Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces

Antiaromatic and open-shell molecules are attractive because of their distinct electronic and magnetic behaviour. However, their increased reactivity creates a challenge for probing their properties. Here, we describe the on-surface and in-solution generation and characterisation of a highly reactiv...

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Authors: Mjazik, Zsolt, Pavliček, Niko, Vilas-Varela, Manuel, Pérez Meirás, María Dolores, Moll, Nikolaj, Guitián Rivera, Enrique, Meyer, Gehrard, Peña Gil, Diego, Gross, Leo
Format: article
Publication Date:2018
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:minerva.usc.gal:10347/16779
Online Access:http://hdl.handle.net/10347/16779
Access Level:Open access
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spelling Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfacesMjazik, ZsoltPavliček, NikoVilas-Varela, ManuelPérez Meirás, María DoloresMoll, NikolajGuitián Rivera, EnriqueMeyer, GehrardPeña Gil, DiegoGross, LeoAntiaromatic and open-shell molecules are attractive because of their distinct electronic and magnetic behaviour. However, their increased reactivity creates a challenge for probing their properties. Here, we describe the on-surface and in-solution generation and characterisation of a highly reactive antiaromatic molecule: indeno[1,2-b]fluorene (IF). In solution, we generated IF by KI-induced dehalogenation of a dibromo-substituted precursor molecule and found that IF survives for minutes at ambient conditions. Using atom manipulation at low temperatures we generated IF on Cu(111) and on bilayer NaCl. On these surfaces, we characterised IF by bond-order analysis using non-contact atomic force microscopy with CO-functionalised tips and by orbital imaging using scanning tunnelling microscopy. We found that the closed-shell configuration and antiaromatic character predicted for gas-phase IF are preserved on the NaCl film. On Cu(111), we observed significant bond-order reorganisation within the s-indacene moiety because of chemisorption, highlighting the importance of molecule surface interactions on the π-electron distributionSpringer NatureUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais MolecularesUniversidade de Santiago de Compostela. Departamento de Química Orgánica20182018-03-2220182018-03-22journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10347/16779reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostelainstname:Universidad de Santiago de Compostela (USC)InglésengMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 MAT2016-78293-C6-3-RMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2016-78157-Ropen accesshttp://purl.org/coar/access_right/c_abf2© The Author(s) 2018. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/ licenses/by/4.0/http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:minerva.usc.gal:10347/167792026-06-15T12:47:27Z
dc.title.none.fl_str_mv Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
title Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
spellingShingle Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
Mjazik, Zsolt
title_short Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
title_full Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
title_fullStr Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
title_full_unstemmed Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
title_sort Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces
dc.creator.none.fl_str_mv Mjazik, Zsolt
Pavliček, Niko
Vilas-Varela, Manuel
Pérez Meirás, María Dolores
Moll, Nikolaj
Guitián Rivera, Enrique
Meyer, Gehrard
Peña Gil, Diego
Gross, Leo
author Mjazik, Zsolt
author_facet Mjazik, Zsolt
Pavliček, Niko
Vilas-Varela, Manuel
Pérez Meirás, María Dolores
Moll, Nikolaj
Guitián Rivera, Enrique
Meyer, Gehrard
Peña Gil, Diego
Gross, Leo
author_role author
author2 Pavliček, Niko
Vilas-Varela, Manuel
Pérez Meirás, María Dolores
Moll, Nikolaj
Guitián Rivera, Enrique
Meyer, Gehrard
Peña Gil, Diego
Gross, Leo
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
Universidade de Santiago de Compostela. Departamento de Química Orgánica
description Antiaromatic and open-shell molecules are attractive because of their distinct electronic and magnetic behaviour. However, their increased reactivity creates a challenge for probing their properties. Here, we describe the on-surface and in-solution generation and characterisation of a highly reactive antiaromatic molecule: indeno[1,2-b]fluorene (IF). In solution, we generated IF by KI-induced dehalogenation of a dibromo-substituted precursor molecule and found that IF survives for minutes at ambient conditions. Using atom manipulation at low temperatures we generated IF on Cu(111) and on bilayer NaCl. On these surfaces, we characterised IF by bond-order analysis using non-contact atomic force microscopy with CO-functionalised tips and by orbital imaging using scanning tunnelling microscopy. We found that the closed-shell configuration and antiaromatic character predicted for gas-phase IF are preserved on the NaCl film. On Cu(111), we observed significant bond-order reorganisation within the s-indacene moiety because of chemisorption, highlighting the importance of molecule surface interactions on the π-electron distribution
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-03-22
2018
2018-03-22
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 http://hdl.handle.net/10347/16779
url http://hdl.handle.net/10347/16779
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 MAT2016-78293-C6-3-R
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2016-78157-R
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
http://creativecommons.org/licenses/by/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/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Springer Nature
publisher.none.fl_str_mv Springer Nature
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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