Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings

The synthesis of a series of triangular-shaped tricarboxamides endowed with three picoline or nicotine units (compounds 2 and 3, respectively) or just one nicotine unit (compound 4) is reported, and their selfassembling features investigated. The pyridine rings make compounds 2–4 electronically comp...

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Detalles Bibliográficos
Autores: López-Gandul, Lucía, Morón-Blanco, Adrián, García Melo, Fátima, Sánchez Martín, Luis
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/88820
Acceso en línea:https://hdl.handle.net/20.500.14352/88820
Access Level:acceso abierto
Palabra clave:547
Química orgánica (Química)
23 Química
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oai_identifier_str oai:docta.ucm.es:20.500.14352/88820
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spelling Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine ringsLópez-Gandul, LucíaMorón-Blanco, AdriánGarcía Melo, FátimaSánchez Martín, Luis547Química orgánica (Química)23 QuímicaThe synthesis of a series of triangular-shaped tricarboxamides endowed with three picoline or nicotine units (compounds 2 and 3, respectively) or just one nicotine unit (compound 4) is reported, and their selfassembling features investigated. The pyridine rings make compounds 2–4 electronically complementary with our previously reported oligo(phenylene ethynylene)tricarboxamides (OPE-TA) 1 to form supramolecular copolymers. C3-symmetric tricarboxamide 2 forms highly stable intramolecular five-membered pseudocycles that impede its supramolecular polymerization into poly-2 and the co-assembly with 1 to yield copolymer poly-1-co-2. On the other hand, C3-symmetric tricarboxamide 3 readily forms poly-3 with great stability but unable to form helical supramolecular polymers despite the presence of the peripheral chiral side chains. The copolymer poly-1-co-3 can only be obtained by a previous complete disassembly of the constitutive homopolymers in CHCl3. Helical poly-1-co-3 arises in a process involving the transfer of the helicity from racemic poly-1 to poly-3, and the amplification of asymmetry from chiral poly-3 to poly-1. Importantly, C2v symmetric 4, endowed with only one nicotinamide moiety and three chiral side chains, self-assembles into a P-type helical supramolecular polymer (poly-4) in a thermodynamically controlled cooperative process. The combination of poly-1 and poly-4 generates chiral supramolecular copolymer poly-1-co-4, whose blocky microstructure has been investigated by applying the previously reported supramolecular copolymerization model.WileyUniversidad Complutense de Madrid20232023-01-0120232023-01-01journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/88820reponame: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:20.500.14352/888202026-06-02T12:44:21Z
dc.title.none.fl_str_mv Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
title Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
spellingShingle Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
López-Gandul, Lucía
547
Química orgánica (Química)
23 Química
title_short Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
title_full Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
title_fullStr Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
title_full_unstemmed Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
title_sort Supramolecular block copolymers from tricarboxamides. Biasing co-assembly by the incorporation of pyridine rings
dc.creator.none.fl_str_mv López-Gandul, Lucía
Morón-Blanco, Adrián
García Melo, Fátima
Sánchez Martín, Luis
author López-Gandul, Lucía
author_facet López-Gandul, Lucía
Morón-Blanco, Adrián
García Melo, Fátima
Sánchez Martín, Luis
author_role author
author2 Morón-Blanco, Adrián
García Melo, Fátima
Sánchez Martín, Luis
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Química orgánica (Química)
23 Química
topic 547
Química orgánica (Química)
23 Química
description The synthesis of a series of triangular-shaped tricarboxamides endowed with three picoline or nicotine units (compounds 2 and 3, respectively) or just one nicotine unit (compound 4) is reported, and their selfassembling features investigated. The pyridine rings make compounds 2–4 electronically complementary with our previously reported oligo(phenylene ethynylene)tricarboxamides (OPE-TA) 1 to form supramolecular copolymers. C3-symmetric tricarboxamide 2 forms highly stable intramolecular five-membered pseudocycles that impede its supramolecular polymerization into poly-2 and the co-assembly with 1 to yield copolymer poly-1-co-2. On the other hand, C3-symmetric tricarboxamide 3 readily forms poly-3 with great stability but unable to form helical supramolecular polymers despite the presence of the peripheral chiral side chains. The copolymer poly-1-co-3 can only be obtained by a previous complete disassembly of the constitutive homopolymers in CHCl3. Helical poly-1-co-3 arises in a process involving the transfer of the helicity from racemic poly-1 to poly-3, and the amplification of asymmetry from chiral poly-3 to poly-1. Importantly, C2v symmetric 4, endowed with only one nicotinamide moiety and three chiral side chains, self-assembles into a P-type helical supramolecular polymer (poly-4) in a thermodynamically controlled cooperative process. The combination of poly-1 and poly-4 generates chiral supramolecular copolymer poly-1-co-4, whose blocky microstructure has been investigated by applying the previously reported supramolecular copolymerization model.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-01-01
2023
2023-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/88820
url https://hdl.handle.net/20.500.14352/88820
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 Wiley
publisher.none.fl_str_mv Wiley
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 15,301603

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