Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene

Autores
Van Der Meijden, Maarten W.; Gelens, Edith; Murillo Quiros, Natalia Maria; Fuhr, Javier Daniel; Gayone, Julio Esteban; Ascolani, Hugo del Lujan; Wurst, Klaus; Lingenfelder, Magalí Alejandra; Kellogg, Richard M.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatography and the absolute configurations were assigned by comparison of the CD spectra with hexahelicene. The t1/2 value for racemization at 210 °C was approximately 1 hour. Scanning tunneling microscopy (STM) measurements were carried out on enantiopure and racemic samples of aminohelicene on Au(111) under ultrahigh vacuum (UHV) conditions. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.
Fil: Van Der Meijden, Maarten W.. No especifíca;
Fil: Gelens, Edith. No especifíca;
Fil: Murillo Quiros, Natalia Maria. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Fuhr, Javier Daniel. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Gayone, Julio Esteban. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Ascolani, Hugo del Lujan. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Wurst, Klaus. Universidad de Innsbruck; Austria
Fil: Lingenfelder, Magalí Alejandra. Ecole Polytechnique Federale de Lausanne. Max Planck-epfl Center For Molecularnanosciencie And Technology; Francia
Fil: Kellogg, Richard M.. No especifíca;
Materia
CROSS-COUPLING
HELICENES
OPTICAL PROPERTIES
RESOLUTION
SCANNING TUNNELING MICROSCOPY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/180203
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/180203
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexaheliceneVan Der Meijden, Maarten W.Gelens, EdithMurillo Quiros, Natalia MariaFuhr, Javier DanielGayone, Julio EstebanAscolani, Hugo del LujanWurst, KlausLingenfelder, Magalí AlejandraKellogg, Richard M.CROSS-COUPLINGHELICENESOPTICAL PROPERTIESRESOLUTIONSCANNING TUNNELING MICROSCOPYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatography and the absolute configurations were assigned by comparison of the CD spectra with hexahelicene. The t1/2 value for racemization at 210 °C was approximately 1 hour. Scanning tunneling microscopy (STM) measurements were carried out on enantiopure and racemic samples of aminohelicene on Au(111) under ultrahigh vacuum (UHV) conditions. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.Fil: Van Der Meijden, Maarten W.. No especifíca;Fil: Gelens, Edith. No especifíca;Fil: Murillo Quiros, Natalia Maria. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; ArgentinaFil: Fuhr, Javier Daniel. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; ArgentinaFil: Gayone, Julio Esteban. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; ArgentinaFil: Ascolani, Hugo del Lujan. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; ArgentinaFil: Wurst, Klaus. Universidad de Innsbruck; AustriaFil: Lingenfelder, Magalí Alejandra. Ecole Polytechnique Federale de Lausanne. Max Planck-epfl Center For Molecularnanosciencie And Technology; FranciaFil: Kellogg, Richard M.. No especifíca;Wiley VCH Verlag2015-12info: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/11336/180203Van Der Meijden, Maarten W.; Gelens, Edith; Murillo Quiros, Natalia Maria; Fuhr, Javier Daniel; Gayone, Julio Esteban; et al.; Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene; Wiley VCH Verlag; Chemistry- A European Journal; 22; 4; 12-2015; 1484-14920947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.201502798/fullinfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201502798info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:39:38Zoai:ri.conicet.gov.ar:11336/180203instacron: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 15:39:38.851CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
title Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
spellingShingle Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
Van Der Meijden, Maarten W.
CROSS-COUPLING
HELICENES
OPTICAL PROPERTIES
RESOLUTION
SCANNING TUNNELING MICROSCOPY
title_short Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
title_full Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
title_fullStr Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
title_full_unstemmed Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
title_sort Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
dc.creator.none.fl_str_mv Van Der Meijden, Maarten W.
Gelens, Edith
Murillo Quiros, Natalia Maria
Fuhr, Javier Daniel
Gayone, Julio Esteban
Ascolani, Hugo del Lujan
Wurst, Klaus
Lingenfelder, Magalí Alejandra
Kellogg, Richard M.
author Van Der Meijden, Maarten W.
author_facet Van Der Meijden, Maarten W.
Gelens, Edith
Murillo Quiros, Natalia Maria
Fuhr, Javier Daniel
Gayone, Julio Esteban
Ascolani, Hugo del Lujan
Wurst, Klaus
Lingenfelder, Magalí Alejandra
Kellogg, Richard M.
author_role author
author2 Gelens, Edith
Murillo Quiros, Natalia Maria
Fuhr, Javier Daniel
Gayone, Julio Esteban
Ascolani, Hugo del Lujan
Wurst, Klaus
Lingenfelder, Magalí Alejandra
Kellogg, Richard M.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv CROSS-COUPLING
HELICENES
OPTICAL PROPERTIES
RESOLUTION
SCANNING TUNNELING MICROSCOPY
topic CROSS-COUPLING
HELICENES
OPTICAL PROPERTIES
RESOLUTION
SCANNING TUNNELING MICROSCOPY
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 convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatography and the absolute configurations were assigned by comparison of the CD spectra with hexahelicene. The t1/2 value for racemization at 210 °C was approximately 1 hour. Scanning tunneling microscopy (STM) measurements were carried out on enantiopure and racemic samples of aminohelicene on Au(111) under ultrahigh vacuum (UHV) conditions. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.
Fil: Van Der Meijden, Maarten W.. No especifíca;
Fil: Gelens, Edith. No especifíca;
Fil: Murillo Quiros, Natalia Maria. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Fuhr, Javier Daniel. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Gayone, Julio Esteban. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Ascolani, Hugo del Lujan. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte; Argentina
Fil: Wurst, Klaus. Universidad de Innsbruck; Austria
Fil: Lingenfelder, Magalí Alejandra. Ecole Polytechnique Federale de Lausanne. Max Planck-epfl Center For Molecularnanosciencie And Technology; Francia
Fil: Kellogg, Richard M.. No especifíca;
description A convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatography and the absolute configurations were assigned by comparison of the CD spectra with hexahelicene. The t1/2 value for racemization at 210 °C was approximately 1 hour. Scanning tunneling microscopy (STM) measurements were carried out on enantiopure and racemic samples of aminohelicene on Au(111) under ultrahigh vacuum (UHV) conditions. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.
publishDate 2015
dc.date.none.fl_str_mv 2015-12
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/11336/180203
Van Der Meijden, Maarten W.; Gelens, Edith; Murillo Quiros, Natalia Maria; Fuhr, Javier Daniel; Gayone, Julio Esteban; et al.; Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene; Wiley VCH Verlag; Chemistry- A European Journal; 22; 4; 12-2015; 1484-1492
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/180203
identifier_str_mv Van Der Meijden, Maarten W.; Gelens, Edith; Murillo Quiros, Natalia Maria; Fuhr, Javier Daniel; Gayone, Julio Esteban; et al.; Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene; Wiley VCH Verlag; Chemistry- A European Journal; 22; 4; 12-2015; 1484-1492
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.201502798/full
info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201502798
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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
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score 13.22299

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