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Manipulating single-wall carbon nanotubes by chemical doping and charge transfer with perylene dyes

Nature Chemistry volume 1, pages 243–249 (2009)Cite this article

Abstract

Single-wall carbon nanotubes (SWNTs) are emerging as materials with much potential in several disciplines, in particular in electronics and photovoltaics. The combination of SWNTs with electron donors or acceptors generates active materials, which can produce electrical energy when irradiated. However, SWNTs are very elusive species when characterization of their metastable states is required. This problem mainly arises because of the polydispersive nature of SWNT samples and the inevitable presence of SWNTs in bundles of different sizes. Here, we report the complete and thorough characterization of an SWNT radical ion-pair state induced by complexation with a perylene dye, which combines excellent electron-accepting and -conducting features with a five-fused ring π-system. At the same time, the perylene dye enables the dispersion of SWNTs by means of π–π interactions, which gives individual SWNTs in solution. This work clears a path towards electronic and optoelectronic devices in which regulated electrical transport properties are important.

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Figure 1: Spectroelectrochemistry of SWNT–SDBS.
Figure 2: Spectroscopic and microscopic characterization of SWNT–1.
Figure 3: Raman characterization of SWNT–SDBS and SWNT–1.
Figure 4: Visible and near-infrared fluorescence of 1, SWNT–SDBS and SWNT–1.
Figure 5: Photophysics of SWNT–1.
Figure 6: Spectroelectrochemistry of SWNT–1.

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Acknowledgements

This work was carried out with financial support from the Deutsche Forschungsgemeinschaft, Cluster of Excellence ‘Engineering of Advanced Materials’, Fonds der Chemischen Industrie, the Office of Basic Energy Sciences of the US, University of Trieste, Giovani Ricercatori Program, Consorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali, Ministero dell'Istruzione, dell'Università e della Ricerca, and Freiburg Institute for Advanced Studies (Junior Research Fellowship). We thank C. Gamboz and J. Röhrl for their assistance with TEM imaging and Raman microscopy, respectively.

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Authors and Affiliations

  1. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, Erlangen, 91058, Germany

    Christian Ehli, Christian Oelsner & Dirk M. Guldi

  2. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Trieste, Piazzale Europa 1, Trieste, 34127, Italy

    Aurelio Mateo-Alonso & Maurizio Prato

  3. Albert-Ludwigs-Universität Freiburg, Freiburg Institute for Advanced Studies, Institut für Organische Chemie und Biochemie, Albertstrasse 21, Freiburg im Breisgau, D-79104, Germany

    Aurelio Mateo-Alonso

  4. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, Erlangen, 91054, Germany

    Cordula Schmidt, Claudia Backes, Frank Hauke & Andreas Hirsch

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  1. Christian Ehli
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Contributions

C.E. performed and interpreted all steady-state and time-resolved absorption and emission measurements and the electrochemical experiments. D.M.G. interpreted the data, supervised the research and wrote the manuscript. C.O. performed and interpreted the Raman microscope and in situ Raman measurements. A.M.A. performed and interpreted AFM and TEM data. M.P. helped to analyse the data and write the manuscript. C.S. synthesized the detergents. C.B. provided expertise on the dispersion of SWNTs. F.H. supervised the chemistry and SWNT dispersion. A.H. supervised the synthesis of the detergents.

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Correspondence to Dirk M. Guldi.

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Ehli, C., Oelsner, C., Guldi, D. et al. Manipulating single-wall carbon nanotubes by chemical doping and charge transfer with perylene dyes. Nature Chem 1, 243–249 (2009). https://doi.org/10.1038/nchem.214

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