Azolium‐Porphyrin Electrosynthesis
Electrochemical oxidation of Zn(II) 2,7,12,17-tetra-tert-butylporphyrin in the presence of a series of azole derivatives (1-methylimidazole, 1-vinyl-1H-imidazole, 2-(1H-imidazol-1-yl)pyridine, 1-methylbenzimidazole, 1-methyl-1H-1,2,4-triazole, and benzothiazole) affords the corresponding meso-substituted azolium-porphyrins in very mild conditions and good yields. It was found that these nucleophiles were strongly ligated to the zinc(II) azolium-porphyrin complexes. Thus a demetalation/remetalation procedure was performed to recover the non-azole-coordinated zinc(II) complexes. X-ray crystallographic structures of three azolium-porphyrins were solved. Cyclic voltammetry analyses provided insight into the electron-withdrawing effect of the azolium substituents.
Authors
- Nesrine Amiri (ORCID: https://orcid.org/0000-0003-2102-2738)
- Sophie Fournier
- Fatima Akhssas
- Hélène Cattey
- Michal Trojan (ORCID: https://orcid.org/0000-0002-3894-1354)
- Charles H. Devillers (ORCID: https://orcid.org/0000-0001-9078-7035)
- Ludivine Poyac
- Emmanuel Lerayer (ORCID: https://orcid.org/0000-0001-9573-9497)
- Sébastien Richeter (ORCID: https://orcid.org/0000-0001-5284-0931)
- Sébastien Clément (ORCID: https://orcid.org/0000-0002-8473-8197)
- Thibault Ertel
- Rongning Lin
Institutions
- École Nationale Supérieure de Chimie de Montpellier (FR)
- Centre National de la Recherche Scientifique (FR)
- Université de Bourgogne (FR)
- Université de Montpellier (FR)
- Institut de Chimie (FR)
- Institut de Chimie Moléculaire de l'Université de Bourgogne (FR)
- University of Chemistry and Technology, Prague (CZ)
Publication Details
- Journal
- ChemSusChem
- Published
- 2024-08-22
- DOI
- https://doi.org/10.1002/cssc.202401439
- Citations
- 1
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.12
Funders
- Agence Nationale de la Recherche
- Université de Bourgogne
- Centre National de la Recherche Scientifique
- Conseil régional de Bourgogne-Franche-Comté
- European Regional Development Fund