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Synthesis of Fullerodendrons with an Ammonium Unit at the Focal Point and Their Cooperative Self‐Assembly on a Fluorescent Ditopic Crown Ether Receptor
Author(s) -
Nierengarten JeanFrançois,
Hahn Uwe,
Trabolsi Ali,
Herschbach Haiko,
Cardinali François,
Elhabiri Mourad,
Leize Emmanuelle,
Van Dorsselaer Alain,
AlbrechtGary AnneMarie
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.200501238
Subject(s) - supramolecular chemistry , crown ether , fullerene , fluorescence , intramolecular force , titration , chemistry , receptor , self assembly , crystallography , stereochemistry , organic chemistry , ion , crystal structure , biochemistry , physics , quantum mechanics
Dendritic branches with 1, 2, or 4 peripheral fullerene subunits and an ammonium function at the focal point have been prepared. Their ability to form self‐assembled dendritic structures with oligophenylenevinylene receptors bearing one or two crown ether moieties has been evidenced by ES‐MS studies for the first time. These supramolecular complexes are multicomponent photoactive devices in which the emission of the central receptor is dramatically quenched by the fullerene units. This new property resulting from the association of the different molecular subunits allowed detailed investigations of the self‐assembly process by means of fluorescence titrations. The binding studies have revealed positive cooperative effects for the assembly of the fullerodendrimers with the ditopic receptor. Interestingly, the stability of the supramolecular 2:1 structures increases as the size of the dendritic unit increases. This positive dendritic effect has been explained by the larger number of possible intramolecular fullerene–fullerene interactions between the two dendritic guests when the number of fullerene subunits is increased.