Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH16540
RESEARCH ARTICLE
Contents Vol 70(7)

Synthesis and Liquid Crystalline Properties of a New Homologous Series of 4,5-Disubstituted 2H-[1,2,3]-Triazoles via Azide-Chalcone Oxidative Cycloaddition Reaction

P. T. Sowmya A B and K. M. Lokanatha Rai A B
+ Author Affiliations
- Author Affiliations

A Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570006, India.

B Corresponding authors. Email: kmlrai@yahoo.com, ptsowmya8@gmail.com

Australian Journal of Chemistry 70(7) 764-768 https://doi.org/10.1071/CH16540
Submitted: 26 September 2016  Accepted: 5 December 2016   Published: 9 January 2017

Abstract

A new homologous series of 4,5-disubstituted 2H-[1,2,3]-triazole derivatives were synthesized from chalcones and sodium azide via oxidative cycloaddition reaction; CuI was used as catalyst. Flexibility in the synthesized molecules was provided by attaching straight alkoxy chains. The synthesized compounds were characterized by elemental analysis, and 1H NMR and 13C NMR and LC-MS spectroscopies . The stability and range of the mesophases increased with the length of the chain on the triazoles. The melting point, transition temperatures, and enantiotropic liquid crystal morphologies were determined by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) equipped with a hot stage.


References

[1]  M. Marcos, A. Omenat, J. L. Serrano, A. Ezcurra, Adv. Mater. 1992, 4, 285.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXitVeiurk%3D&md5=6c52db5ec511e7737e5a9d412b53c056CAS |

[2]  M. Hird, K. J. Toyne, G. W. Gray, Liq. Cryst. 1993, 14, 741.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXmvVarsrw%3D&md5=824c14ac4f139d6f2ead23ad0deea7e6CAS |

[3]  M. Hird, K. J. Toyne, G. W. Gray, S. E. Day, D. G. Mc Donnell, Liq. Cryst. 1993, 15, 123.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXitVSisw%3D%3D&md5=0ee3f5cd6bb512b2890db9bfa584a0d9CAS |

[4]     (a) G. W. Gray, P. A. Windsor, in Liquid Crystals and Plastic Crystals (Eds G. W. Gray, P. A. Windsor) 1974, Vol. 1, Ch. 4 (Ellis Horwood Ltd: Chichester)
         (b) G. W. Gray, Molecular Structure and the Properties of Liquid Crystal 1962 (Academic Press: London, New York).

[5]  H. Gallardo, I. Favarin, Liq. Cryst. 1993, 13, 115.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXhtlKkurs%3D&md5=0fcce318b265e53bb26a7aa22c6e608fCAS |

[6]  A. A. Vieira, F. R. Bryk, H. Gallardo, Tetrahedron Lett. 2009, 50, 905.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpsVWkuw%3D%3D&md5=ff1071af5f8eddc77342f37bd037573dCAS |

[7]  M. Tanaka, K. I. Takeharu, K. Kubo, A. Mori, Y. Fukazawa, Tetrahedron Lett. 2007, 63, 652.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlagtrrJ&md5=855b5ca151b41215cf479862abfa8d52CAS |

[8]  H. Gallardo, C. Zucco, Mol. Cryst. Liq. Cryst. 2002, 373, 181.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XlvFGqu7w%3D&md5=6215c6d3d3e57510cb02765acdb4d56cCAS |

[9]  V. N. Kovganko, N. N. Kovaganko, Russ. J. Org. Chem. 2006, 42, 696.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlvFWitr4%3D&md5=c76c538196fbe9e0f331f5f1cf9ac2e6CAS |

[10]  H. Gallardo, D. M. P de O. Santos, G. F. Caramori, F. Molin, I. H. Bechtold, Liq. Cryst. 2013, 40, 570.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjslKlt7s%3D&md5=0ecad4b24c261e8fec86c6395c2509eeCAS |

[11]  S. Roddecha, M. Anthamatten, Liq. Cryst. 2010, 37, 389.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXltFKntro%3D&md5=72d9577bf5d4cd31778d657a2758f748CAS |

[12]     (a) A. C. Tome, in Science of Synthesis (Eds R. C. Storr, T. L. Gilchrist) 2004, Vol 13, pp. 415–602 (Thieme: New York).
      (b) V. P. Krivopalov, O. P. Russ Shkurko, Russ. Chem. Rev. 2005, 74, 339.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  S. Velazquez, R. Alvarez, C. Perez, F. Gago, C. De, J. Balzarini, M. Camaraza, Antiviral Chem. Chemother. 1998, 9, 481.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DyaK1M%2Fot12jtw%3D%3D&md5=84ec320aa3e908b84f51bf7d5bfc8b70CAS |

