourg; Francia
Fil: Heinrich, Bennoît. Universite de Strasbourg; Francia
Fil: Donnio, Bertrand. Universite de Strasbourg; Francia
Fil: Cukiernik, Fabio Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina
Materia: Liquid Crystals
Triphenylenes
Biphenyl Route
Siloxane
Polymer
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/7889

Acceder

id	CONICETDig_9bb08d8212d72030aca0c9bdba0d3f2e
oai_identifier_str	oai:ri.conicet.gov.ar:11336/7889
network_acronym_str	CONICETDig
repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	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 compoundsZelcer, AndrésCecchi, FlorenciaAlborés, PabloGuillon, DanielHeinrich, BennoîtDonnio, BertrandCukiernik, Fabio DanielLiquid CrystalsTriphenylenesBiphenyl RouteSiloxanePolymerhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A 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.Fil: Zelcer, Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; ArgentinaFil: Cecchi, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; ArgentinaFil: Alborés, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; ArgentinaFil: Guillon, Daniel. Universite de Strasbourg; FranciaFil: Heinrich, Bennoît. Universite de Strasbourg; FranciaFil: Donnio, Bertrand. Universite de Strasbourg; FranciaFil: Cukiernik, Fabio Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; ArgentinaTaylor & Francis Ltd2013-06-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/7889Zelcer, 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; 1121-11340267-8292enginfo:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1080/02678292.2013.795623info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/abs/10.1080/02678292.2013.795623info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:37:52Zoai:ri.conicet.gov.ar:11336/7889instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:37:52.545CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	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	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
spellingShingle	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 Liquid Crystals Triphenylenes Biphenyl Route Siloxane Polymer
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	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
dc.creator.none.fl_str_mv	Zelcer, Andrés Cecchi, Florencia Alborés, Pablo Guillon, Daniel Heinrich, Bennoît Donnio, Bertrand Cukiernik, Fabio Daniel
author	Zelcer, Andrés
author_facet	Zelcer, Andrés Cecchi, Florencia Alborés, Pablo Guillon, Daniel Heinrich, Bennoît Donnio, Bertrand Cukiernik, Fabio Daniel
author_role	author
author2	Cecchi, Florencia Alborés, Pablo Guillon, Daniel Heinrich, Bennoît Donnio, Bertrand Cukiernik, Fabio Daniel
author2_role	author author author author author author
dc.subject.none.fl_str_mv	Liquid Crystals Triphenylenes Biphenyl Route Siloxane Polymer
topic	Liquid Crystals Triphenylenes Biphenyl Route Siloxane Polymer
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	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. Fil: Zelcer, Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina Fil: Cecchi, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina Fil: Alborés, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina Fil: Guillon, Daniel. Universite de Strasbourg; Francia Fil: Heinrich, Bennoît. Universite de Strasbourg; Francia Fil: Donnio, Bertrand. Universite de Strasbourg; Francia Fil: Cukiernik, Fabio Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires; Argentina
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.
publishDate	2013
dc.date.none.fl_str_mv	2013-06-03
dc.type.none.fl_str_mv	info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo
format	article
status_str	publishedVersion
dc.identifier.none.fl_str_mv	http://hdl.handle.net/11336/7889 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 0267-8292
url	http://hdl.handle.net/11336/7889
identifier_str_mv	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 0267-8292
dc.language.none.fl_str_mv	eng
language	eng
dc.relation.none.fl_str_mv	info:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1080/02678292.2013.795623 info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/abs/10.1080/02678292.2013.795623
dc.rights.none.fl_str_mv	info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv	openAccess
rights_invalid_str_mv	https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv	application/pdf application/pdf application/pdf application/pdf
dc.publisher.none.fl_str_mv	Taylor & Francis Ltd
publisher.none.fl_str_mv	Taylor & Francis Ltd
dc.source.none.fl_str_mv	reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str	CONICET Digital (CONICET)
collection	CONICET Digital (CONICET)
instname_str	Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv	CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv	dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_	1846082854452199424
score	13.22299

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 meso...

Publicaciones similares