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A Bis(C60)–Bis(phthalocyanine) Nanoconjugate: Synthesis and Photoinduced Charge Transfer

Authors

  • Axel Kahnt,

    1. Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany, Fax: (+49) 9131-8528307
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  • Maurizio Quintiliani Dr.,

    1. Departamento de Química Orgánica (C-I), Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-4973966
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  • Purificación Vázquez Prof.,

    1. Departamento de Química Orgánica (C-I), Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-4973966
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  • Dirk M. Guldi Prof.,

    1. Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany, Fax: (+49) 9131-8528307
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  • Tomás Torres Prof.

    1. Departamento de Química Orgánica (C-I), Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-4973966
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Abstract

A novel dimeric phthalocyanine–C60 nanoconjugate, consisting of a bisphthalocyanine core to which two fullerenes are attached, has been prepared. The synthetic strategy implemented the preparation of a diformyl butadiynyl-bridged bisphthalocynaninatozinc(II) complex by means of palladium-catalyzed cross-coupling reactions and subsequent dipolar cycloaddition reactions. Photophysical experiments confirm that an intramolecular electron transfer, namely, from the photoexcited ZnPc moiety to the electron-accepting C60 unit, governs the overall photoreactivity of the nanoconjugate. Through-space charge-transfer interactions facilitated by the close proximity of the ZnPc and the C60 moieties play a decisive role in determining the lifetimes of the charge-separated state which range from 10−10to 10−9seconds.

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