Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers

The development of synthetic strategies to engineer π-conjugated polymers is of paramount importance in modern chemistry and materials science. Here we introduce a synthetic protocol based on the search for specific vibrational modes through an appropriate tailoring of the π-conjugation of the precu...

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Autores: De la Torre, Bruno, Adam Matěj, Adam, Sánchez-Grande, Ana, Cirera, Borja, Mallada, Benjamín, Rodríguez-Sánchez, Eider, Santos Barahona, José Manuel, Mendieta-Moreno, Jesús, Edalatmanesh, Shayan, Lauwaet, Koen, Otyepka, Michal, Medveď, Miroslav, Buendía, Álvaro, Miranda, Rodolfo, Martín León, Nazario, Pavel, Jelínek, Écij, David
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/92479
Acceso en línea:https://hdl.handle.net/20.500.14352/92479
Access Level:acceso abierto
Palabra clave:547
Química orgánica (Química)
2306 Química Orgánica
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spelling Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymersDe la Torre, BrunoAdam Matěj, AdamSánchez-Grande, AnaCirera, BorjaMallada, BenjamínRodríguez-Sánchez, EiderSantos Barahona, José ManuelMendieta-Moreno, JesúsEdalatmanesh, ShayanLauwaet, KoenOtyepka, MichalMedveď, MiroslavBuendía, ÁlvaroMiranda, RodolfoMartín León, NazarioPavel, JelínekÉcij, David547Química orgánica (Química)2306 Química OrgánicaThe development of synthetic strategies to engineer π-conjugated polymers is of paramount importance in modern chemistry and materials science. Here we introduce a synthetic protocol based on the search for specific vibrational modes through an appropriate tailoring of the π-conjugation of the precursors, in order to increase the attempt frequency of a chemical reaction. First, we design a 1D π-conjugated polymer on Au(111), which is based on bisanthene monomers linked by cumulene bridges that tune specific vibrational modes. In a second step, upon further annealing, such vibrational modes steer the twofold cyclization reaction between adjacent bisanthene moieties, which gives rise to a long pentalene-bridged conjugated ladder polymer featuring a low bandgap. In addition, high resolution atomic force microscopy allows us to identify by atomistic insights the resonance form of the polymer, thus confirming the validity of the Glidewell and Lloyd´s rules for aromaticity. This on-surface synthetic strategy may stimulate exploiting previously precluded reactions towards π-conjugated polymers with specific structures and properties.Springer NatureUniversidad Complutense de Madrid20202020-01-0120202020-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/92479reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/924792026-06-02T12:44:21Z
dc.title.none.fl_str_mv Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
title Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
spellingShingle Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
De la Torre, Bruno
547
Química orgánica (Química)
2306 Química Orgánica
title_short Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
title_full Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
title_fullStr Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
title_full_unstemmed Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
title_sort Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers
dc.creator.none.fl_str_mv De la Torre, Bruno
Adam Matěj, Adam
Sánchez-Grande, Ana
Cirera, Borja
Mallada, Benjamín
Rodríguez-Sánchez, Eider
Santos Barahona, José Manuel
Mendieta-Moreno, Jesús
Edalatmanesh, Shayan
Lauwaet, Koen
Otyepka, Michal
Medveď, Miroslav
Buendía, Álvaro
Miranda, Rodolfo
Martín León, Nazario
Pavel, Jelínek
Écij, David
author De la Torre, Bruno
author_facet De la Torre, Bruno
Adam Matěj, Adam
Sánchez-Grande, Ana
Cirera, Borja
Mallada, Benjamín
Rodríguez-Sánchez, Eider
Santos Barahona, José Manuel
Mendieta-Moreno, Jesús
Edalatmanesh, Shayan
Lauwaet, Koen
Otyepka, Michal
Medveď, Miroslav
Buendía, Álvaro
Miranda, Rodolfo
Martín León, Nazario
Pavel, Jelínek
Écij, David
author_role author
author2 Adam Matěj, Adam
Sánchez-Grande, Ana
Cirera, Borja
Mallada, Benjamín
Rodríguez-Sánchez, Eider
Santos Barahona, José Manuel
Mendieta-Moreno, Jesús
Edalatmanesh, Shayan
Lauwaet, Koen
Otyepka, Michal
Medveď, Miroslav
Buendía, Álvaro
Miranda, Rodolfo
Martín León, Nazario
Pavel, Jelínek
Écij, David
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Química orgánica (Química)
2306 Química Orgánica
topic 547
Química orgánica (Química)
2306 Química Orgánica
description The development of synthetic strategies to engineer π-conjugated polymers is of paramount importance in modern chemistry and materials science. Here we introduce a synthetic protocol based on the search for specific vibrational modes through an appropriate tailoring of the π-conjugation of the precursors, in order to increase the attempt frequency of a chemical reaction. First, we design a 1D π-conjugated polymer on Au(111), which is based on bisanthene monomers linked by cumulene bridges that tune specific vibrational modes. In a second step, upon further annealing, such vibrational modes steer the twofold cyclization reaction between adjacent bisanthene moieties, which gives rise to a long pentalene-bridged conjugated ladder polymer featuring a low bandgap. In addition, high resolution atomic force microscopy allows us to identify by atomistic insights the resonance form of the polymer, thus confirming the validity of the Glidewell and Lloyd´s rules for aromaticity. This on-surface synthetic strategy may stimulate exploiting previously precluded reactions towards π-conjugated polymers with specific structures and properties.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020-01-01
2020
2020-01-01
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/20.500.14352/92479
url https://hdl.handle.net/20.500.14352/92479
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
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
Attribution-NonCommercial-NoDerivatives 4.0 International
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 Springer Nature
publisher.none.fl_str_mv Springer Nature
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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