Skip to main content
SpringerLink
Log in

Synthesis of functionalized triphenylene discotic liquid crystals and the influence of unsaturated periphery on mesomorphism

  • Articles
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Twelve triphenylene discogens with unsaturated periphery (abbreviated as C18H6(OC5H11)6−x (OR) x (x = 1, 2, 3), R = -C3H6CH == CH2 (a), -C3H6C C ≡CH (b), -C2H4OCH== CH2 (c)) were synthesized and characterized. The thermotropic liquid crystal properties were studied by using polarized optical microscopy, differential scanning calorimetry and X-ray diffractometry. The results showed that all triphenylenes exhibited hexagonal columnar mesophase. The thermotropic studies showed that series a (alkene periphery) exhibited higher clearing points than the corresponding series b (alkyne periphery), while series c (vinyloxy periphery) exhibited highest clearing points and widest mesophase temperature ranges. We also found that the symmetric discogens sym-C18H6(OC5H11)3(OR)3 displayed higher melting points and clearing points than the asymmetric ones asym-C18H6(OC5H11)3(OR)3.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Kumar S. Self-organization of disc-like molecules: Chemical aspects. Chem Soc Rev, 2006, 35: 83–109

    Article  CAS  Google Scholar 

  2. Perez D, Guitian E. Selected strategies for the synthesis of triphenylenes. Chem Soc Rev, 2004, 33: 274–283

    Article  CAS  Google Scholar 

  3. Watson MD, Fechtenkotter A, Mullen K. Big is beautiful—“Aromaticity” revisited from the viewpoint of macromolecular and supramolecular benzene chemistry. Chem Rev, 2001, 101: 1267–1300

    Article  CAS  Google Scholar 

  4. Laschat S, Baro A, Steinke N, Giesselmann F, Hägele C, Scalia G, Judele R, Kapatsina E, Sauer S, Schreivogel A, Tosoni M. Discotic liquid crystals: From tailor-made synthesis to plastic electronics. Angew Chem Int Ed, 2007, 46: 4832–4887

    Article  CAS  Google Scholar 

  5. Sergeyev S, Pisula W, Geerts YH. Discotic liquid crystals: A new generation of organic semiconductors. Chem Soc Rev, 2007, 36: 1902–1929

    Article  CAS  Google Scholar 

  6. Shimizu Y, Oikawa K, Nakayama K, Guillon D. Mesophase semiconductors in field effect transistors. J Mater Chem, 2007, 17: 4223–4229

    Article  CAS  Google Scholar 

  7. Li LL, Hu P, Wang BQ, Yu WH, Shimizu Y, Zhao KQ. Synthesis and mesomorphism of ether-ester mixed tail C3-symmetrical truxene discotic liquid crystals. Liquid Cryst, 2010, 37: 499–506

    Article  Google Scholar 

  8. Zhao KQ, Chen C, Monobe H, Hu P, Wang B, Shimizu Y. Threechain truxene discotic liquid crystal showing high charged carrier mobility. Chem Commun, 2011, 47, 6290-6292

  9. Bushby RJ, Lozman OR. Discotic liquid crystals 25 years on. Curr Opin Colloid Interf Sci, 2002, 7: 343–354

    Article  CAS  Google Scholar 

  10. Hoeben FJM, Jonkheijm P, Meijer EW, Schenning APHJ. About supramolecular assemblies of pi-conjugated systems. Chem Rev, 2005, 105: 1491–1546

    Article  CAS  Google Scholar 

  11. Zhao KQ, Yu WH, Wang BQ, Hu P. Research progress in amide group hydrogen-bonding stabilized discotic liquid crystals. J Sichuan Normal Univ (Natural Science) (in Chinese), 2009, 32: 118–133

    CAS  Google Scholar 

  12. O’Neill M, Kelly SM. Ordered materials for organic electronics and photonics. Adv Mater, 2011, 23: 566–584

    Article  Google Scholar 

  13. Eichhorn H. Mesomorphic phthalocycanines, tetraazaporphyrins, porphyrins and triphenylenes as charged-transporting materials. J Porphyrins Phthalocyanines, 2000, 4: 88–102

