Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases

Introducing a rigid linear π-conjugated acetylene linker into a supramolecular building block consisting of a hydrogen-bond donor side and a hydrogen-bond acceptor side yields a decrease in cooperativity in the resulting formed quartet. This follows from our Kohn-Sham molecular orbital and Voronoi d...

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Autores: Almacellas, David, van der Lubbe, Stephanie C. C., Grosch, Alice A., Tsagri, Iris, Fonseca Guerra, Célia, Poater i Teixidor, Jordi
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/218759
Acceso en línea:https://hdl.handle.net/2445/218759
Access Level:acceso abierto
Palabra clave:Hidrogen
ADN
Química supramolecular
Hydrogen
DNA
Supramolecular chemistry
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spelling Cooperativity in Hydrogen-Bonded Macrocycles Derived from NucleobasesAlmacellas, Davidvan der Lubbe, Stephanie C. C.Grosch, Alice A.Tsagri, IrisFonseca Guerra, CéliaPoater i Teixidor, JordiHidrogenADNQuímica supramolecularHydrogenDNASupramolecular chemistryIntroducing a rigid linear π-conjugated acetylene linker into a supramolecular building block consisting of a hydrogen-bond donor side and a hydrogen-bond acceptor side yields a decrease in cooperativity in the resulting formed quartet. This follows from our Kohn-Sham molecular orbital and Voronoi deformation density analyses of hydrogen-bonded macrocycles based on guanine and cytosine nucleobases. The acetylene linker abstracts electron density from the hydrogen-bond acceptor and donor, making the hydrogen-bond acceptor more negatively charged and the hydrogen-bond donor more positively charged and hence suppressing the donor–acceptor charge transfer interaction between the interacting fragments. This, ultimately, hampers the cooperativity in the hydrogen-bonded macrocycle. We envision that these findings could open the door to new design principles for the development of novel hydrogen-bond supramolecular macrocycles.Wiley-VCH2025202520242025info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion10 p.application/pdfhttps://hdl.handle.net/2445/218759Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésReproducció del document publicat a: https://doi.org/10.1002/ejoc.202301164European Journal of Organic Chemistry, 2024, p. e202301164https://doi.org/10.1002/ejoc.202301164cc-by-nc-nd (c) Almacellas, David, et al., 2024http://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccessoai:recercat.cat:2445/2187592026-05-29T05:05:01Z
dc.title.none.fl_str_mv Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
title Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
spellingShingle Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
Almacellas, David
Hidrogen
ADN
Química supramolecular
Hydrogen
DNA
Supramolecular chemistry
title_short Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
title_full Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
title_fullStr Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
title_full_unstemmed Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
title_sort Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases
dc.creator.none.fl_str_mv Almacellas, David
van der Lubbe, Stephanie C. C.
Grosch, Alice A.
Tsagri, Iris
Fonseca Guerra, Célia
Poater i Teixidor, Jordi
author Almacellas, David
author_facet Almacellas, David
van der Lubbe, Stephanie C. C.
Grosch, Alice A.
Tsagri, Iris
Fonseca Guerra, Célia
Poater i Teixidor, Jordi
author_role author
author2 van der Lubbe, Stephanie C. C.
Grosch, Alice A.
Tsagri, Iris
Fonseca Guerra, Célia
Poater i Teixidor, Jordi
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Hidrogen
ADN
Química supramolecular
Hydrogen
DNA
Supramolecular chemistry
topic Hidrogen
ADN
Química supramolecular
Hydrogen
DNA
Supramolecular chemistry
description Introducing a rigid linear π-conjugated acetylene linker into a supramolecular building block consisting of a hydrogen-bond donor side and a hydrogen-bond acceptor side yields a decrease in cooperativity in the resulting formed quartet. This follows from our Kohn-Sham molecular orbital and Voronoi deformation density analyses of hydrogen-bonded macrocycles based on guanine and cytosine nucleobases. The acetylene linker abstracts electron density from the hydrogen-bond acceptor and donor, making the hydrogen-bond acceptor more negatively charged and the hydrogen-bond donor more positively charged and hence suppressing the donor–acceptor charge transfer interaction between the interacting fragments. This, ultimately, hampers the cooperativity in the hydrogen-bonded macrocycle. We envision that these findings could open the door to new design principles for the development of novel hydrogen-bond supramolecular macrocycles.
publishDate 2024
dc.date.none.fl_str_mv 2024
2025
2025
2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/218759
url https://hdl.handle.net/2445/218759
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.1002/ejoc.202301164
European Journal of Organic Chemistry, 2024, p. e202301164
https://doi.org/10.1002/ejoc.202301164
dc.rights.none.fl_str_mv cc-by-nc-nd (c) Almacellas, David, et al., 2024
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by-nc-nd (c) Almacellas, David, et al., 2024
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 10 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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