Abstract
Retinal is the molecule found in photoreceptor cells that undergoes a change in shape when it absorbs light. Specifically, the cis/trans isomerization of a carbon–carbon double bond in this chromophore sets in motion the chain of biochemical processes responsible for vision1,2,3. Here, we obtain atomically resolved images of individual structural isomers of the retinal chromophore attached to C60 molecules and study their dynamic behaviour inside a confined space—that is, inside single-walled carbon nanotubes—using high-resolution transmission electron microscopy (HR-TEM). Sequential HR-TEM images with sub-second time resolution directly reveal the isomerization between the cis and all-trans forms of retinal, as well as conformational changes and volume-conserving effects. This work opens up the possibility of investigating in vitro the biological activities of these photoresponsive molecules on an individual basis, and the molecular imaging technique described here is a general one that can be applied to a wide range of systems.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Rent or buy this article
Prices vary by article type
from$1.95
to$39.95
Prices may be subject to local taxes which are calculated during checkout




Similar content being viewed by others
References
Zechmeister, L. in Cis–trans Isomeric Carotenoids, Vitamin A, and Aryl Polyenes (Academic Press, New York, 1962).
Spudich, J. L., Yang, C., Jung, K. & Spudich, E.N. Retinylidene proteins: Structures and functions from archaea to humans. Annu. Rev. Cell Dev. Biol. 16, 365–392 (2000).
Pebay-Peyroula, E., Rummel, G., Rosenbusch, J. & Landau, E. M. X-ray structure of bacteriodhodopsin at 2.5 angstroms from microscrystals grown in lipid cubic phases. Science 277, 1676–1681 (1997).
Liu, Z. et al. Transmission electron microscopy imaging of individual functional groups of fullerene derivatives. Phys. Rev. Lett. 96, 088304 (2006).
Koshino, M. et al. Imaging of single organic molecules in motion. Science 316, 853 (2007).
Suenaga, K. et al. Element selective single atom imaging. Science 290, 2280–2282 (2000).
Hirahara, K. et al. Electron diffraction study of one-dimensional crystals of fullerenes. Phys. Rev. B 64, 115420 (2001).
Liu, R. S. H. Photoisomerization by Hula-twist. Photoactive biopigments. Pure Appl. Chem. 74, 1391–1396 (2002).
Reimer, L. in Physical Aspects of Electron Microscopy and Microbeam Analysis (ed. Siegel, B. M. & Beaman, D. R.) 231–245 (Wiley, New York, 1975).
Egerton, R., Li, P. & Malac, M. Radiation damage in the TEM and SEM. Micron 35, 399–409 (2004).
Kobayashi, T., Saito, T. & Ohtani, H. Real-time spectroscopy of transition states in bacteriorhodopsin during retinal isomerization. Nature 414, 531–534 (2001).
Yamazaki, M., Araki, Y., Fujitsuka, M. & Ito, O. Photoinduced microsecond-charge-separation in retinyl-C60 dyad. J. Phys. Chem. A 105, 8615–8622 (2001).
Kataura, H. et al. High-yield fullerene encapsulation in single-wall carbon nanotubes. Synth. Met. 121, 1195–1196 (2001).
Kirkland, E. J. in Advanced Computing in Electron Microscopy, 106–117 (Plenum Press, New York, 1998).
Acknowledgements
Work on electron microscopy was supported by CREST. K.Y. thanks M. Funabashi for his help in a mass spectroscopy experiment. The partial support of a Grant-in-Aid for Scientific Research from MEXT is also acknowledged by K.Y. and H.K.
Author information
Authors and Affiliations
Contributions
K.Y. and H.K. designed the molecules and contributed the materials. Z.L. performed the experiments. Z.L. and K.S. analysed the data. K.S. and S.I. designed and conceived the experiments. Z.L., K.Y. and K.S co-wrote the paper. All authors discussed the results and commented the manuscript.
Corresponding author
Ethics declarations
Competing interests
The authors declare no competing financial interests.
Supplementary information
Supplementary Information
Supplementary figures S1 and S2, and captions to supplementary movies (PDF 395 kb)
Supplementary Information
Supplementary movie 1a (MOV 109 kb)
Supplementary Information
Supplementary movie 1b (MOV 188 kb)
Supplementary Information
Supplementary movie 1c (MOV 51 kb)
Supplementary Information
Supplementary movie 1d (MOV 85 kb)
Supplementary Information
Supplementary movie 1e (MOV 122 kb)
Supplementary Information
Supplementary movie 2a (MOV 13 kb)
Supplementary Information
Supplementary movie 2b (MOV 13 kb)
Supplementary Information
Supplementary movie 2c (MOV 17 kb)
Supplementary Information
Supplementary movie 2d (MOV 41 kb)
Supplementary Information
Supplementary movie 2e (MOV 13 kb)
Rights and permissions
About this article
Cite this article
Liu, Z., Yanagi, K., Suenaga, K. et al. Imaging the dynamic behaviour of individual retinal chromophores confined inside carbon nanotubes. Nature Nanotech 2, 422–425 (2007). https://doi.org/10.1038/nnano.2007.187
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1038/nnano.2007.187
This article is cited by
-
Atomic imaging of zeolite-confined single molecules by electron microscopy
Nature (2022)
-
CVD growth of 1D and 2D sp2 carbon nanomaterials
Journal of Materials Science (2016)
-
Nano-confinement of biomolecules: Hydrophilic confinement promotes structural order and enhances mobility of water molecules
Nano Research (2016)
-
Encapsulation of sodium radio-iodide in fullerene C60
Journal of Molecular Modeling (2014)
-
Direct imaging of hydrogen-atom columns in a crystal by annular bright-field electron microscopy
Nature Materials (2011)