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Comparison between the Photophysical Properties of Pyrazolo‐ and Isoxazolo[60]fullerenes with Dual Donors (Ferrocene, Aniline and Alkoxyphenyl)
Author(s) -
Perez Laura,
ElKhouly Mohamed E.,
de la Cruz Pilar,
Araki Yasuyuki,
Ito Osamu,
Langa Fernando
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600921
Subject(s) - chemistry , pyrazoline , ferrocene , fullerene , aniline , ring (chemistry) , photochemistry , benzoquinone , excited state , covalent bond , singlet oxygen , medicinal chemistry , oxygen , organic chemistry , electrochemistry , electrode , nuclear physics , physics
Abstract Two series of new pyrazolo‐ and isoxazolo[60]fullerenes covalently linked to vinylenephenylene bearing ferrocene, dibutylaniline or dodecyloxyphenyl electron‐donor groups attached in the periphery have been synthesized. The photophysical properties of these newly synthesized dual‐donor–C 60 derivatives have been investigated and compared by applying time‐resolved fluorescence and nanosecond transient techniques in both polar and nonpolar solvents. Charge separation via the excited singlet state of C 60 is more efficient in the pyrazolo‐C 60 triads than in the isoxazolo‐C 60 triads. It was found that the pyrazoline ring mediates charge separation as a result of the stronger electron‐donating character of the nitrogen atom of the pyrazoline ring compared with the oxygen atom of the isoxazoline ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)