Bioinspired Functional Catechol Derivatives through Simple Thiol Conjugate Addition |
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Authors: | Dr. Juan Mancebo-Aracil Carolina Casagualda Miguel Ángel Moreno-Villaécija Dr. Fabiana Nador Dr. Javier García-Pardo Dr. Antonio Franconetti-García Dr. Félix Busqué Dr. Ramon Alibés Dr. María José Esplandiu Dr. Daniel Ruiz-Molina Dr. Josep Sedó-Vegara |
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Affiliation: | 1. Catalan Institute of Nanoscience and Nanotechnology (ICN2), CSIC and BIST, Campus de la UAB, 08193 Bellaterra, Spain;2. Departament de Química, Universitat Autònoma de Barcelona (UAB), Campus de la UAB, 08193 Bellaterra, Spain;3. Instituto de Química del Sur-INQUISUR (UNS-CONICET), Universidad Nacional del Sur, Av. Alem 1253, 8000 Bahía Blanca, Buenos Aires, Argentina |
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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. |
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Keywords: | bioinspired materials catechols functional coatings sulfur surfaces and interfaces theranostics thiol conjugate addition |
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