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Azafullerene C 59 N–Phthalocyanine Dyad: Synthesis, Characterisation and Photoinduced Electron Transfer
Author(s) -
Rotas Georgios,
Ranta Jenni,
Efimov Alexander,
Niemi Marja,
Lemmetyinen Helge,
Tkachenko Nikolai,
Tagmatarchis Nikos
Publication year - 2012
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201101029
Subject(s) - chemistry , spectroscopy , benzonitrile , photochemistry , excited state , quenching (fluorescence) , phthalocyanine , electron transfer , cyclic voltammetry , photoluminescence , electrochemistry , materials science , fluorescence , organic chemistry , electrode , physics , optoelectronics , quantum mechanics , nuclear physics
The synthesis of a new azafullerene C 59 N–phthalocyanine (Pc) dyad is described. The key step for the synthesis of the C 59 N–Pc dyad was the formation of the C 59 N‐based carboxylic acid, which was smoothly condensed with hydroxy‐modified Pc. The structure of the C 59 N–Pc dyad was verified by 1 H and 13 C NMR spectroscopy, IR spectroscopy, UV/Vis spectroscopy and MS measurements. The photophysical and electrochemical properties of the C 59 N–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 C 59 N–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 C 60 –Pc dyad, which revealed that the different excited‐state energies and reduction potentials of the two fullerene spheres (i.e. C 59 N vs. C 60 ) strongly diverged in the deactivation pathways of the excited states of the corresponding phthalocyanine dyads.