    Article  CAS  Google Scholar 

  14. Bushby RJ, Lozman OR, Photoconducting liquid crystals. Curr Opin Solid State Mater Sci, 2002, 6: 569–578

    Article  CAS  Google Scholar 

  15. Adam D, Schuhmacher P, Simmerer J, Haussling L, Siemensmeyer K, Etzbach KH, Ringsdorf H, Haarer D. Fast photoconduction in the highly ordered columnar phase of a discotic liquid crystal. Nature, 1994, 371: 141–143

    Article  CAS  Google Scholar 

  16. Feng X, Marcon V, Pisula W, Hansen MR, Kirkpatrick J, Grozema F, Andrienko D, Kremer K, and Müllen K. Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics. Nature Mater, 2009, 8: 421–426

    Article  CAS  Google Scholar 

  17. Schmidt-Mende L, Fechtenkotter A, Mullen K, Moons E, Friend RH, MacKenzie JD. Self-organized discotic liquid crystals for high-efficiency organic photovoltaics. Science, 2001, 293: 1119–1122

    Article  CAS  Google Scholar 

  18. Kumar S. Recent developments in the chemistry of triphenylenebased discotic liquid crystals. Liquid Cryst, 2004, 31: 1037–1059

    Article  CAS  Google Scholar 

  19. Kumar S. Triphenylene-based discotic liquid crystal dimers, oligomers and polymers. Liquid Cryst, 2005, 32: 1089–1113

    Article  CAS  Google Scholar 

  20. Zhang L, Gopee H, Hughes DL, Cammidge AN. Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional π-overlap in the solid state. Chem Commun, 2010, 46: 4255–4257

    Article  CAS  Google Scholar 

  21. Kaller M, Deck C, Meister A, Hause G, Baro A, Laschate S. Counterion effects on the columnar mesophases of triphenylene-substituted [18]crown-6 ethers: Is flatter better? Chem Eur J, 2010, 16: 6326–6337

    Article  CAS  Google Scholar 

  22. Li J, He Z, Gopee H, Cammidge AN. Synthesis of crown ether-linked discotic triphenylenes. Org Lett, 2010, 12: 472–475

    Article  CAS  Google Scholar 

  23. Cammidge AN, Chausson C, Gopee H, Li J, Hughes DL. Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics. Chem Commun, 2009, 7375–7377

  24. Cammidge AN. The effect of size and shape variation in discotic liquid crystals based on triphenylene cores. Phil Trans R Soc A, 2006, 364: 2697–2708

    Article  CAS  Google Scholar 

  25. Cammidge AN, Gopee H. Synthesis and liquid crystal properties of mixed alkynyl-alkoxy-triphenylenes. Liquid Cryst, 2009, 36: 809–816

    Article  CAS  Google Scholar 

  26. Miao J, Zhu L. Hydrogen bond-assisted supramolecular self-assembly of doubly discotic supermolecules based on porphyrin and triphenylene. Chem Mater, 2010, 22: 197–206

    Article  CAS  Google Scholar 

  27. Yu WH, Zhao KQ, Wang BQ, Hu P. Synthesis and mesomorphism of hydrogen-bonding stabilized triphenylene discotic liquid crystals. Acta Chim Sinica (in Chinese), 2007, 65: 1140–1148

    CAS  Google Scholar 

  28. Zhao KQ, Gao CY, Hu P, Wang BQ, Li Q. Synthesis of triphenylene discotic liquid crystals substituted with ester or amide functional groups and the effect of hydrogen bonding on mesogenic behaviors. Acta Chim Sinica (in Chinese), 2006, 64: 1051–1062

    CAS  Google Scholar 

  29. Miyake Y, Hu P, Zhao KQ, Monobe H, Fujii A, Ozaki M, Shimizu Y. Carrier mobility behavior of triphenylene mesogen with a hydrogen bonding amide group. Mol Cryst Liquid Cryst, 2010, 525: 97–103

    Article  CAS  Google Scholar 

  30. Mahoney SJ, Ahmida MM, Kayal H, Fox N, Shimizu Y, Eichhorn SH. Synthesis, mesomorphism and electronic properties of nonaflate and cyano-substituted pentyloxy and 3-methylbutyloxy triphenylenes. J Mater Chem, 2009, 19: 9221–9232

    Article  CAS  Google Scholar 

  31. Chen HM, Zhao KQ, Wang L, Hu Ping, Wang BQ. Synthesis and mesomorphism of triphenylene discotic liquid crystals containing fluorinated chains. Soft Mater, 2011, 9: 359–381

