Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition

Mancebo Aracil, Juan|||0000-0003-2627-9161; Casagualda Clapés, Carolina|||0000-0002-6160-6730; Moreno Villaécija, Miguel Ángel|||0000-0003-2410-0682; Nador, Fabiana|||0000-0003-2502-0430; Garcia-Pardo, Javier|||0000-0001-9179-6371; Franconetti, Antonio|||0000-0002-7972-8795; Busqué, Félix|||0000-0001-7566-4264; Alibés, Ramon|||0000-0002-7997-2691; Esplandiu Egido, Maria José|||0000-0003-2079-0639; Ruiz-Molina, Daniel|||0000-0002-6844-8421; Sedó Vegara, Josep|||0000-0002-4195-7541

Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition

The combination of the surface-adhesive properties of catechol rings and functional moieties conveying specific properties is very appealing to materials chemistry, but the preparation of catechol derivatives often requires elaborate synthetic routes to circumvent the intrinsic reactivity of the cat...

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Autores:	Mancebo Aracil, Juan\|\|\|0000-0003-2627-9161, Casagualda Clapés, Carolina\|\|\|0000-0002-6160-6730, Moreno Villaécija, Miguel Ángel\|\|\|0000-0003-2410-0682, Nador, Fabiana\|\|\|0000-0003-2502-0430, Garcia-Pardo, Javier\|\|\|0000-0001-9179-6371, Franconetti, Antonio\|\|\|0000-0002-7972-8795, Busqué, Félix\|\|\|0000-0001-7566-4264, Alibés, Ramon\|\|\|0000-0002-7997-2691, Esplandiu Egido, Maria José\|\|\|0000-0003-2079-0639, Ruiz-Molina, Daniel\|\|\|0000-0002-6844-8421, Sedó Vegara, Josep\|\|\|0000-0002-4195-7541
Tipo de recurso:	artículo
Fecha de publicación:	2019
País:	España
Institución:	Universitat Autònoma de Barcelona
Repositorio:	Dipòsit Digital de Documents de la UAB
Idioma:	inglés
OAI Identifier:	oai:ddd.uab.cat:220666
Acceso en línea:	https://ddd.uab.cat/record/220666 https://dx.doi.org/urn:doi:10.1002/chem.201901914
Access Level:	acceso abierto
Palabra clave:	Bioinspired materials Catechols Functional coatings Sulfur Surfaces and interfaces Theranostics Thiol conjugate addition

