Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis

Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take...

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Autores: Arlegui Chamizo, Aitor, Torres, Pol, Cuesta Turienzo, Víctor, Crusats i Aliguer, Joaquim, Moyano i Baldoire, Albert
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2020
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:2445/175864
Acceso en línea:https://hdl.handle.net/2445/175864
Access Level:acceso abierto
Palabra clave:Porfirines
Catàlisi
Reacció aldòlica
Porphyrins
Catalysis
Aldol reaction
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spelling Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysisArlegui Chamizo, AitorTorres, PolCuesta Turienzo, VíctorCrusats i Aliguer, JoaquimMoyano i Baldoire, AlbertPorfirinesCatàlisiReacció aldòlicaPorphyrinsCatalysisAldol reactionTwo chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take place, whereas under acidic conditions, the porphyrinic protonated core of the hybrid leads to the formation of self-assembled structures, so that the hybrids flocculate and their catalytic activity is fully suppressed. The low degree of chirality transfer observed for aqueous Michael and aldol reactions strongly suggests that these reactions take place under true "in water" organocatalytic conditions. The highly insoluble catalyst aggregates can easily be separated from the reaction products by centrifugation of the acidic reaction mixtures, and after neutralization and desalting, the sodium salts of the sulfonated amine-porphyrin hybrids, retaining their full catalytic activity, can be recovered in high yield.MDPI2021202120202021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/175864Articles 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/10.3390/molecules25153420Molecules, 2020, vol. 25, num. 15https://doi.org/10.3390/molecules25153420cc-by (c) Arlegui Chamizo, Aitor et al., 2020http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:recercat.cat:2445/1758642026-05-29T05:05:01Z
dc.title.none.fl_str_mv Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
title Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
spellingShingle Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
Arlegui Chamizo, Aitor
Porfirines
Catàlisi
Reacció aldòlica
Porphyrins
Catalysis
Aldol reaction
title_short Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
title_full Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
title_fullStr Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
title_full_unstemmed Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
title_sort Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
dc.creator.none.fl_str_mv Arlegui Chamizo, Aitor
Torres, Pol
Cuesta Turienzo, Víctor
Crusats i Aliguer, Joaquim
Moyano i Baldoire, Albert
author Arlegui Chamizo, Aitor
author_facet Arlegui Chamizo, Aitor
Torres, Pol
Cuesta Turienzo, Víctor
Crusats i Aliguer, Joaquim
Moyano i Baldoire, Albert
author_role author
author2 Torres, Pol
Cuesta Turienzo, Víctor
Crusats i Aliguer, Joaquim
Moyano i Baldoire, Albert
author2_role author
author
author
author
dc.subject.none.fl_str_mv Porfirines
Catàlisi
Reacció aldòlica
Porphyrins
Catalysis
Aldol reaction
topic Porfirines
Catàlisi
Reacció aldòlica
Porphyrins
Catalysis
Aldol reaction
description Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take place, whereas under acidic conditions, the porphyrinic protonated core of the hybrid leads to the formation of self-assembled structures, so that the hybrids flocculate and their catalytic activity is fully suppressed. The low degree of chirality transfer observed for aqueous Michael and aldol reactions strongly suggests that these reactions take place under true "in water" organocatalytic conditions. The highly insoluble catalyst aggregates can easily be separated from the reaction products by centrifugation of the acidic reaction mixtures, and after neutralization and desalting, the sodium salts of the sulfonated amine-porphyrin hybrids, retaining their full catalytic activity, can be recovered in high yield.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
2021
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/2445/175864
url https://hdl.handle.net/2445/175864
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/10.3390/molecules25153420
Molecules, 2020, vol. 25, num. 15
https://doi.org/10.3390/molecules25153420
dc.rights.none.fl_str_mv cc-by (c) Arlegui Chamizo, Aitor et al., 2020
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Arlegui Chamizo, Aitor et al., 2020
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
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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score 15.812429

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