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Efficient Greenish Blue Electrochemiluminescence from Fluorene and Spirobifluorene Derivatives

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    Efficient Greenish Blue Electrochemiluminescence from Fluorene and Spirobifluorene Derivatives
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    † Physikalisches Institut, Westfälische Wilhelms-Universität, Heisenbergstrasse 11, D-48149 Münster, Germany
    ‡ Istituto di Scienze e Tecnologie Molecolari (ISTM), CNR, Via Golgi 19, I-20133 Milano, Italy
    § Polo Scientifico Tecnologico (PST), CNR, Via Fantoli 16/15, I-20138 Milano, Italy
    [email protected]; [email protected]
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    Cite this: J. Am. Chem. Soc. 2012, 134, 37, 15402–15409
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    https://doi.org/10.1021/ja3054018
    Published August 9, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    The spectroscopic and electrochemical behavior as well as electrogenerated chemiluminescence (ECL) of a series of donor−π–donor derivatives bearing triphenylamine groups as donor connected to a fluorene, 2,7-bis-(4-(N,N-diphenylamino)phen-1-yl)-9,9′-dimethylfluorene (1), or spirobifluorene core, 2,7-bis-(4-(N,N-diphenylamino)phen-1-yl)-9,9′-spirobifluorene (2) and 2,2′,7,7′-tetrakis(4-(N,N-diphenylamino)phen-1-yl)-9,9′-spirobifluorene (3), were investigated. Besides a high photoluminescence (PL) quantum yield in solution (between 81 and 87%), an efficient radical ions annihilation process induces intense greenish blue ECL emission that could be seen with the naked eye. Only the tetrasubstituted spirobifluorene derivative (compound 3) shows weak ECL obtained by a direct annihilation mechanism. Because the energy of the annihilation reaction is higher than the energy required to form the singlet excited state, the S-route could be considered the pathway followed by the ECL process in these molecules. The ECL emissions recorded by direct ion–ion annihilation show two bands compared to the single structureless PL band. The ECL spectra obtained by a coreactant approach using benzoylperoxide as a coreagent show no differences relative to that produced by annihilation, except for an increasing of ECL intensity for all compounds.

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    Detailed synthetic procedure for all compounds; ECL photocurrent of 2; coreactant ECL emission of 3; and PL spectra of 2 in highly concentrated solution excited at different wavelengths. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2012, 134, 37, 15402–15409
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