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Supramolecular complexes obtained from porphyrin-crown ether conjugates and a fullerene derivative bearing an ammonium unit |
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| Authors: | Nathalie Solladié Mathieu E Walther Emmanuelle Leize Teresa M Figueira Duarte |
| Institution: | a Groupe de Synthèse de Systèmes Porphyriniques, Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France b Laboratoire de Spectrométrie de Masse Bio-organique, Ecole de Chimie, Polymères et Matériaux (ECPM), Université Louis Pasteur and CNRS, 25 rue Becquerel, 67087 Strasbourg Cedex 2, France c Groupe de Chimie des Fullerènes et des Systèmes Conjugués, Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France |
| Abstract: | A methanofullerene derivative with an ammonium subunit (1) has been prepared and its ability to form a supramolecular complex with a porphyrin-crown ether conjugate evidenced by NMR, UV-vis, electrospray mass spectrometry (ES-MS) and luminescence experiments. Interestingly, in addition to the ammonium-crown ether recognition, intramolecular stacking of the fullerene moiety and the porphyrin subunit has been evidenced. Due to this additional recognition element, the association constant for the supramolecular complex is increased by two orders of magnitude when compared to the Ka values found for the complexation of 1 with benzo-18-crown-6. Finally, non-covalent systems resulting from the association of cation 1 with porphyrin derivatives bearing two crown ether subunits have been investigated. Intramolecular C60-porphyrin interactions have also been evidenced within these supramolecular complexes. As a result, the 2:1 complexes are very stable as shown by the ES-MS studies. |
| Keywords: | Binding studies Crown ether Fullerene Porphyrin Supramolecular chemistry |
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