Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition
Mancebo Aracil, Juan (Institut Català de Nanociència i Nanotecnologia)
Casagualda Clapés, Carolina (Universitat Autònoma de Barcelona. Departament de Química)
Moreno Villaécija, Miguel Ángel (Institut Català de Nanociència i Nanotecnologia)
Nador, Fabiana (Universidad Nacional del Sur (Argentina))
Garcia-Pardo, Javier (Institut Català de Nanociència i Nanotecnologia)
Franconetti, Antonio (Universitat Autònoma de Barcelona. Departament de Química)
Busqué Sánchez, Félix (Universitat Autònoma de Barcelona. Departament de Química)
Alibes, Ramón (Universitat Autònoma de Barcelona. Departament de Química)
Esplandiu Egido, Maria José (Institut Català de Nanociència i Nanotecnologia)
Ruiz-Molina, Daniel (Institut Català de Nanociència i Nanotecnologia)
Sedó Vegara, Josep (Institut Català de Nanociència i Nanotecnologia)

Date:	2019
Abstract:	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.
Grants:	Ministerio de Economía y Competitividad FPU-2015-03245 Ministerio de Economía y Competitividad SEV-2013-0295 Agencia Estatal de Investigación CTQ2016-75363-R Ministerio de Economía y Competitividad MAT2015-70615-R
Rights:	Aquest 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.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Bioinspired materials ; Catechols ; Functional coatings ; Sulfur ; Surfaces and interfaces ; Theranostics ; Thiol conjugate addition
Published in:	Chemistry (Weinheim), Vol. 25, Issue 53 (September 2019) , p. 12367-12379, ISSN 1521-3765

DOI: 10.1002/chem.201901914
PMID: 31278780

Postprint 16 p, 1.2 MB

The record appears in these collections:
Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Synthesis of Bioactive Organic Compounds and Functional Materials (SynOrgFUN)
Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Catalan Institute of Nanoscience and Nanotechnology (ICN2)
Articles > Research articles
Articles > Published articles