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Original Articles

Synthesis of luminescent liquid crystals derived from gallic acid containing heterocyclic 1,3,4-oxadiazole

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Pages 1162-1172 | Received 05 Dec 2013, Accepted 26 Mar 2014, Published online: 24 Apr 2014

References

  • Seed A. Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core. Chem Soc Rev. 2007;36:2046–2069. doi:10.1039/b612666a
  • Meyer E, Zucco C, Gallardo H. Metallomesogens: synthesis and properties. J Mater Chem. 1998;8:1351–1354. doi:10.1039/a801159a
  • Bartulin J, Martinez R, Gallardo H, Muller J, Taylor TR. Synthesis and mesomorphic properties of 3,5-bis-(p-n-alkoxyphenyl)lsoxazole and 3,5-bis-(p-n-alkoxyphenyl)pyrazole. Mol Cryst Liq Crys A. 1993;225:175–182. doi:10.1080/10587259308036227
  • Gallardo H, Zucco C, Da Silva L. Synthesis and characterization of a new series of liquid crystal compounds derived from isoxazoles. Mol Cryst Liq Cryst. 2002;373:181–190. doi:10.1080/10587250210533
  • Gallardo H, Magnago R, Bortoluzzi AJ. Synthesis, characterization and mesomorphic properties of Ag(I) and Pd(II) complexes containing the pyridyl and tetrazoyl rings: crystal structure of [C30H46N10Ag ClO4]. Liq Cryst. 2001;28:1343–1352. doi:10.1080/02678290110066813
  • Vlachos P, Mansoor B, Aldred MP, O’Neill M, Kelly SM. Charge-transport in crystalline organic semiconductors with liquid crystalline order. Chem Commun. 2005;2921–2923. doi:10.1039/b501875g
  • Shirota Y. Organic materials for electronic and optoelectronic devices. J Mater Chem. 2000;10:1–25. doi:10.1039/a908130e
  • Parra M, Alderete J, Zuńñiga C, Gallardo H, Hidalgo P, Vergara J, Hernandez S. Azo compounds and Schiff ’s bases derived from 5-(4-pyridyl)-2-amino-1,3,4-thiadiazole: synthesis, mesomorphic properties and structural study by semi-empirical calculations. Liq Cryst. 2001;28:1659–1666. doi:10.1080/02678290110071565
  • Adachi C, Tsutsui T, Saito S. Organic electroluminescent device having a hole conductor as an emitting layer. Appl Phys Lett. 1989;55:1489–1491. doi:10.1063/1.101586
  • Wu F-I, Shu C-F, Chien C-H, Tao Y-T. Fluorene-based oxadiazoles: thermally stable electron-transporting materials for light-emitting devices. Synthetic Met. 2005;148:133–139. doi:10.1016/j.synthmet.2004.09.029
  • Wook Cha S, Choi S-H, Kim K, Jin J-I. Synthesis and luminescence properties of four-armed conjugated structures containing 1,3,4-oxadiazole moietiesElectronic supplementary information (ESI) available: synthesis details. See http://www.rsc.org/suppdata/jm/b3/b302568c/. J Mater Chem. 2003;13:1900–1904. doi:10.1039/b302568c
  • Wang C, Jung G-Y, Hua Y, Pearson C, Bryce MR, Petty MC, Batsanov AS, Goeta AE, Howard JAK. An efficient pyridine- and oxadiazole-containing hole-blocking material for organic light-emitting diodes:  synthesis, crystal structure, and device performance. Chem Mater. 2001;13:1167–1173. doi:10.1021/cm0010250
  • Xu Z, Li Y, Ma X, Gao X, Tian H. Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives. Tetrahedron. 2008;64:1860–1867. doi:10.1016/j.tet.2007.11.099
  • Sung H-H, Lin H-C. Effect of polar substituents on the properties of 1,3,4-oxadiazole-based liquid crystalline materials containing asymmetric cores. Liq Cryst. 2004;31:831–840. doi:10.1080/02678290410001703109
  • Cristiano R, Santos DMPdO, Gallardo H. Synthesis and characterization of low molecular mass luminescent liquid crystalline materials with 1,3,4‐oxadiazole units. Liq Cryst. 2005;32:7–14. doi:10.1080/02678290412331329288
