Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
The synthesis of enantiomerically pure Ir(III) complexes with one or two BODIPY moieties has been achieved through the enantioselective C–H insertion from homochiral triazolium salts, containing a sulfoxide functionality in their structures. These homochiral salts were prepared by the sequential Cu-...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2020 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/229017 |
| Acceso en línea: | http://hdl.handle.net/10261/229017 |
| Access Level: | acceso abierto |
| Palabra clave: | Chirality Iridium BODIPYs Luminescence 7 MIC-ligands |
| Sumario: | The synthesis of enantiomerically pure Ir(III) complexes with one or two BODIPY moieties has been achieved through the enantioselective C–H insertion from homochiral triazolium salts, containing a sulfoxide functionality in their structures. These homochiral salts were prepared by the sequential Cu-catalyzed alkyne-azide cycloaddition (CuAAC) of an azide and one alkynyl sulfoxide, followed by a Suzuki coupling in the preformed triazole with a BODIPY containing aryl boronic acid, followed by methylation of the N3-triazole nitrogen. The configuration at the metal in these chiral complexes was established by using a combination of CD and X-ray diffraction techniques. The optical properties of these complexes were thoroughly studied using spectroscopic (absorption and fluorescence) and computational (TD-DFT and DFT) methods. The fluorescence of complexes with the BODIPY attached to the sulfoxide moiety (including the two BODIPYs-based complex) was quenched upon introduction of the Ir(III) fragment, most likely due to an a-PET mechanism. On the contrary, the fluorescence of Ir(III) complexes with the BODIPY attached to the triazolium ring remains unquenched. |
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