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

Nature Chemistry volume 1, pages 243249 (2009) | Download Citation



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 ππ 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.

  • Compound C56H60N4O18


  • Compound C21H20BrNO

    Trimethyl-(2-oxo-2-pyren-1-yl-ethyl)-ammonium bromide

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  1. 1.

    & Nanoelectronics from the bottom up. Nature Mater. 6, 841–850 (2007).

  2. 2.

    & Electronically monitoring biological interactions with carbon nanotube field-effect transistors. Chem. Soc. Rev. 37, 1197–1206 (2008).

  3. 3.

    , & Functionalized carbon nanotubes in drug design and discovery. Acc. Chem. Res. 41, 60–68 (2008).

  4. 4.

    , , , , & Optimized carbon nanotube fiber microelectrodes as potential analytical tools. Anal. Bioanal. Chem. 389, 499–505 (2007).

  5. 5.

    , & Separation of metallic and semiconducting single-walled carbon nanotubes via covalent functionalization, Small 3, 1672–1676 (2007).

  6. 6.

    et al. Nanotube molecular wires as chemical sensors. Science 287, 622–625 (2000).

  7. 7.

    , , & Extreme oxygen sensitivity of electronic properties of carbon nanotubes. Science 287, 1801–1804 (2000).

  8. 8.

    , , , & Gas sensor array on metal-decorated carbon nanotubes. J. Phys. Chem. B 110, 21014–21020 (2006).

  9. 9.

    , & Amphoteric doping of single-wall carbon-nanotube thin films as probed by optical absorption spectroscopy. Phys. Rev. B 60, 13339–13342 (1999).

  10. 10.

    et al. Effects of nanodomain formation on the electronic structure of doped carbon nanotubes. Phys. Rev. Lett. 81, 2332–2335 (1998).

  11. 11.

    , , & A tunable photosensor. J. Am. Chem. Soc. 130, 16996–17003 (2008).

  12. 12.

    , , & Multifunctional molecular carbon materials – from fullerenes to carbon nanotubes. Chem. Soc. Rev. 35, 471–487 (2006).

  13. 13.

    , , & Chemistry of carbon nanotubes. Chem. Rev. 106, 1105–1136 (2006).

  14. 14.

    et al. Singling out the electrochemistry of individual single-walled carbon nanotubes in solution. J. Am. Chem. Soc. 130, 7393–7399 (2008).

  15. 15.

    et al. Spectroscopic characterization of photolytically generated radical ion pairs in single-wall carbon nanotubes bearing surface-immobilized tetrathiafulvalenes. J. Am. Chem. Soc. 130, 66–73 (2008).

  16. 16.

    , & Synthesis and aggregation properties of water-soluble Newkome-dendronized perylenetetracarboxdiimides. Eur. J. Org. Chem. 5497–5505 (2007).

  17. 17.

    et al. Structure-assigned optical spectra of single-walled carbon nanotubes. Science 298, 2361–2366 (2002).

  18. 18.

    , & Solubilization of single-walled carbon nanotubes by using polycyclic aromatic ammonium amphiphiles in water—strategy for the design of high-performance solubilizers. Chem. Eur. J. 12, 4027–4034 (2006).

  19. 19.

    et al. Photophysics of a water-soluble rylene dye: comparison with other fluorescent molecules for biological applications. J. Phys. Chem. B 108, 12242–12251 (2004).

  20. 20.

    , & Ultrafast photoswitched charge transmission through the bridge molecule in a donor–bridge–acceptor system. J. Am. Chem. Soc. 122, 5563–5567 (2000).

  21. 21.

    et al. Photoinduced electron and energy transfer processes in a bichromophoric pyrene–perylene bisimide system. J. Phys. Chem. A 108, 1900–1909 (2004).

  22. 22.

    , & Radiolytic reduction of a water-soluble fullerene cluster. J. Phys. Chem. A 101, 1783–1786 (1997).

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

    • Christian Ehli
    • , Christian Oelsner
    •  & Dirk M. Guldi
  2. Università degli Studi di Trieste, Dipartimento di Scienze Farmaceutiche, Piazzale Europa 1, 34127 Trieste, Italy

    • Aurelio Mateo-Alonso
    •  & Maurizio Prato
  3. Albert-Ludwigs-Universität Freiburg, Freiburg Institute for Advanced Studies, Institut für Organische Chemie und Biochemie, Albertstrasse 21, D-79104 Freiburg im Breisgau, Germany

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

    • Cordula Schmidt
    • , Claudia Backes
    • , Frank Hauke
    •  & Andreas Hirsch


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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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