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Formyl-Porphyrin and Formyl-Fullerenoporphyrin Building Blocks for the Construction of Multiporphyrin Arrays

Authors

  • Maxence Urbani,

    1. Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France
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  • Julien Iehl,

    1. Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France
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  • Iwona Osinska,

    1. Groupe de Radiocristallographie, Institut de Chimie, CNRS et Université de Strasbourg, 1 rue Blaise Pascal, B. P. 296R8, 67008 Strasbourg Cedex, France
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  • Rémy Louis,

    1. Groupe de Radiocristallographie, Institut de Chimie, CNRS et Université de Strasbourg, 1 rue Blaise Pascal, B. P. 296R8, 67008 Strasbourg Cedex, France
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  • Michel Holler,

    1. Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France
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  • Jean-François Nierengarten

    1. Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France
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Abstract

A fullerene derivative bearing a benzaldehyde unit has been prepared and used as starting material for the synthesis of a formyl-fullerenoporphyrin building block. Condensation of this aldehyde with pyrrole in CHCl3 with BF3·Et2O as catalyst followed by p-chloranil oxidation yielded a pentaporphyrinic scaffold surrounded by four peripheral C60 subunits. By following a similar strategy, a bis-porphyrin building block bearing an aldehyde function was prepared and used for the construction of a nonaporphyrin array by reaction with pyrrole under typical porphyrin synthesis conditions. Whereas the 1H NMR spectrum recorded at room temperature for the nonaporphyrin system is well defined, the signals recorded under the same conditions for the pentaporphyrin derivative surrounded by four peripheral C60 groups are broad. Indeed, the C60-pentaporphyrin ensemble appears as a mixture of conformers which equilibrate slowly on the NMR time scale at room temperature.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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