[14]  C. Im, S. N. Maiti, R. G. Micetich, M. Daneshtalab, K. Atchson, O. A. Philips, J. Antibiot. 1994, 47, 1030.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmvVSntr4%3D&md5=0944646925da1c494ee83b2fadc9968fCAS |

[15]  S. Pålhagen, R. Canger, O. Henriksen, J. A. van Parys, M. E. Riviere, M. A. Karolchyk, Epilepsy Res. 2001, 43, 115.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  T. Duan, K. Fan, Y. Fu, C. Zhong, X. Chen, T. Peng, J. Qin, Dyes Pigm. 2012, 94, 28.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs1Kktr4%3D&md5=7c7fe64bdc2a1601568cb3f6f4590a5bCAS |

[17]  R. González-Olvera, V. Roman-Rodriguez, G. E. Negron-Silva, A. Espinoza-Vazquez, F. J. Rodriguez-Gomez, R. Santillan, Molecules 2016, 21, 250.
         | Crossref | GoogleScholarGoogle Scholar |

[18]     (a) W. Q. Fan, A. R. Katritzky, in Comprehensive Heterocyclic Chemistry II (Eds A. R. Katrizky, C. W. Rees, E. F. V. Scriven) 1996, Vol. 4, pp. 1–126. (Pergamon: New York, NY)
      (b) R. J. Willis, I. D. Marlow, Eur. Pat Appl. 400842 1990, . [Chem. Abstr. 1991, 114, 164247b].

[19]  G.-Y. Yeap, S. Balamurugan, M. V. Srinivas, P. Kannan, New J. Chem. 2013, 37, 1906.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXpsFahtrc%3D&md5=6b442b86a276be87d92f86bf9bc403fdCAS |

[20]  N. Gimeno, R. Martin-Rapun, S. Rodriguez-Conde, J. L. Serrano, C. L. Folcia, M. A. Pericas, M. B. Ros, J. Mater. Chem. 2012, 22, 16791.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFWmsr3P&md5=4e535db1f7a10d8482ecc9ae0d6cf5f0CAS |

[21]  K. C. Majumdar, S. Mondal, R. K. Sinha, New J. Chem. 2010, 34, 1255.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXos1ert74%3D&md5=eab3f751044d629ba5d643038c6b9c9dCAS |

[22]  Z. Cui, Y. Zhang, S. He, Colloid Polym. Sci. 2008, 286, 1553.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Wrs7jP&md5=fc7ee203f54b6b55065c81fcd6aa03bfCAS |

[23]  (a) H. Gallardo, A. J. Bortoluzzi, D. M. P. De Oliveira Santos, Liq. Cryst. 2008, 35, 719.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXotV2gsLc%3D&md5=bd341a74fe890479de9348c90d4089a3CAS |
      (b) A. Alshargabi, G.-Y. Yeap, A. K. M. Wan, C.-C. Han, H.-C. Lin, D. Takeuchi, Liq. Cryst. 2015, 42, 1337.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry (Ed. A. Padwa) 1984, pp. 516–518 (Wiley: New York, NY).

[25]  A. Hassner, K. M. L. Rai, Heterocycles 1990, 30, 817.
         | Crossref | GoogleScholarGoogle Scholar |

[26]  (a) Y. Zhang, X. Li, J. Li, J. Chen, X. Meng, M. Zhao, B. Chen, Org. Lett. 2012, 14, 26.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFGmtL7E&md5=223a2f7ede1a97e7e38bf0b9288bcb36CAS |
      (b) Y. R. Girish, K. S. S. Kumar, U. Muddegowda, N. K. Lokanath, K. S. Rangappa, S. Shashikanth, RSC Adv. 2014, 4, 55800.
         | Crossref | GoogleScholarGoogle Scholar |

[27]  Vogel’s Text Book of Practical Organic Chemistry, 4th edn 1978 (Longman Publishers: London, UK).

[28]  D. Demus, L. Richter, The Texture of Liquid Crystals 1978 (VEB Deutcher Verlag fur Grandstoff Industie: Leipzing).

[29]  P. J. Collings, M. Hird, Introduction to Liquid Crystals Chemistry and Physics 1997 (Taylor and Francis Ltd: London).

[30]  A. Seed, Chem. Soc. Rev. 2007, 36, 2046.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1Ghtb3M&md5=92ba057528a4a4a4072440febb7c4fe2CAS |

[31]  V. S. Bezborodov, C. J. Lee, K. H. Uh, in Sixth International Conference on Ferroelectric Liquid Crystals, Brest, France, 20–24 July. 1997; Conference Summaries, p. 152.