Download PDF
Synthesis 2011(23): 3801-3806  
DOI: 10.1055/s-0031-1289573
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Click Chemistry Applied in the Synthesis of Symmetrical Triphenylene-Based Discotic Liquid-Crystalline Dimers

Damien Thevenet, Reinhard Neier*
Department of Chemistry, University of Neuchâtel, Avenue de Bellevaux 51, 2000 Neuchâtel, Switzerland
Fax: +41(32)7182511; e-Mail: reinhard.neier@unine.ch;
Further Information

Publication History

Received 25 July 2011
Publication Date:
21 October 2011 (online)

   Permissions and Reprints All articles of this category

Abstract

Symmetrical triphenylene dimers connected by a bis-triazole moiety have been synthesized and characterized. The bis-triazole part is formed as final step utilizing a straightforward double click reaction (CuAAC) allowing further structural variations of the linker. The 1,3-bis(triazol-1-yl)propyltriphenylene-based dimer display columnar mesophase over a wide range of temperatures starting at ambient temperature.

Key words

discotic - columnar mesophase - liquid-crystal dimer - triphenylene - click chemistry - azide-alkyne cycloaddition

    References

  • 1a Bushby RJ. Lozman OR. Curr. Opin. Colloid Interface Sci.  2002,  7:  343 
    Search in Google Scholar
  • 1b Kumar S. Chem. Soc. Rev.  2006,  35:  83 
    Search in Google Scholar
  • 1c Sergeyev S. Pisula W. Geerts YH. Chem. Soc. Rev.  2007,  36:  1902 
    Search in Google Scholar
  • 1d Laschat S. Baro A. Steincke N. Giesselmann F. Hagele C. Scalia G. Judele R. Kapatsina E. Sauer S. Schreivogel A. Tosoni M. Angew. Chem. Int. Ed.  2007,  46:  4832 
    Search in Google Scholar
  • 1e Wu JS. Pisula W. Müllen K. Chem. Rev.  2007,  107:  718 
    Search in Google Scholar
  • 2a Adam D. Haarer D. Clos F. Frey T. Funhoff D. Siemensmeyer K. Schumacher P. Ringsdorf H. Ber. Bunsen-Ges. Phys. Chem.  1993,  97:  1366 
    Search in Google Scholar
  • 2b Adam D. Schumacher P. Simmerer J. Haussling L. Siemensmeyer K. Etzbach KH. Ringsdorf H. Haarer D. Nature  1994,  371:  141 
    Search in Google Scholar
  • 2c Schmidt-Mende L. Fechtenkoetter A. Müllen K. Moons E. Friend RH. MacKenzie JD. Science  2001,  293:  1119 
    Search in Google Scholar
  • 2d Warman JM. Van De Craats AM. Mol. Cryst. Liq. Cryst.  2003,  396:  41 
    Search in Google Scholar
  • 2e Duzhko V. Semyonov A. Twieg RJ. Singer KD. Phys. Rev. B.  2006,  73:  064201 
    Search in Google Scholar
  • 3 Feng X. Marcon V. Pisula W. Hansen M. Kirkpatrick J. Grozema F. Andrienko D. Kremer K. Müllen K. Nat. Mater.  2009,  8:  421 
    Search in Google Scholar
  • 4a Demus D. Goodby J. Gray GW. Spiess H.-W. Vill V. In Handbook of Liquid Crystals   Wiley-VCH; Weinheim: 1998. 
  • 4b Lehn J.-M. In Supramolecular Chemistry   VCH; Weinheim: 1995. 
  • 5a Billard J. Dubois JC. Nguyen HT. Zann A. Nouv. J. Chim.  1978,  2:  535 
    Search in Google Scholar
  • 5b Levelut AM. J. Phys. Lett.  1979,  40:  L81 
    Search in Google Scholar
  • 5c Cammidge AN. Bushby RJ. Handbook of Liquid Crystals   Vol. 2B:  Demus D. Goodby J. Gray GW. Spiess H.-W. Vill V. Wiley-VCH; Weinheim: 1998.  Chap. VII.
    Search in Google Scholar
  • 5d Kumar S. Liq. Cryst.  2004,  31:  1037 
    Search in Google Scholar
  • 5e Kumar S. Chem. Soc. Rev.  2006,  35:  83 
    Search in Google Scholar
  • 6 Kumar S. Liq. Cryst.  2005,  32:  1089 
    Search in Google Scholar
  • 7a Imrie CT. Henderson PA. Curr. Opin. Colloid Interface Sci.  2002,  7:  298 
    Search in Google Scholar
  • 7b Imrie CT. Henderson PA. Chem. Soc. Rev.  2007,  36:  2093 
    Search in Google Scholar
  • 8a Kreuder W. Ringsdorf H. Makromol. Chem., Rapid Commun.  1983,  4:  807 
    Search in Google Scholar
  • 8b Kreuder W. Ringsdorf H. Tschirner P. Makromol. Chem., Rapid Commun.  1985,  6:  367 
    Search in Google Scholar
  • 8c Boden N. Bushby RJ. Cammidge AN. El-Mansoury A. Martin PS. Lu Z. J. Mater. Chem.  1999,  9:  1391 
    Search in Google Scholar
  • 8d Ji H. Zhao KQ. Yu WH. Wang BQ. Hu P. Sci. China, Ser. B  2009,  52:  75 
    Search in Google Scholar
  • 8e Zhao KQ. Bai YF. Hu P. Wang B. Mol. Cryst. Liq. Cryst.  2009,  509:  819 
    Search in Google Scholar
  • 9a Kumar S. Varshnay SK. Org. Lett.  2002,  4:  157 
    Search in Google Scholar
  • 9b Kumar S. Naidu JJ. Liq. Cryst.  2002,  29:  899 
    Search in Google Scholar
  • 10a Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed.  2001,  40:  2004 ; Angew. Chem. 2001, 113, 2056
    Search in Google Scholar
  • 10b Tornøe CW. Christensen C. Meldal M. J. Org. Chem.  2002,  67:  3057 
    Search in Google Scholar
  • 10c Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 ; Angew. Chem. 2002, 114, 2708
    Search in Google Scholar
  • 11 Pérez D. Guitián E. Chem. Soc. Rev.  2004,  33:  274 
    Search in Google Scholar
  • 12a Matheson IM. Musgrave OC. Webster CJ. J. Chem. Soc., Chem. Commun.  1965,  278 
  • 12b Boden N. Borner RC. Bushby RJ. Cammidge AN. Jesudason MV. Liq. Cryst.  1993,  15:  851 
    Search in Google Scholar
  • 12c Naarman H. Hanack M. Mattmer R. Synthesis  1994,  477 
  • 12d Kumar S. Manickam M. Chem. Commun.  1997,  1615 
  • 12e Cooke G. Sage V. Richomme T. Synth. Commun.  1999,  29:  1767 
    Search in Google Scholar
  • 12f Waldvogel SR. Wartini AR. Palle H. Rebek J. Tetrahedron Lett.  1999,  40:  3515 
    Search in Google Scholar
  • 12g Allen MT. Diele S. Harris KDS. Hegmann T. Kariuki BM. Lose D. Preece JE. Tschierke C. J. Mater. Chem.  2001,  11:  302 
    Search in Google Scholar
  • 12h Kumar S. Varshney SK. Synthesis  2001,  305 
  • 12i Schultz A. Laschat S. Morr M. Diele S. Dreyer M. Bringmann G. Helv. Chim. Acta  2002,  85:  3909 
    Search in Google Scholar
  • 12j Kong X. He Z. Gopee H. Jing X. Cammidge AN. Tetrahedron Lett.  2011,  52:  77 
    Search in Google Scholar
  • 13a

