Ferrocene functionalized enantiomerically pure Schiff bases and their Zn(ii ) and Pd(ii ) complexes: a spectroscopic, crystallographic, electrochemical and computational investigation
| Autor: | Salvador Celedón, Paul Hamon, Vania Artigas, Mauricio Fuentealba, Samia Kahlal, David Carrillo, Jean-Yves Saillard, Jean-René Hamon, Carolina Manzur |
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| Přispěvatelé: | Pontificia Universidad Católica de Valparaíso (PUCV), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fondo Nacional de Desarrollo Cientifico y Tecnologico (FONDECYT), Chile Comision Nacional de Investigacion Cientifica y Tecnologica (CONICYT) CONICYT FONDECYT [1090310], FONDEQUIP [EQM130154, EQM120095], Vicerrectoria de Investigacion y Estudios Avanzados, Pontificia Universidad Catolica de Valparaiso, Chile (VRIEA-PUCV), Centre National de la Recherche Scientifique (CNRS) Centre National de la Recherche Scientifique (CNRS), Universite de Rennes 1, VRIEAPUCV, FONDECYT Comision Nacional de Investigacion Cientifica y Tecnologica (CONICYT) CONICYT FONDECYT |
| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | New Journal of Chemistry New Journal of Chemistry, 2022, 46 (8), pp.3948-3960. ⟨10.1039/d1nj06106b⟩ |
| ISSN: | 1369-9261 1144-0546 |
| Popis: | International audience; In this contribution, we describe the synthesis, spectroscopic and structural characterization, as well as the electrochemical behavior of a series of four chiral ferrocene-functionalized Schiff base compounds derived from enantiomerically pure (1R,2R)-(-)-1,2-diaminocyclohexane. The ferrocene enaminones 3 and 4 were obtained upon monocondensation of ferrocenoylacetone Fc-C(= O)CH2C(QO)R (R = CH3, 1; 4-C6H4OH, 2; Fc = (eta(5)-C5H5)Fe(eta(5)-C5H4)) with one amino group of the primary diamine. The two bimetallic complexes 5 and 6 were prepared via a one-pot three-components template procedure involving half-unit 3, 4-methoxysalicylaldehyde and tetrahydrated zinc(II) nitrate for 5, and half-unit 4, 4-formyl-3-hydroxybenzoic acid and palladium(II) acetate for 6. All the syntheses were carried out in refluxing ethanol and compounds 3-6 were isolated as thermally stable, air and moisture compatible colored solids in 71-83% yields. They were characterized by several analytical (EA, ESI-MS) and spectroscopic methods (H-1/C-13 NMR, FT-IR, UV-vis), including the molecular structures of 3 and 4 that were unequivocally established by single crystal X-ray diffraction analyses. Both crystallize in the orthorhombic non-centrosymmetric space group P2(1)2(1)2(1) with two (R,R)-(-)-chiral carbon atoms in the structures. Cyclic voltammetry showed that the greatest anodic shifts (270 mV) of the ferrocenyl Fe(II)/Fe(III) redox potentials are observed for the D-pi-A push-pull derivative 6. Beyond experimental characterization, DFT- and TDDFT-based theoretical analyses of the new chiral ferrocene-containing Schiff base complexes allow interpretation of their observed spectroscopic, structural and electronic features. |
| Databáze: | OpenAIRE |
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