Azafullerene C59N–Phthalocyanine Dyad: Synthesis,Characterisation and Photoinduced Electron Transfer |
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| Authors: | Dr Georgios Rotas Dr Jenni Ranta Prof Alexander Efimov Dr Marja Niemi Prof Helge Lemmetyinen Prof Nikolai Tkachenko Prof Nikos Tagmatarchis |
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| Institution: | 1. Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation, 48 Vassileos Constantinou Avenue 11635 Athens (Greece), Fax: (+30)?210?7273794;2. Department of Chemistry and Bioengineering, Tampere University of Technology, P.O. Box 541, FIN‐33101 Tampere (Finland) |
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| Abstract: | The synthesis of a new azafullerene C59N–phthalocyanine (Pc) dyad is described. The key step for the synthesis of the C59N–Pc dyad was the formation of the C59N‐based carboxylic acid, which was smoothly condensed with hydroxy‐modified Pc. The structure of the C59N–Pc dyad was verified by 1H and 13C NMR spectroscopy, IR spectroscopy, UV/Vis spectroscopy and MS measurements. The photophysical and electrochemical properties of the C59N–Pc dyad were investigated in both polar and non‐polar solvents by steady state and time‐resolved photoluminescence and absorption spectroscopy, as well as by cyclic voltammetry. Different relaxation pathways for the photoexcited C59N–Pc dyad, as a result of changing the solvent polarity, were found, thus giving rise to energy‐transfer phenomena in non‐polar toluene and charge‐transfer processes in polar benzonitrile. Finally, the detailed quenching mechanisms were evaluated and compared with that of a C60–Pc dyad, which revealed that the different excited‐state energies and reduction potentials of the two fullerene spheres (i.e. C59N vs. C60) strongly diverged in the deactivation pathways of the excited states of the corresponding phthalocyanine dyads. |
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| Keywords: | electron transfer fullerenes photophysics phthalocyanines synthesis design |
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