    We obtained 43% yield in our best trial for the synthesis of 6 instead of 94% as previously described by Kumar and Manickam.¹²d Moreover, Waldvogel¹³b has previously mentioned the similar impossibility to reproduce the yield described by Kumar and Manickam with the same procedure.

  • 13b Waldvogel SR. Synlett  2002,  622 
  • 14a Lessene G. Feldman KS. In Modern Arene Chemistry   Astruc D. Wiley-VCH; Weinheim: 2002.  p.479 
  • 14b Kramer B. Fröhlich R. Waldvogel SR. Eur. J. Org. Chem.  2003,  3549 
  • 15 Kumar S. Manickam M. Synthesis  1998,  1119 
  • 16 Kumar Gupta S. Raghunatan VA. Lakshminarayanan V. Kumar S. J. Phys. Chem. B  2009,  113:  12887 
    Search in Google Scholar
  • 18a Allen MT. Harris KDM. Kariuki MB. Kumari M. Preece JA. Diele S. Lose D. Hegmann C. Tschierske C. Liq. Cryst.  2000,  27:  689 
    Search in Google Scholar
  • 18b Pisula W. Tomovic Z. Simpson C. Kastler M. Pakula T. Müllen K. Chem. Mater.  2005,  17:  4296 
    Search in Google Scholar
  • 19 LoCoco MD. Zhang X. Jordan RF. J. Am. Chem. Soc.  2004,  126:  15231 
    Search in Google Scholar
  • 20 Demko PZ. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2110 
    Search in Google Scholar
  • 21a Stackhouse PJ. Hird M. Liq. Cryst.  2008,  35:  597 
    Search in Google Scholar
  • 21b Zhao B. Liu B. Png RQ. Zhang K. Lim KA. Luo J. Shao J. Ho PKH. Chi C. Wu J. Chem. Mater.  2010,  22:  435 
    Search in Google Scholar
17

We thank the referee for suggesting this explanation.