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spelling	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate AdditionMancebo Aracil, Juan\|\|\|0000-0003-2627-9161Casagualda Clapés, Carolina\|\|\|0000-0002-6160-6730Moreno Villaécija, Miguel Ángel\|\|\|0000-0003-2410-0682Nador, Fabiana\|\|\|0000-0003-2502-0430Garcia-Pardo, Javier\|\|\|0000-0001-9179-6371Franconetti, Antonio\|\|\|0000-0002-7972-8795Busqué, Félix\|\|\|0000-0001-7566-4264Alibés, Ramon\|\|\|0000-0002-7997-2691Esplandiu Egido, Maria José\|\|\|0000-0003-2079-0639Ruiz-Molina, Daniel\|\|\|0000-0002-6844-8421Sedó Vegara, Josep\|\|\|0000-0002-4195-7541Bioinspired materialsCatecholsFunctional coatingsSulfurSurfaces and interfacesTheranosticsThiol conjugate additionThe combination of the surface-adhesive properties of catechol rings and functional moieties conveying specific properties is very appealing to materials chemistry, but the preparation of catechol derivatives often requires elaborate synthetic routes to circumvent the intrinsic reactivity of the catechol ring. In this work, functional catechols are synthesized straightforwardly by using the bioinspired reaction of several functional thiols with o-benzoquinone. With one exception, the conjugated addition of the thiol takes place regioselectively at the 3-position of the quinone, and is rationalized by DFT calculations. Overall, this synthetic methodology provides a general and straightforward access to functional and chain-extended catechol derivatives, which are later tested with regard to their hydro-/oleophobicity, colloidal stability, fluorescence, and metal-coordinating capabilities in proof-of-concept applications. 22019-01-0120192019-01-01Articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/220666https://dx.doi.org/urn:doi:10.1002/chem.201901914reponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengMinisterio de Economía y Competitividad https://doi.org/10.13039/501100003329 FPU-2015-03245Ministerio de Economía y Competitividad https://doi.org/10.13039/501100003329 SEV-2013-0295Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CTQ2016-75363-RMinisterio de Economía y Competitividad https://doi.org/10.13039/501100003329 MAT2015-70615-Ropen accesshttp://purl.org/coar/access_right/c_abf2Aquest material està protegit per drets d'autor i/o drets afins. Podeu utilitzar aquest material en funció del que permet la legislació de drets d'autor i drets afins d'aplicació al vostre cas. Per a d'altres usos heu d'obtenir permís del(s) titular(s) de drets.https://rightsstatements.org/vocab/InC/1.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:2206662026-06-06T12:50:31Z
dc.title.none.fl_str_mv	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
title	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
spellingShingle	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition Mancebo Aracil, Juan\|\|\|0000-0003-2627-9161 Bioinspired materials Catechols Functional coatings Sulfur Surfaces and interfaces Theranostics Thiol conjugate addition
title_short	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
title_full	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
title_fullStr	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
title_full_unstemmed	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
title_sort	Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
dc.creator.none.fl_str_mv	Mancebo Aracil, Juan\|\|\|0000-0003-2627-9161 Casagualda Clapés, Carolina\|\|\|0000-0002-6160-6730 Moreno Villaécija, Miguel Ángel\|\|\|0000-0003-2410-0682 Nador, Fabiana\|\|\|0000-0003-2502-0430 Garcia-Pardo, Javier\|\|\|0000-0001-9179-6371 Franconetti, Antonio\|\|\|0000-0002-7972-8795 Busqué, Félix\|\|\|0000-0001-7566-4264 Alibés, Ramon\|\|\|0000-0002-7997-2691 Esplandiu Egido, Maria José\|\|\|0000-0003-2079-0639 Ruiz-Molina, Daniel\|\|\|0000-0002-6844-8421 Sedó Vegara, Josep\|\|\|0000-0002-4195-7541
author	Mancebo Aracil, Juan\|\|\|0000-0003-2627-9161
author_facet	Mancebo Aracil, Juan\|\|\|0000-0003-2627-9161 Casagualda Clapés, Carolina\|\|\|0000-0002-6160-6730 Moreno Villaécija, Miguel Ángel\|\|\|0000-0003-2410-0682 Nador, Fabiana\|\|\|0000-0003-2502-0430 Garcia-Pardo, Javier\|\|\|0000-0001-9179-6371 Franconetti, Antonio\|\|\|0000-0002-7972-8795 Busqué, Félix\|\|\|0000-0001-7566-4264 Alibés, Ramon\|\|\|0000-0002-7997-2691 Esplandiu Egido, Maria José\|\|\|0000-0003-2079-0639 Ruiz-Molina, Daniel\|\|\|0000-0002-6844-8421 Sedó Vegara, Josep\|\|\|0000-0002-4195-7541
author_role	author
author2	Casagualda Clapés, Carolina\|\|\|0000-0002-6160-6730 Moreno Villaécija, Miguel Ángel\|\|\|0000-0003-2410-0682 Nador, Fabiana\|\|\|0000-0003-2502-0430 Garcia-Pardo, Javier\|\|\|0000-0001-9179-6371 Franconetti, Antonio\|\|\|0000-0002-7972-8795 Busqué, Félix\|\|\|0000-0001-7566-4264 Alibés, Ramon\|\|\|0000-0002-7997-2691 Esplandiu Egido, Maria José\|\|\|0000-0003-2079-0639 Ruiz-Molina, Daniel\|\|\|0000-0002-6844-8421 Sedó Vegara, Josep\|\|\|0000-0002-4195-7541
author2_role	author author author author author author author author author author
dc.subject.none.fl_str_mv	Bioinspired materials Catechols Functional coatings Sulfur Surfaces and interfaces Theranostics Thiol conjugate addition
topic	Bioinspired materials Catechols Functional coatings Sulfur Surfaces and interfaces Theranostics Thiol conjugate addition
description	The combination of the surface-adhesive properties of catechol rings and functional moieties conveying specific properties is very appealing to materials chemistry, but the preparation of catechol derivatives often requires elaborate synthetic routes to circumvent the intrinsic reactivity of the catechol ring. In this work, functional catechols are synthesized straightforwardly by using the bioinspired reaction of several functional thiols with o-benzoquinone. With one exception, the conjugated addition of the thiol takes place regioselectively at the 3-position of the quinone, and is rationalized by DFT calculations. Overall, this synthetic methodology provides a general and straightforward access to functional and chain-extended catechol derivatives, which are later tested with regard to their hydro-/oleophobicity, colloidal stability, fluorescence, and metal-coordinating capabilities in proof-of-concept applications.
publishDate	2019
dc.date.none.fl_str_mv	2 2019-01-01 2019 2019-01-01
dc.type.none.fl_str_mv	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://ddd.uab.cat/record/220666 https://dx.doi.org/urn:doi:10.1002/chem.201901914
url	https://ddd.uab.cat/record/220666 https://dx.doi.org/urn:doi:10.1002/chem.201901914
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 https://doi.org/10.13039/501100003329 FPU-2015-03245 Ministerio de Economía y Competitividad https://doi.org/10.13039/501100003329 SEV-2013-0295 Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CTQ2016-75363-R Ministerio de Economía y Competitividad https://doi.org/10.13039/501100003329 MAT2015-70615-R
dc.rights.none.fl_str_mv	open access http://purl.org/coar/access_right/c_abf2 https://rightsstatements.org/vocab/InC/1.0/
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 https://rightsstatements.org/vocab/InC/1.0/
eu_rights_str_mv	openAccess
dc.format.none.fl_str_mv	application/pdf
dc.source.none.fl_str_mv	reponame:Dipòsit Digital de Documents de la UAB instname:Universitat Autònoma de Barcelona
instname_str	Universitat Autònoma de Barcelona
reponame_str	Dipòsit Digital de Documents de la UAB
collection	Dipòsit Digital de Documents de la UAB
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repository.mail.fl_str_mv
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Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition

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