  • Wen C-R, Wang Y-J, Wang H-C, Sheu H-S, Lee G-H, Lai CK. Columnar metallomesogens derived from 1,3,4-Oxadiazoles and X-ray crystal structure of dichlorobis[2,5-bis(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole]palladium(II). Chem Mater. 2005;17:1646–1654. doi:10.1021/cm0483691
  • Zhang Y-D, Jespersen KG, Kempe M, Kornfield JA, Barlow S, Kippelen B, Marder SR. Columnar discotic liquid-crystalline oxadiazoles as electron-transport materials. Langmuir. 2003;19:6534–6536. doi:10.1021/la0341456
  • Cristiano R, Ely F, Gallardo H. Light‐emitting bent‐shape liquid crystals. Liq Cryst. 2005;32:15–25. doi:10.1080/02678290412331329279
  • Wang H, Zheng Z, Shen D. Blue phase liquid crystals induced by bent-shaped molecules based on 1,3,4-oxadiazole derivatives. Liq Cryst. 2012;39:99–103. doi:10.1080/02678292.2011.628704
  • Belaissaoui A, Cowling SJ, Goodby JW. Mesogenic properties of two 1,3,4-oxadiazole-based bent-core geometrical isomers. Liq Cryst. 2013;40:421–427. doi:10.1080/02678292.2012.755226
  • Yang X, Dai H, He Q, Tang J, Cheng X, Prehm M, Tschierske C. Hexagonal columnar mesophases of polycatenar para-phenylene connected bis-oxadiazole-based liquid crystals. Liq Cryst. 2013;40:1028–1034. doi:10.1080/02678292.2013.803617
  • Cristiano R, Vieira AA, Ely F, Gallardo H. Synthesis and characterization of luminescent hockey stick‐shaped liquid crystalline compounds. Liq Cryst. 2006;33:381–390. doi:10.1080/02678290500483304
  • Gallardo H, Cristiano R, Vieira AA, Neves Filho RAW, Srivastava RM. Sonogashira coupling applied in the synthesis of 1,2,4-oxadiazole-based nonsymmetrical liquid crystals. Synthesis. 2008;2008:605–609. doi:10.1055/s-2008-1032156
  • Lai CK, Ke Y-C, Chien-Shen J-C J.S., Li W-R. Heterocyclic 1,3,4-oxadiazole as columnar core. Liq Cryst. 2002;29:915–920. doi:10.1080/02678290210129957
  • Frizon TE, Rampon DS, Gallardo H, Merlo AA, Schneider PH, Rodrigues OED, Braga AL. Selenides and diselenides containing oxadiazoles: a new class of functionalised materials. Liq Cryst. 2012;39:769–777. doi:10.1080/02678292.2012.680505
  • Gallardo H, Bryk FR, Vieira AA, Frizon TE, Conte G, Souza BS, Eccher J, Bechtold IH. Optical and thermal properties of unsymmetrical liquid crystalline compounds based on isoxazole. Liq Cryst. 2009;36:839–845. doi:10.1080/02678290903072035
  • Cristiano R, Gallardo H, Bortoluzzi AJ, Bechtold IH, Campos CEM, Longo RL. Tristriazolotriazines: a core for luminescent discotic liquid crystals. Chem Commun. 2008;5134–5136. doi:10.1039/b810680k
  • Hersmis MC, Spiering AJH, Waterval RJM, Meuldijk J, Vekemans JAJM, Hulshof LA. 3,4,5-Tri-dodecyloxybenzoic acid: optimisation and scale-up of the synthesis. Org Process Res Dev. 2001;5:54–60. doi:10.1021/op000066e
  • Hill J. 4.23–1,3,4-Oxadiazoles. In: Katritzky AR, Rees CW, editors. Comprehensive heterocyclic chemistry. Oxford: Pergamon; 1984. p. 427–446.
  • Seo SH, Park JH, Tew GN, Chang JY. Thermotropic liquid crystals of 1H-imidazole amphiphiles showing hexagonal columnar and micellar cubic phases. Tetrahedron Lett. 2007;48:6839–6844. doi:10.1016/j.tetlet.2007.07.187
  • Bechtold IH, Eccher J, Faria GC, Gallardo H, Molin F, Gobo NRS, de Oliveira KT, von Seggern H. New columnar Zn-phthalocyanine designed for electronic applications. J Phys Chem B. 2012;116:13554–13560. doi:10.1021/jp307825u
  • 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 Edit. 2007;46:4832–4887. doi:10.1002/anie.200604203
  • Lam JWY, Kong X, Dong Y, Cheuk KKL, Xu K, Tang BZ. Synthesis and properties of liquid crystalline polyacetylenes with different spacer lengths and bridge orientations. Macromolecules. 2000;33:5027–5040. doi:10.1021/ma992097j

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