    Article  CAS  Google Scholar 

  32. Yang GF, Zhao KQ, Yu WH, Hu P, Wang BQ. Synthesis of unsymmetric triphenylene discotic liquid crystals with a semi-fluorinated chain and the influence of fluorophobic effect on mesogenic behavior. Sci China Ser B: Chem, 2009, 52(8): 1244–1252

    Article  CAS  Google Scholar 

  33. Yu W, Nie SC, Bai YF, Jing Y, Wang BQ, Hu P, Zhao KQ. Synthesis of disk-rod-disk liquid crystal trimers by using click chemistry. Sci China Chem, 2010, 53(5): 1134–1141

    Article  CAS  Google Scholar 

  34. Ji H, Zhao KQ, Yu WH, Wang BQ, Hu P. Synthesis and mesomorphism of diacetylene-bridged triphenylene discotic liquid crystal dimers. Sci China Ser B: Chem, 2009, 52: 975–985

    Article  CAS  Google Scholar 

  35. Xing CM, Lam JWY, Zhao KQ, Tang BZ. Synthesis and liquid crystalline properties of poly(1-alkyne)s carrying triphenylene discogens. J Polym Sci Polym Chem, 2008, 46: 2960–2974

    Article  CAS  Google Scholar 

  36. Cammidge AN, Beddall AR, Gopee H. Unexpected mesophase behaviour in novel triphenylene multi-alkenes. Tetrahedron Lett, 2007, 48: 6700–6703

    Article  CAS  Google Scholar 

  37. Schulte JL, Laschat S, Vill V, Nishikawa E, Finkelmann H, Nimtz M. Convergent synthesis of columnar twins and tetramers from triphenylene building blocks—The first example of a columnar spiro-twin. Eur J Org Chem, 1998, 2499–2506

  38. Bai YF, Zhao KQ, Hu P, Wang BQ, Shimizu Y. Synthesis of amide group containing triphenylene derivatives as discotic liquid crystals and organic gelators. Mol Cryst Liquid Cryst, 2009, 509: 60–76

    Article  Google Scholar 

  39. Zhao KQ, Wang BQ, Hu P, Li Q, Zhang LF. Synthesis of new triphenylene-containing discotic liquid crystals and the influence of fluorophilic effect and molecular symmetry on mesomorphism. Chin J Chem, 2005, 23(6), 767–774

    Article  CAS  Google Scholar 

  40. Zhao KQ, Wang BQ, Hu P, Gao CY, Yuan FJ, Li HR. New triphenylene based discotic liquid crystals with mixed tails: molecular symmetry and wide columnar mesophase range. Chin J Chem, 2006, 24, 210–214

    Article  CAS  Google Scholar 

  41. Zhao KQ, Hu P, Wang BQ, Yu WH, Chen HM, Wang XL, Shimizu Y. Synthesis of mixed tail triphenylene discotic liquid crystals: Molecular symmetry and oxygen-atom effect on stabilization of columnar mesophases. Chin J Chem, 2007, 25: 375–381

    Article  CAS  Google Scholar 

  42. Dierking I. Textures of Liquid Crystals. Weinheim: Wiley-VCH, 2003

    Book  Google Scholar 

  43. Ding FJ, Zhao KQ. Study on clear points of triphenylene discotic liquid crystals with vinyloxy peripheral chains by mean field theory. Acta Chem Sinica (in Chinese), 2009, 67: 2290–2294

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610066, China

    KeQing Zhao, Hui Zhou, WenHao Yu, Ping Hu & BiQin Wang

  2. National Institute of Advanced Industrial Science and Technology, Kansai Centre, Midorigaoka, Ikeda, Osaka, 563-8577, Japan

    Hirosato Monobe & Yo Shimizu

Authors
  1. KeQing Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hui Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. WenHao Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ping Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. BiQin Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hirosato Monobe
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yo Shimizu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to KeQing Zhao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhao, K., Zhou, H., Yu, W. et al. Synthesis of functionalized triphenylene discotic liquid crystals and the influence of unsaturated periphery on mesomorphism. Sci. China Chem. 54, 1576–1583 (2011). https://doi.org/10.1007/s11426-011-4325-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-011-4325-8

Keywords

Search

Navigation