The self-assembly of organic molecules into supramolecular materials with structural ordering beyond the nanometre scale is challenging. Here, we report the spontaneous self-assembly of a chiral discotic triphenylene derivative into millimetre-sized droplets. The structure of the droplets is characterized by high positional and orientational ordering and a three-dimensional integrity similar to that of single crystals. Notwithstanding, these assemblies slide when placed on a vertical substrate demonstrating their fluid nature. X-ray imaging shows that during the sliding process the internal crystal-like structure is maintained and that the droplets undergo clockwise or counterclockwise unidirectional rotation, depending on the chirality of their molecular components. Rheological measurements suggest that this rotational behaviour might result from the distinct yield stress between the (R)- and (S)-enantiomers. Overall, our findings demonstrate that molecular chirality can determine the movement direction of a supramolecular structure, thus expanding the fundamental understanding of the structure and dynamics of soft materials.

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Crystal data of (R)-2 is available from the Cambridge Crystallographic Data Centre (CCDC) under reference number 1824673. Any other data supporting the findings of this study are available within the article and its supplementary files and available from the authors upon reasonable request.

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  1. 1.

    Hahn, T. International Tables for Crystallography, Volume A: Space-Group Symmetry 5th edn (Kluwer Academic, Dordrecht, 2002).

  2. 2.

    Stewart, I. W. in Handbook of Liquid Crystals Vol. 1, 2nd edn (eds Goodby, J. W. et al.) Ch. 4 (Wiley, Weinheim, 2014).

  3. 3.

    Gavezzotti, A. & Simonetta, M. Crystal chemistry in organic solids. Chem. Rev. 82, 1–13 (1982).

  4. 4.

    Osawa, T. et al. Wide-range 2D lattice correlation unveiled for columnarly assembled triphenylene hexacarboxylic esters. Angew. Chem. Int. Ed. 51, 7990–7993 (2012).

  5. 5.

    Wöhrle, T. Discotic liquid crystals. Chem. Rev. 116, 1139–1241 (2016).

  6. 6.

    Zhang, S. et al. Synthesis and mesophase of a chiral triphenylene-based discotic liquid crystal. Appl. Mech. Mater. 748, 107–110 (2015).

  7. 7.

    Takezoe, H. Historical overview of polar liquid crystals. Ferroelectrics 468, 1–17 (2014).

  8. 8.

    Bushby, R. J. & Lozman, O. R. Discotic liquid crystals 25 years on. Curr. Opin. Colloid Interface Sci. 7, 343–354 (2002).

  9. 9.

    Nuckolls, C. & Katz, T. J. Synthesis, structure, and properties of a helical columnar liquid crystal. J. Am. Chem. Soc. 120, 9541–9544 (1998).

  10. 10.

    Scherowsky, G. & Chen, X. H. Structural studies of columnar phases of some chiral disc-like molecules. Liq. Cryst. 24, 157–162 (1998).

  11. 11.

    Green, M. M., Ringsdorf, H., Wagner, J. & Wiistefeld, R. Induction and variation of chirality in discotic liquid crystalline polymers. Angew. Chem. Int. Ed. Engl. 29, 1478–1481 (1990).

  12. 12.

    Dierking, I. Textures of Liquid Crystals (Wiley, Weinheim, 2003).

  13. 13.

    Agra-Kooijman, D. M. & Kumar, S. in Handbook of Liquid Crystals Vol. 1, 2nd edn (eds Goodby, J. W. et al.) Ch. 10 (Wiley, Weinheim, 2014).

  14. 14.

    Goodby, J. W. in Handbook of Liquid Crystals 2nd edn (eds. Goodby, J. W. et al.) Vol. 4, Ch. 2 (Wiley-VCH, Weinheim 2014).

  15. 15.

    Getmanenko, Y. A. et al. Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors. J. Mater. Chem. C 2, 2600–2611 (2014).

  16. 16.

    Gane, P. A. C., Leadbetter, A. J. & Wrighton, P. G. Structure and correlations in smectic B, F and I phases. Mol. Cryst. Liq. Cryst. 66, 247–266 (1981).

  17. 17.

    Leadbetter, A. J., Frost, J. C., Gaughan, J. P. & Mazid, M. A. The structure of the crystal, smectic E and smectic B forms of IBPBAC. J. Physique Colloques 40, C3-185–C3-192 (1979).

  18. 18.

    Davis, E. J. & Goodby, J. W. in Handbook of Liquid Crystals Vol. 1, 2nd edn (eds Goodby, J. W. et al.) Ch. 7 (Wiley, Weinheim, 2014).

  19. 19.

    Pasechnik, S. V., Chigrinov, V. G. & Shmeliova, D. V. in Liquid Crystals: Viscous and Elastic Properties Ch. 3 (Wiley, Weinheim, 2009).

  20. 20.

    Malkin, A. Y. Non-Newtonian viscosity in steady-state shear flows. J. Nonnewton. Fluid Mech. 192, 48–65 (2013).

  21. 21.

