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A Supramolecular Photosynthetic Model Made of a Multiporphyrinic Array Constructed around a C 60 Core and a C 60 –Imidazole Derivative
Author(s) -
Yoosaf K.,
Iehl Julien,
Nierengarten Iwona,
Hmadeh Mohamed,
AlbrechtGary AnneMarie,
Nierengarten JeanFrançois,
Armaroli Nicola
Publication year - 2014
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.201303481
Subject(s) - supramolecular chemistry , fullerene , intramolecular force , adduct , chemistry , benzonitrile , derivative (finance) , photochemistry , supramolecular assembly , binding constant , imidazole , quenching (fluorescence) , fluorescence , crystallography , stereochemistry , crystal structure , organic chemistry , binding site , biochemistry , physics , quantum mechanics , financial economics , economics
The photophysical properties of a supramolecular fullerene–porphyrin ensemble resulting from the self‐assembly of a pyrrolidinofullerene–imidazole derivative ( F1 ) with a multimetalloporphyrin array constructed around a hexasubstituted fullerene core ( F(ZnP) 12 ) have been investigated. The fullerene hexa‐adduct core of the host system does not play any active role in the cascade of photoinduced events of the supramolecular ensemble, indeed no intercomponent photoinduced processes could be observed in host F(ZnP) 12 . In contrast, upon axial coordination with the monosubstituted fullerene guest F1 , a quantitative quenching of the fluorescence signal of the metalloporphyrins was observed for the supramolecular complex [F(ZnP) 12 (F1) n ] both in polar and nonpolar solvents. In toluene, the supramolecular ensemble exhibits a charge transfer emission centered around 930 nm, suggesting the occurrence of intramolecular face‐to‐face interactions of F1 with neighboring metalloporphyrin moieties within the self‐assembled photoactive array. This mechanism is supported by the fact that a one order of magnitude increase in the binding constant was observed for the supramolecular complex [F(ZnP) 12 (F1) n ] when compared with a reference system lacking the pyrrolidinofullerene unit. In benzonitrile, a long‐lived charge‐separated state ( τ =0.3 μs) has been detected for the supramolecular adduct.