2024-03-28T17:53:24Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/2001622020-10-14T08:51:22Zcom_10261_10252com_10261_3col_10261_10253
DIGITAL.CSIC
author
Mancebo-Aracil, Juan
author
Casagualda, Carolina
author
Moreno-Villaécija, Miguel Ángel
author
Nador, Fabiana
author
García-Pardo, Javier
author
Franconetti-García, Antonio
author
Busqué, Félix
author
Alibés, Ramón
author
Esplandiú, María J.
author
Ruiz Molina, Daniel
author
Sedó, Josep
funder
Ministerio de Economía y Competitividad (España)
funder
Ministerio de Ciencia e Innovación (España)
funder
European Commission
funder
Universidad Nacional del Sur
2020-02-10T13:00:23Z
2020-02-10T13:00:23Z
2019
Chemistry - A European Journal 25(53): 12367-12379 (2019)
0947-6539
http://hdl.handle.net/10261/200162
10.1002/chem.201901914
1521-3765
http://dx.doi.org/10.13039/501100003329http://dx.doi.org/10.13039/501100005740http://dx.doi.org/10.13039/501100000780http://dx.doi.org/10.13039/501100004837
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.
eng
openAccess
Bioinspired functional catechol derivatives through simple thiol conjugate addition
artículo
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URL
https://digital.csic.es/bitstream/10261/200162/3/bioinsaddit.pdf
File
MD5
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application/pdf
bioinsaddit.pdf