    Fujii, S., Komura, S., Ishii, Y. & Lu, C.-Y. D. Elasticity of smectic liquid crystals with focal conic domains. J. Phys. Condens. Matter 23, 235105 (2011).

  22. 22.

    Pasechnik, S. V., Chigrinov, V. G. & Shmeliova, D. V. in Liquid Crystals: Viscous and Elastic Properties Ch. 2 (Wiley, Weinheim, 2009).

  23. 23.

    Mezzenga, R. et al. Shear rheology of lyotropic liquid crystals: a case study. Langmuir 21, 3322–3333 (2005).

  24. 24.

    Hamley, I. W. in Introduction to Soft Matter–Revised Edition: Synthetic and Biological Self-Assembling Materials Ch. 1 (Wiley, Chichester, 2007).

  25. 25.

    Münstedt, H. & Schwarzl, F. R. Deformation and Flow of Polymeric Materials (Springer, Heidelberg, 2014).

  26. 26.

    Mori, T. & Matsumoto, T. Viscoelastic properties of fatty acid soap/water colloidal systems. J. Soc. Rheol. Jpn 27, 183–187 (1999).

  27. 27.

    Seiki, N. et al. Rational synthesis of organic thin films with exceptional long-range structural integrity. Science 348, 1122–1126 (2015).

  28. 28.

    Yokota, T. et al. A few-layer molecular film on polymer substrates to enhance the performance of organic devices. Nat. Nanotech. 13, 139–144 (2018).

  29. 29.

    Otera, J., Danoh, N. & Nozaki, H. Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification. J. Org. Chem. 56, 5307–5311 (1991).

  30. 30.

    Hammersley, A. FIT2D v.17.006 (European Synchrotron Radiation Facility, 2015); http://www.esrf.eu/computing/scientific/FIT2D/

  31. 31.

    Miura, H. CellCalc: a unit cell parameter refinement program on Windows computer. J. Crystallogr. Soc. Jpn 45, 145–147 (2003).

  32. 32.

    SAINT version V7.60A (Bruker AXS Inc., Madison, 2009).

  33. 33.

    Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination. J. Appl. Crystallogr. 48, 3–10 (2015).

  34. 34.

    Altomare, A. M. et al. SIR97: a new tool for crystal structure determination and refinement. J. Appl. Cryst. 32, 115–119 (1999).

  35. 35.

    Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. Sect. A 64, 112–122 (2008).

  36. 36.

    Torchia, D. A. The measurement of proton-enhanced carbon-13 T 1 values by a method which suppresses artifacts. J. Magn. Reson. 30, 613–616 (1978).

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This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “π-Figuration” (26102008) from The Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, and KAKENHI (17H01034) from the Japan Society for the Promotion of Science (JSPS). This work was also supported in part by “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” from MEXT, Japan. The synchrotron XRD experiments were performed at the BL45XU beamline in the SPring-8 with the approval of the RIKEN SPring-8 Center (proposal numbers 20140056, 20150068, 20160027 and 20170055). We thank Y. Shinozaki (Anton Paar Japan) for his assistance with the dynamic viscoelasticity measurements of (R)-2. We are grateful to S.-i. Adachi and R. Kumai (High Energy Accelerator Research Organization) and G. Ungar and X. Zeng (The University of Sheffield) for very valuable discussions about structural characterization. The authors would also like to thank Suzukakedai Materials Analysis Division, Technical Department, Tokyo Institute of Technology, for their support with the NMR measurements.

Author information


  1. Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Yokohama, Japan

    • Takashi Kajitani
    • , Kyuri Motokawa
    • , Atsuko Kosaka
    • , Yoshiaki Shoji
    •  & Takanori Fukushima
  2. RIKEN SPring-8 Center, Sayo, Hyogo, Japan

    • Takashi Kajitani
    • , Takaaki Hikima
    •  & Masaki Takata
  3. Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization, Tsukuba, Japan

    • Rie Haruki
  4. RIKEN Center for Emergent Matter Science (CEMS), Wako, Saitama, Japan

    • Daisuke Hashizume
  5. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Aoba-ku, Sendai, Japan

    • Masaki Takata
  6. JEOL Resonance Inc., Akishima, Tokyo, Japan

    • Koji Yazawa
  7. Institute for Protein Research, Osaka University, Suita, Osaka, Japan

    • Koji Yazawa
  8. Institute for Solid State Physics, The University of Tokyo, Kashiwa, Chiba, Japan

    • Ken Morishima
    •  & Mitsuhiro Shibayama


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T.K. and T.F. designed the project. K.Motokawa, A.K. and T.K. carried out the synthesis and characterization of the materials. T.K., D.H., R.H., T.H. and M.T. performed the X-ray diffraction analysis. Y.S. performed the single-crystal X-ray analysis. K.Y. performed the solid-state 1H and 13C NMR measurements and analysis. T.K., K. Morishima and M.S. performed the rheological measurements and analysed the data. T.K., K. Morishima, M.S. and T.F. co-wrote the manuscript.

Competing interests

The authors declare no competing interests.

Corresponding author

Correspondence to Takanori Fukushima.

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