Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene

In this work, we present an efficient synthetic methodology that allows precise and selective control on the C–C bonds during the Scholl reaction. The first ever described hexabenzocoronene (HBC)-containing helical twistacene NG2 has been obtained with very high yield and practically no need for pur...

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Authors: Mora Fuentes, Juan Pedro, Villar Castro, Daniel, Barbosa de Bessa, J. Francisco, Aranda Ruiz, Daniel, Hampel, Frank, Pérez Meirás, María Dolores, Pérez Ojeda, M. Eugenia, Peña Gil, Diego, Hirsch, Andreas
Format: article
Publication Date:2026
Country:España
Institution:Universidad de Santiago de Compostela (USC)
Repository:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Language:English
OAI Identifier:oai:dnet:minerva_____::71e2e61fc572ab622653cfa7eb27818e
Online Access:https://hdl.handle.net/10347/46773
Access Level:Open access
Keyword:Bottom-up approach
Nanographenes
Scholl reaction
Soluble
Twistacenes
Investigación
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spelling Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical TwistaceneMora Fuentes, Juan PedroVillar Castro, DanielBarbosa de Bessa, J. FranciscoAranda Ruiz, DanielHampel, FrankPérez Meirás, María DoloresPérez Ojeda, M. EugeniaPeña Gil, DiegoHirsch, AndreasBottom-up approachNanographenesScholl reactionSolubleTwistacenesInvestigaciónIn this work, we present an efficient synthetic methodology that allows precise and selective control on the C–C bonds during the Scholl reaction. The first ever described hexabenzocoronene (HBC)-containing helical twistacene NG2 has been obtained with very high yield and practically no need for purification, starting from a helical-twisted hexacene NG1. X-ray analysis reveals an end-to-end twist angle, from approximately 145° in NG1 to 132° in NG2. This approach has provided access to nanographenes (NGs) with improved properties compared to their planar analogues, in particular, enhanced solubility and high stability. In addition, they exhibit interesting redox properties, which, together with their high molar absorbance and optimal energy levels, highlight their potential as new organic semiconductor materials for emerging photovoltaic and electronic technologies.WileyUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)Universidade de Santiago de Compostela. Departamento de Química Orgánica20262026-02-1520262026-02-15journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10347/46773reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostelainstname:Universidad de Santiago de Compostela (USC)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2022-140845OB-C62 DISEÑO Y SINTESIS DE PRECURSORES PARA LA PREPARACION DE NANOESTRUCTURAS MOLECULARES FUNCIONALESopen accesshttp://purl.org/coar/access_right/c_abf2© 2026 The Author(s). Chemistry –A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:dnet:minerva_____::71e2e61fc572ab622653cfa7eb27818e2026-06-15T12:47:27Z
dc.title.none.fl_str_mv Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
title Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
spellingShingle Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
Mora Fuentes, Juan Pedro
Bottom-up approach
Nanographenes
Scholl reaction
Soluble
Twistacenes
Investigación
title_short Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
title_full Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
title_fullStr Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
title_full_unstemmed Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
title_sort Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene
dc.creator.none.fl_str_mv Mora Fuentes, Juan Pedro
Villar Castro, Daniel
Barbosa de Bessa, J. Francisco
Aranda Ruiz, Daniel
Hampel, Frank
Pérez Meirás, María Dolores
Pérez Ojeda, M. Eugenia
Peña Gil, Diego
Hirsch, Andreas
author Mora Fuentes, Juan Pedro
author_facet Mora Fuentes, Juan Pedro
Villar Castro, Daniel
Barbosa de Bessa, J. Francisco
Aranda Ruiz, Daniel
Hampel, Frank
Pérez Meirás, María Dolores
Pérez Ojeda, M. Eugenia
Peña Gil, Diego
Hirsch, Andreas
author_role author
author2 Villar Castro, Daniel
Barbosa de Bessa, J. Francisco
Aranda Ruiz, Daniel
Hampel, Frank
Pérez Meirás, María Dolores
Pérez Ojeda, M. Eugenia
Peña Gil, Diego
Hirsch, Andreas
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Universidade de Santiago de Compostela. Departamento de Química Orgánica
dc.subject.none.fl_str_mv Bottom-up approach
Nanographenes
Scholl reaction
Soluble
Twistacenes
Investigación
topic Bottom-up approach
Nanographenes
Scholl reaction
Soluble
Twistacenes
Investigación
description In this work, we present an efficient synthetic methodology that allows precise and selective control on the C–C bonds during the Scholl reaction. The first ever described hexabenzocoronene (HBC)-containing helical twistacene NG2 has been obtained with very high yield and practically no need for purification, starting from a helical-twisted hexacene NG1. X-ray analysis reveals an end-to-end twist angle, from approximately 145° in NG1 to 132° in NG2. This approach has provided access to nanographenes (NGs) with improved properties compared to their planar analogues, in particular, enhanced solubility and high stability. In addition, they exhibit interesting redox properties, which, together with their high molar absorbance and optimal energy levels, highlight their potential as new organic semiconductor materials for emerging photovoltaic and electronic technologies.
publishDate 2026
dc.date.none.fl_str_mv 2026
2026-02-15
2026
2026-02-15
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10347/46773
url https://hdl.handle.net/10347/46773
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2022-140845OB-C62 DISEÑO Y SINTESIS DE PRECURSORES PARA LA PREPARACION DE NANOESTRUCTURAS MOLECULARES FUNCIONALES
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
instname:Universidad de Santiago de Compostela (USC)
instname_str Universidad de Santiago de Compostela (USC)
reponame_str Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
collection Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812455

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