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 hydrolysis...

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Detalhes bibliográficos
Autores: Zelcer, Andrés, Cecchi, Florencia, Alborés, Pablo, Guillon, Daniel, Heinrich, Bennoît, Donnio, Bertrand, Cukiernik, Fabio Daniel
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/7889
Acesso em linha:http://hdl.handle.net/11336/7889
Access Level:acceso abierto
Palavra-chave:Liquid Crystals
Triphenylenes
Biphenyl Route
Siloxane
Polymer
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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oai_identifier_str oai:ri.conicet.gov.ar:11336/7889
network_acronym_str AR
network_name_str Argentina
repository_id_str
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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Liquid Crystals
Triphenylenes
Biphenyl Route
Siloxane
Polymer
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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_ 1799195038622679040
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 Técnicas2024-05-08T13:42:00Zoai: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:34982024-05-08 13:42:00.775CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
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