Academic Journal
Synthesis, Electrochemical and Fluorescence Properties of the First Fluorescent Member of the Ferrocifen Family and of Its Oxidized Derivatives
| Title: | Synthesis, Electrochemical and Fluorescence Properties of the First Fluorescent Member of the Ferrocifen Family and of Its Oxidized Derivatives |
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| Authors: | Charles Fayolle, Pascal Pigeon, Nathalie Fischer-Durand, Michèle Salmain, Olivier Buriez, Anne Vessières, Eric Labbé |
| Source: | Molecules, Vol 27, Iss 19, p 6690 (2022) |
| Publisher Information: | MDPI AG, 2022. |
| Publication Year: | 2022 |
| Collection: | LCC:Organic chemistry |
| Subject Terms: | ferrocene, coumarin, fluorescence switching, PET, redox state, Organic chemistry, QD241-441 |
| More Details: | The first fluorescent ferrociphenol derivative (P797) has been synthesized via McMurry cross-coupling followed by copper-catalyzed [3 + 2] azide-alkyne cycloaddition of the fluorescent group coumarin. Cyclic voltammograms of P797 exhibit either a monoelectronic oxidation wave ascribed to the ferrocene Fe(II) → Fe(III) conversion or a three-electron oxidation process in the presence of a base, leading to a Fe(III) quinone methide adduct. This general sequence is consistent with those previously described for non-fluorescent ferrociphenols. Furthermore, the fluorescence properties of P797 and its oxidized intermediates appear to strongly depend on the redox state of the ferrocene group. Indeed, electrochemical generation of Fe(III) (ferrocenium) states markedly increases the fluorescence emission intensity. In contrast, the emission of the Fe(II) (ferrocene) states is partially quenched by photoinduced electron transfer (PET) from the Fe(II) donor to the coumarin acceptor and by concentration-dependent self-quenching. Owing to its switchable fluorescence properties, complex P797 could represent an innovative and useful tool to study the biodistribution and the redox state of ferrocifens in cancer cells. |
| Document Type: | article |
| File Description: | electronic resource |
| Language: | English |
| ISSN: | 27196690 1420-3049 |
| Relation: | https://www.mdpi.com/1420-3049/27/19/6690; https://doaj.org/toc/1420-3049 |
| DOI: | 10.3390/molecules27196690 |
| Access URL: | https://doaj.org/article/3930e4c26eb648cd879c9a62fa1be0bf |
| Accession Number: | edsdoj.3930e4c26eb648cd879c9a62fa1be0bf |
| Database: | Directory of Open Access Journals |
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| ISSN: | 27196690 14203049 |
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| DOI: | 10.3390/molecules27196690 |
| Published in: | Molecules |
| Language: | English |