Pyrene-based dyad and triad leading to a reversible chemical and redox optical and magnetic switch

Carlos Franco, Marta Mas-Torrent, Antonio Caballero, Arturo Espinosa, Pedro Molina, Jaume Veciana, Concepciõ Rovira

    Research output: Contribution to journalArticleResearchpeer-review

    4 Citations (Scopus)

    Abstract

    © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Two new pyrene-polychlorotriphenylmethyl (PTM) dyads and triads have been synthesized and characterized by optical, magnetic, and electrochemical methods. The interplay between the different electronic states of the PTM moiety in the dyads and triads and the optical and magnetic properties of the molecules have been studied. The electronic spectra of the radicals 5. and 6. show the intramolecular charge-transfer transition at around 700 nm due to the acceptor character of the PTM radical. In the diamagnetic protonated derivatives 3 and 4 the fluorescence due to the pyrene is maintained, whereas in the radicals 5. and 6. and the corresponding anions 5- and 6- there is a clear quenching of the fluorescence, which is more efficient in the case of radicals. The redox activity of PTM radicals that are easily reduced to the corresponding carbanion has been exploited to fabricate electrochemical switches with optical and magnetic response. Switching properties: The synthesis of new pyrene-polychlorotriphenylmethyl (PTM) dyads and triads has permitted study of the interplay between the different electronic states of the PTM moiety and the optical and magnetic properties of the molecules, as well as their switching properties (see figure).
    Original languageEnglish
    Pages (from-to)5504-5509
    JournalChemistry - A European Journal
    Volume21
    Issue number14
    DOIs
    Publication statusPublished - 27 Mar 2015

    Keywords

    • donor-acceptor systems
    • electronic states
    • molecular devices
    • radicals
    • redox chemistry

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