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Imaging the passage of a single hydrocarbon chain through a nanopore

Nature Nanotechnology volume 3, pages 595–597 (2008)Cite this article

Abstract

Molecular transport through nanoscale pores in films, membranes and wall structures is of fundamental importance in a number of physical, chemical and biological processes1,2,3,4,5,6. However, there is a lack of experimental methods that can obtain information on the structure and orientation of the molecules as they pass through the pore, and their interactions with the pore during passage. Imaging with a transmission electron microscope is a powerful method for studying structural changes in single molecules as they move7,8 and for imaging molecules confined inside carbon nanotubes9. Here, we report that such imaging can be used to observe the structure and orientation of a hydrocarbon chain as it passes through nanoscale defects in the walls of a single-walled carbon nanotube to the vacuum outside, and also to study the interactions between the chain and the nanopore. Based on experiments at 293 K and 4 K we conclude that the major energy source for the molecular motions observed at 4 K is the electron beam used for the imaging.

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Figure 1: The sample molecules.
Figure 2: Alkenyl fullerene in a carbon nanotube.
Figure 3: Alkenyl fullerene and alkyl fullerene in a carbon nanotube.

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References

  1. Mulder, M. Basic Principles of Membrane Technology 1st edn (Kluwer, Dordrecht, 1991).

    Book  Google Scholar 

  2. Rao, M. B. & Sircar, S. Nanoporous carbon membranes for separation of gas mixtures by selective surface flow. J. Membrane Sci. 85, 253–264 (1993).

    Article  CAS  Google Scholar 

  3. Holt, J. K. et al. Fast mass transport through sub-2-nanometre carbon nanotubes. Science 312, 1034–1037 (2006).

    Article  CAS  Google Scholar 

  4. Borgnia, M., Nielsen, S., Engel, A. & Agre, P. Cellular and molecular biology of the aquaporin water channels. Annu. Rev. Biochem. 68, 425–458 (1999).

    Article  CAS  Google Scholar 

  5. Isobe, H., Homma, T. & Nakamura, E. Energetics of water permeation through fullerene membrane. Proc. Natl Acad. Sci.USA 104, 14895–14898 (2007).

    Article  CAS  Google Scholar 

  6. Kasianowicz, J. J. et al. Characterization of individual polynucleotide molecules using a membrane channel. Proc. Natl Acad. Sci.USA 93, 13770–13773 (1996).

    Article  CAS  Google Scholar 

  7. Koshino, M. et al. Imaging of single organic molecules in motion. Science 316, 853 (2007).

    Article  CAS  Google Scholar 

  8. Solin, N. et al. Imaging of aromatic amide molecules in motion. Chem. Lett. 36, 1208–1209 (2007).

    Article  CAS  Google Scholar 

  9. Liu, Z. et al. Imaging the dynamic behaviour of individual retinal chromophores confined inside carbon nanotubes. Nature Nanotech. 2, 422–425 (2007).

    Article  CAS  Google Scholar 

  10. Hirsch, A., Soi, H. & Karfunkel, R. Titration of C60: A method for the synthesis of organofullerenes. Angew. Chem. Int. Ed. Engl. 31, 766–768 (1992).

    Article  Google Scholar 

  11. Hashimoto, A. et al. Selective deposition of a one-atom to a multi-atom gadolinium(iii) cluster in a hole opening of single-wall carbon nanohorn. Proc. Natl Acad. Sci. USA 101, 8527–8530 (2004).

    Article  CAS  Google Scholar 

  12. Suenaga, K. et al. Imaging active topological detects in carbon nanotubes. Nature Nanotech. 2, 358–360 (2007).

    Article  CAS  Google Scholar 

  13. Meyer, J. C. et al. Direct imaging of lattice atoms and topological defects in graphene membranes. Nano Lett. (2008) DOI: 10.1021/nl801386 m.

  14. Nishio, M., Umezawa, Y., Hirota, M. & Takeuchi, Y. The CH/π interaction: Significance in molecular recognition. Tetrahedron 51, 8665–8701 (1995).

    Article  CAS  Google Scholar 

  15. Liu, Z., Suenaga, K. & Iijima, S. Imaging the structure of an individual C60 fullerene molecule and its deformation process using HRTEM with atomic sensitivity. J. Am. Chem. Soc. 129, 6666–6667 (2007).

    Article  CAS  Google Scholar 

  16. Nakamura, E. et al. Imaging of conformational change of biotinylated triamide molecules covalently bonded to carbon nanotube surface. J. Am. Chem. Soc. 130, 7808–7809 (2008).

    Article  CAS  Google Scholar 

  17. Cosslett, V. E. Radiation damage in the high resolution electron microscopy of biological materials: A review. J. Microsc. 113, 113–129 (1978).

    Article  CAS  Google Scholar 

  18. Bandosz, T. J. et al. Chemistry and Physics of Carbon, Vol. 28, 41–228 (Marcel Dekker, New York, 2003).

    Google Scholar 

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Acknowledgements

Electron microscopy experiments were performed in collaboration with the Nanotube Research Centre, the National Institute of Advanced Industrial Science and Technology (AIST). We thank K. Yamanouchi for helpful discussions. This study was partly supported by MEXT (KAKENHI no. 18655012 to E.N.) and the Sumitomo Foundation (to H.I.). N.S. wishes to thank the Knut och Alice Wallenbergs stiftelse (Stockholm, Sweden) for a postdoctoral fellowship and T.T. thanks the Japan Society for Promotion of Science for a predoctoral fellowship.

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  1. Niclas Solin & Hiroyuki Isobe

    Present address: Present address: Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, 10691 Stockholm, Sweden (N.S.); Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan (H.I.),

Authors and Affiliations

  1. Exploratory Research for Advanced Technology (ERATO), Nakamura Functional Carbon Cluster Project, Japan Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan

    Masanori Koshino & Eiichi Nakamura

  2. Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan

    Niclas Solin, Takatsugu Tanaka, Hiroyuki Isobe & Eiichi Nakamura

Authors
  1. Masanori Koshino
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  2. Niclas Solin
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  3. Takatsugu Tanaka
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  4. Hiroyuki Isobe
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  5. Eiichi Nakamura
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Contributions

M.K., H.I. and E.N. conceived and designed the experiments. N.S. contributed materials/analysis tools. M.K., H.I. and E.N. co-wrote the paper. All authors discussed the results and commented on the manuscript. N.S., T.T., H.I. and E.N. were responsible for synthesis of organic molecules and their analysis. M.K. was responsible for peapod sample preparations, TEM measurements and their analysis.

Corresponding authors

Correspondence to Hiroyuki Isobe or Eiichi Nakamura.

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Koshino, M., Solin, N., Tanaka, T. et al. Imaging the passage of a single hydrocarbon chain through a nanopore. Nature Nanotech 3, 595–597 (2008). https://doi.org/10.1038/nnano.2008.263

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