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Monomeric Azaheterofullerene Derivatives RC 59 N: Influence of the R Moiety on Spectroscopic and Photophysical Properties
Author(s) -
Hauke Frank,
Vostrowsky Otto,
Hirsch Andreas,
Quaranta Annamaria,
Leibl Winfried,
Leach Sydney,
Edge Ruth,
Navaratnam Suppiah,
Bensasson René V.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501536
Subject(s) - moiety , chemistry , photochemistry , singlet state , triplet state , excited state , monomer , absorption spectroscopy , quantum yield , absorption (acoustics) , fluorescence , ring (chemistry) , singlet oxygen , molecule , oxygen , materials science , stereochemistry , organic chemistry , physics , quantum mechanics , nuclear physics , composite material , polymer
We have synthesised nine monomeric azaheterofullerene (AZA) derivatives, RC 59 N, with a wide variety of different side chains R and investigated their spectroscopic and photophysical properties in toluene and o ‐dichlorobenzene (ODCB). Measurements include their ground‐state absorption spectra, molar absorption coefficient ( ε G ), fluorescence spectra, fluorescence quantum yields ( Φ F ), singlet‐state lifetimes ( τ F ), triplet‐state absorption spectra, triplet molar absorption coefficients ( ε T ), singlet oxygen ( Φ Δ ), and triplet state ( Φ T ) quantum yields. The replacement of a carbon by a nitrogen atom in the C 60 sphere strongly affects most of the spectroscopic and photophysical properties. The chemical nature of the R moiety has definite effects on these properties in contrast with minor effects on the chemical nature of the addends in [6,6]‐ring bridged monoadduct methano[60]fullerene derivatives. These effects concern properties of the ground state, singlet excited state, and triplet states of our nine RC 59 N derivatives and in particular the values of photophysical parameters ε G , ε T , Φ Δ , and Φ T , which are significantly lower than those of analogous monoadduct [6,6]‐ring bridged methano[60]fullerene derivatives.