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Pyrene‐Based Dyad and Triad Leading to a Reversible Chemical and Redox Optical and Magnetic Switch
Author(s) -
Franco Carlos,
MasTorrent Marta,
Caballero Antonio,
Espinosa Arturo,
Molina Pedro,
Veciana Jaume,
Rovira Concepció
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405993
Subject(s) - radical , photochemistry , chemistry , triad (sociology) , pyrene , redox , moiety , intramolecular force , electrochemistry , diamagnetism , acceptor , quenching (fluorescence) , fluorescence , inorganic chemistry , stereochemistry , organic chemistry , magnetic field , psychology , physics , electrode , quantum mechanics , psychoanalysis , condensed matter physics
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.