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Azafullerene C59N-phthalocyanine dyad: synthesis, characterisation and photoinduced electron transfer
- Source :
- Chemphyschem : a European journal of chemical physics and physical chemistry. 13(5)
- Publication Year :
- 2011
-
Abstract
- 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.
- Subjects :
- Quenching (fluorescence)
Absorption spectroscopy
010405 organic chemistry
Infrared spectroscopy
010402 general chemistry
Photochemistry
01 natural sciences
Atomic and Molecular Physics, and Optics
Photoinduced electron transfer
0104 chemical sciences
chemistry.chemical_compound
Electron transfer
Benzonitrile
chemistry
Phthalocyanine
Physical and Theoretical Chemistry
Spectroscopy
Subjects
Details
- ISSN :
- 14397641
- Volume :
- 13
- Issue :
- 5
- Database :
- OpenAIRE
- Journal :
- Chemphyschem : a European journal of chemical physics and physical chemistry
- Accession number :
- edsair.doi.dedup.....b50eb29e666c7c67f2540deeb98228d3