Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives
In this article, we present experimental and theoretical studies of pyridine derivatives (pyDs) inspired by natural systems to investigate the electron transfer processes occurring in aqueous media and elaborate a theoretical model that adequately predicts the behavior of new derivatives. Our result...
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2025-06-01
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| author | Gloria M. Acosta-Tejada Martha M. Flores-Leonar Jazmín García-Ramírez Víctor M. Ugalde-Saldívar Alfredo Vázquez |
| author_facet | Gloria M. Acosta-Tejada Martha M. Flores-Leonar Jazmín García-Ramírez Víctor M. Ugalde-Saldívar Alfredo Vázquez |
| author_sort | Gloria M. Acosta-Tejada |
| collection | DOAJ |
| description | In this article, we present experimental and theoretical studies of pyridine derivatives (pyDs) inspired by natural systems to investigate the electron transfer processes occurring in aqueous media and elaborate a theoretical model that adequately predicts the behavior of new derivatives. Our results might be relevant to scientific and technological applications, including energy storage, redox-active scaffolds for organic synthesis, photoredox catalysis, and new materials. The synthesis of eight pyDs is reported. To improve water solubility, six new compounds are hexafluorophosphate alkylammonium salts. The pyDs exhibit irreversible redox processes, with electron-donating substituents decreasing the cathodic peak potential while electron-withdrawing groups increase it; when both substituents are present, the latter effect prevails. A computational study was performed to investigate the electrochemical behavior of the synthesized compounds and design new electroactive pyDs. DFT calculations provided the predominant species’ redox potentials and acidity constants to elaborate Pourbaix diagrams for each compound. The synthesized molecules exhibit a two-electron-one-proton dismutation process in the water pH window. Beyond this range, stabilized radical species undergo one-electron exchange processes. We correlated experimental and calculated parameters, screening 22 additional derivatives to evaluate their electrochemical behavior, identifying potential candidates capable of performing a one-electron transfer process in the pH window of water, revealing new applications for pyDs. |
| format | Article |
| id | doaj-art-e066f07600404a05b2d91c94349af0ba |
| institution | Kabale University |
| issn | 2624-8549 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
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| series | Chemistry |
| spelling | doaj-art-e066f07600404a05b2d91c94349af0ba2025-08-20T03:27:18ZengMDPI AGChemistry2624-85492025-06-017310010.3390/chemistry7030100Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine DerivativesGloria M. Acosta-Tejada0Martha M. Flores-Leonar1Jazmín García-Ramírez2Víctor M. Ugalde-Saldívar3Alfredo Vázquez4Facultad de Química, Universidad Nacional Autónoma de México, Coyoacán, Cd. Universitaria, Mexico City 04510, MexicoFacultad de Química, Universidad Nacional Autónoma de México, Coyoacán, Cd. Universitaria, Mexico City 04510, MexicoFacultad de Química, Universidad Nacional Autónoma de México, Coyoacán, Cd. Universitaria, Mexico City 04510, MexicoFacultad de Química, Universidad Nacional Autónoma de México, Coyoacán, Cd. Universitaria, Mexico City 04510, MexicoFacultad de Química, Universidad Nacional Autónoma de México, Coyoacán, Cd. Universitaria, Mexico City 04510, MexicoIn this article, we present experimental and theoretical studies of pyridine derivatives (pyDs) inspired by natural systems to investigate the electron transfer processes occurring in aqueous media and elaborate a theoretical model that adequately predicts the behavior of new derivatives. Our results might be relevant to scientific and technological applications, including energy storage, redox-active scaffolds for organic synthesis, photoredox catalysis, and new materials. The synthesis of eight pyDs is reported. To improve water solubility, six new compounds are hexafluorophosphate alkylammonium salts. The pyDs exhibit irreversible redox processes, with electron-donating substituents decreasing the cathodic peak potential while electron-withdrawing groups increase it; when both substituents are present, the latter effect prevails. A computational study was performed to investigate the electrochemical behavior of the synthesized compounds and design new electroactive pyDs. DFT calculations provided the predominant species’ redox potentials and acidity constants to elaborate Pourbaix diagrams for each compound. The synthesized molecules exhibit a two-electron-one-proton dismutation process in the water pH window. Beyond this range, stabilized radical species undergo one-electron exchange processes. We correlated experimental and calculated parameters, screening 22 additional derivatives to evaluate their electrochemical behavior, identifying potential candidates capable of performing a one-electron transfer process in the pH window of water, revealing new applications for pyDs.https://www.mdpi.com/2624-8549/7/3/100alkylation of pyridineswater soluble pyridinescyclic voltamperometryredox propertiesdensity functional calculationsPourbaix diagram |
| spellingShingle | Gloria M. Acosta-Tejada Martha M. Flores-Leonar Jazmín García-Ramírez Víctor M. Ugalde-Saldívar Alfredo Vázquez Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives Chemistry alkylation of pyridines water soluble pyridines cyclic voltamperometry redox properties density functional calculations Pourbaix diagram |
| title | Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives |
| title_full | Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives |
| title_fullStr | Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives |
| title_full_unstemmed | Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives |
| title_short | Nature-Inspired Redox Active Organic Molecules: Design, Synthesis, and Characterization of Pyridine Derivatives |
| title_sort | nature inspired redox active organic molecules design synthesis and characterization of pyridine derivatives |
| topic | alkylation of pyridines water soluble pyridines cyclic voltamperometry redox properties density functional calculations Pourbaix diagram |
| url | https://www.mdpi.com/2624-8549/7/3/100 |
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