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Tuning the Activity-Stability Balance of Photocatalytic Organic Materials for Oxidative Coupling Reactions

Author
Jiménez Almarza, Aliciauntranslated; López Magano, Albertountranslated; Mas Ballesté, Rubénuntranslated; Alemán Lara, José Juliánuntranslated
Entity
UAM. Departamento de Química Inorgánica
Publisher
American Chemical Society
Date
2022-03-29
Citation
10.1021/acsami.2c01646
ACS Applied Materials & Interfaces 14 (2022): 16258–16268
 
 
 
ISSN
1944-8244 (print); 1944-8252 (electronic)
DOI
10.1021/acsami.2c01646
Funded by
Financial support was provided by the European Research Council (ERC-CoG, Contract No. 647550, ERC-PoC, Contract No. 861930), the Spanish Government (RTI2018- 095038−B-I00, PID2019-110637RB-I00), “Comunidad de Madrid”, and European Structural Funds (S2018/NMT4367) and proyectos sinérgicos I+D (Y2020/NMT-6469). A.L.-M. thanks Universidad Autónoma de Madrid for a predoctoral FPI-UAM fellowship
Project
Gobierno de España. RTI2018- 095038−B-I00
Editor's Version
https://doi.org/10.1021/acsami.2c01646
Subjects
amines; imines; organic materials; oxidative coupling; photocatalysis; Química
URI
http://hdl.handle.net/10486/703046
Rights
© 2022 The Authors

Licencia Creative Commons
Esta obra está bajo una Licencia Creative Commons Atribución 4.0 Internacional.

Abstract

Three materials containing a photoactive unit, 10-phenyl phenothiazine (PTH), have been studied for the visible light-mediated oxidative coupling of amines. In particular, the materials considered are assembled through the condensation of extended polyimine, polyhydrazone, or polytriazine frameworks. These three materials present different stabilities in the presence of strong nucleophiles such as amines, which is a key factor for efficient catalytic performance. In the series of materials reported herein, the triazine-based material shows the optimal compromise between activity and stability when studied for the oxidative coupling of amines, achieving imine products. Accordingly, while significant leaching of molecular active fragments is ruled out for triazine-based polymers, other materials of the series show a significant chemical erosion as a result of the reaction with the amine substrates. Consequently, only a triazine-based material allows performing several catalytic cycles (up to seven) with yields higher than 80%. The applicability of this heterogeneous catalyst has been proven with a variety of substrates, confirming its stability and obtaining diverse imine coupling products with excellent yields
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Google™ Scholar:Jiménez Almarza, Alicia - López Magano, Alberto - Mas Ballesté, Rubén - Alemán Lara, José Julián

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  • Producción científica en acceso abierto de la UAM [18125]

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