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Issue 5, 2011
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Photoinduced electron transfer in a clicked fullerene–porphyrin conjugate

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Abstract

A stable C60 derivative bearing an azide functional group has been prepared and used as a building block for the preparation of a fullereneporphyrin conjugate (F–P–F) by reaction with a Zn(II)porphyrin bearing two terminal alkyne groups under the copper mediated Huisgen 1,3-dipolar cycloaddition conditions. The electrochemical and photophysical properties of the resulting multicomponent system have been investigated in detail. In benzonitrile, F–P–F undergoes photoinduced electron transfer and the resulting charge separated state is relatively long lived (τ = 0.48 µs). In contrast, intramolecular energy transfer has been evidenced in toluene, with the generation of the fullerene triplet level upon selective excitation of the porphyrin moiety. In this solvent, a CT emission band is observed in the near-infrared region (λmax = 940 nm) as a consequence of a conformational equilibrium causing, to a minor extent, the formation of intramolecular porphyrinfullerene tight pairs. This finding is supported by measurements of singlet oxygen sensitization and quenching of the long-lived fullerene centered triplet state in the oxygen free solution.

Graphical abstract: Photoinduced electron transfer in a clicked fullerene–porphyrin conjugate

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Article information


Submitted
16 Jul 2010
Accepted
08 Oct 2010
First published
09 Nov 2010

J. Mater. Chem., 2011,21, 1562-1573
Article type
Paper

Photoinduced electron transfer in a clicked fullereneporphyrin conjugate

J. Iehl, M. Vartanian, M. Holler, J. Nierengarten, B. Delavaux-Nicot, J. Strub, A. Van Dorsselaer, Y. Wu, J. Mohanraj, K. Yoosaf and N. Armaroli, J. Mater. Chem., 2011, 21, 1562
DOI: 10.1039/C0JM02310H

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