{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,13]],"date-time":"2026-03-13T01:07:36Z","timestamp":1773364056650,"version":"3.50.1"},"reference-count":50,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2022,10,8]],"date-time":"2022-10-08T00:00:00Z","timestamp":1665187200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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) \u2192 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.<\/jats:p>","DOI":"10.3390\/molecules27196690","type":"journal-article","created":{"date-parts":[[2022,10,9]],"date-time":"2022-10-09T23:31:43Z","timestamp":1665358303000},"page":"6690","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis, Electrochemical and Fluorescence Properties of the First Fluorescent Member of the Ferrocifen Family and of Its Oxidized Derivatives"],"prefix":"10.3390","volume":"27","author":[{"given":"Charles","family":"Fayolle","sequence":"first","affiliation":[{"name":"PASTEUR, D\u00e9partement de chimie, \u00c9cole Normale Sup\u00e9rieure, PSL University, Sorbonne Universit\u00e9 CNRS, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5374-5346","authenticated-orcid":false,"given":"Pascal","family":"Pigeon","sequence":"additional","affiliation":[{"name":"Institut Parisien de Chimie Mol\u00e9culaire (IPCM), CNRS, Sorbonne Universit\u00e9, 75005 Paris, France"},{"name":"ENSCP Chimie ParisTech, PSL University, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4715-5662","authenticated-orcid":false,"given":"Nathalie","family":"Fischer-Durand","sequence":"additional","affiliation":[{"name":"Institut Parisien de Chimie Mol\u00e9culaire (IPCM), CNRS, Sorbonne Universit\u00e9, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3039-5659","authenticated-orcid":false,"given":"Mich\u00e8le","family":"Salmain","sequence":"additional","affiliation":[{"name":"Institut Parisien de Chimie Mol\u00e9culaire (IPCM), CNRS, Sorbonne Universit\u00e9, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5452-1942","authenticated-orcid":false,"given":"Olivier","family":"Buriez","sequence":"additional","affiliation":[{"name":"PASTEUR, D\u00e9partement de chimie, \u00c9cole Normale Sup\u00e9rieure, PSL University, Sorbonne Universit\u00e9 CNRS, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4044-2730","authenticated-orcid":false,"given":"Anne","family":"Vessi\u00e8res","sequence":"additional","affiliation":[{"name":"Institut Parisien de Chimie Mol\u00e9culaire (IPCM), CNRS, Sorbonne Universit\u00e9, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1905-7667","authenticated-orcid":false,"given":"Eric","family":"Labb\u00e9","sequence":"additional","affiliation":[{"name":"PASTEUR, D\u00e9partement de chimie, \u00c9cole Normale Sup\u00e9rieure, PSL University, Sorbonne Universit\u00e9 CNRS, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1016\/j.jconrel.2016.02.022","article-title":"Fluorescence optical imaging in anticancer drug delivery","volume":"226","author":"Etrych","year":"2016","journal-title":"J. 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