Host–Guest Complexation of [60]Fullerenes and Porphyrins Enabled by “Click Chemistry”

Authors

  • Dr. Khanh-Hy Le Ho,

    1. IRAMIS, Laboratoire d'Electronique Moléculaire, SPEC (URA 2464), CEA-Saclay, 91191 Gif-sur-Yvette (France), Fax: (+33) 1-69-08-66-40
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  • Dr. Ismail Hijazi,

    1. IRAMIS, Laboratoire d'Electronique Moléculaire, SPEC (URA 2464), CEA-Saclay, 91191 Gif-sur-Yvette (France), Fax: (+33) 1-69-08-66-40
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  • Lucie Rivier,

    1. IRAMIS, Laboratoire d'Electronique Moléculaire, SPEC (URA 2464), CEA-Saclay, 91191 Gif-sur-Yvette (France), Fax: (+33) 1-69-08-66-40
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  • Dr. Christelle Gautier,

    1. IRAMIS, Laboratoire d'Electronique Moléculaire, SPEC (URA 2464), CEA-Saclay, 91191 Gif-sur-Yvette (France), Fax: (+33) 1-69-08-66-40
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  • Dr. Bruno Jousselme,

    1. IRAMIS, Laboratoire de Chimie des Surfaces et Interfaces, SPCSI, CEA-Saclay, 91191 Gif-sur-Yvette (France)
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  • Dr. Gustavo de Miguel,

    1. Department of Chemistry and Pharmacy and Interdisciplinary Center of Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany)
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  • Dr. Carlos Romero-Nieto,

    1. Department of Chemistry and Pharmacy and Interdisciplinary Center of Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany)
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  • Prof. Dirk M. Guldi,

    1. Department of Chemistry and Pharmacy and Interdisciplinary Center of Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany)
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  • Dr. Benoit Heinrich,

    1. IPCMS - UMR 7504 (CNRS/Université de Strasbourg), 23, rue du Loess, BP 43, 67034 Strasbourg CEDEX 2 (France)
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  • Dr. Bertrand Donnio,

    1. IPCMS - UMR 7504 (CNRS/Université de Strasbourg), 23, rue du Loess, BP 43, 67034 Strasbourg CEDEX 2 (France)
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  • Dr. Stéphane Campidelli

    Corresponding author
    1. IRAMIS, Laboratoire d'Electronique Moléculaire, SPEC (URA 2464), CEA-Saclay, 91191 Gif-sur-Yvette (France), Fax: (+33) 1-69-08-66-40
    • IRAMIS, Laboratoire d'Electronique Moléculaire, SPEC (URA 2464), CEA-Saclay, 91191 Gif-sur-Yvette (France), Fax: (+33) 1-69-08-66-40

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Abstract

Herein the synthesis, characterization, and organization of a first-generation dendritic fulleropyrrolidine bearing two pending porphyrins are reported. Both the dendron and the fullerene derivatives were synthesized by CuI-catalyzed alkyne–azide cycloaddition (CuAAC). The electron-donor–acceptor conjugate possesses a shape that allows the formation of supramolecular complexes by encapsulation of C60 within the jaws of the two porphyrins of another molecule. The interactions between the two photoactive units (i.e., C60 and Zn–porphyrin) were confirmed by cyclic voltammetry as well as by steady-state and time-resolved spectroscopy. For example, a shift of about 85 mV was found for the first reduction of C60 in the electron-donor–acceptor conjugate compared with the parent molecules, which indicates that C60 is included in the jaws of the porphyrin. The fulleropyrrolidine compound exhibits a rich polymorphism, which was corroborated by AFM and SEM. In particular, it was found to form supramolecular fibrils when deposited on substrates. The morphology of the fibrils suggests that they are formed by several rows of fullerene–porphyrin complexes.

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