Acetylene-bridged triazine π-conjugated structures: synthesis and liquid crystalline properties

Acetylene-bridged triazine π-conjugated structures: synthesis and liquid crystalline properties

We report the synthesis and liquid crystalline properties of a new type of tribranched compound built up fromtriazine as the central core and electron-rich triazine rings as peripheral groups. An equimolar mixture of the star-shapedcompound based on the 1,3,5-triazine core with 4-dodecyloxybenzoic acid produced an organic salt exhibiting a columnarmesophase with a dendritic growing texture at low temperatures. The liquid crystalline properties of the triazine-basedcompound and organic salt were investigated by differential scanning calorimetry and polarizing optical microscopy.

___

  • 1. Vlad-Bubulak T, Buchs J, Kohlmeier A, Bruma M, Janietz D. Mesophase morphologies of hydrogen-bonded complexes of biphenyl-substituted diamino-1,3,5-triazines with semiperfluorinated benzoic acids. Chemistry of Materials 2007; 19 (18): 4460-4466. doi: 10.1021/cm070909h
  • 2. Leslie E. Liquid Crystals: The Science and Art of a Fluid Form. Chicago, IL, USA: University of Chicago Press, 2016.
  • 3. Lee H, Kim D, Lee HK, Qiu W, Oh NK et al. Discotic liquid crystalline materials for potential nonlinear optical applications: synthesis and liquid crystalline behavior of 1, 3, 5-triphenyl-2, 4, 6-triazine derivatives containing achiral and chiral alkyl chains at the periphery. Tetrahedron Letters 2004; 45 (5): 1019-1022. doi: 10.1016/j.tetlet.2003.11.085
  • 4. Holst HC, Pakula T, Meier H. Liquid crystals in the series of 2, 4, 6-tristyryl-1, 3, 5-triazines. Tetrahedron 2004; 60 (32): 6765-6775. doi: 10.1016/j.tet.2004.06.031
  • 5. Meier H, Lehmann M, Holst HC, Schwöppe D. Star-shaped conjugated compounds forming nematic discotic systems. Tetrahedron 2004; 60 (32): 6881-6888. doi: 10.1016/j.tet.2004.06.031
  • 6. Yao DS, Zhang BY, Zhang WW, Tian M. A new class of star-shaped cholesteric liquid crystal containing a 1, 3, 5- trihydroxybenzene unit as a core. Journal of Molecular Structure 2008; 881 (1-3): 83-89. doi: 10.1016/j.molstruc.2007.08.041
  • 7. Chen L, Chen YW, Yao K, Zhou WH, Li F et al. Synthesis and helical conformation of new optically active liquid crystalline polythiophene containing cyanoterphenyl mesogen pendant. Acta Physico-Chimica Sinica 2010; 26 (4): 971-980.
  • 8. Kumar S, Gupta SK. Novel triphenylenoimidazole discotic liquid crystals. Tetrahedron Letters 2011; 52 (41): 5363-5367. doi: 10.1016/j.tetlet.2011.08.041
  • 9. Miniewicz A, Gniewek A, Parka J. Liquid crystals for photonic applications. Optical Materials 2003; 21 (1-3): 605-610. doi: 10.1016/S0925-3467(02)00209-4
  • 10. Kumar S. Recent developments in the chemistry of triphenylene-based discotic liquid crystals. Liquid Crystals 2004; 31 (8): 1037-1059. doi: 10.1080/02678290410001724746
  • 11. Yeh P, Gu C. Optics of Liquid Crystal Displays (Vol. 67). New York, NY, USA: John Wiley & Sons, 2010.
  • 12. Binnemans K. Ionic liquid crystals. Chemical Reviews 2005; 105: 4148-4204. doi: 10.1021/cr0400919
  • 13. Staatz I, Granzer UH, Blume A, Roth HJ. Syntheses und Aggregationsverhalten chiraler Cystein-Amphiphile mitsTriazin als verknüpfende Partialstruktur Liebigs Annalen der Chemie 1989; (2): 127-131. doi: 10.1002/jlac.198919890126
  • 14. Zhang H, Jakisch L, Komber H, Voita B, Bohme F. Synthesis of multifunctional coupling agents and their selective reactions with hydroxy and amino groups in the melt Tetrahedron 2013; (69): 3656-3663. doi: 10.1016/j.tet.2013.03.024
  • 15. Türkçü HN, Ocak H, Gürbüz MU, Çakar F, Bilgin-Eran B et al. A study of dendritic ionic liquid crystals: using (S)-4-citronellyloxybenzoic acid and polypropylene imine dendrimers. Journal of Molecular Liquids 2016; 216: 209-215. doi: 10.1016/j.molliq.2015.12.070
  • 16. Kumar CRS, Jha A, Sastry SS. Induced crystal G phase of liquid crystalline amide through inter molecular hydrogen bonding. Journal of Non-Crystalline Solids 2010; 356: 334-339. doi:10.1016/j.jnoncrysol.2009.11.036
  • 17. Pisupati S, Kumar PA, Pisipati VGKM. Induced crystal G phase through intermolecular hydrogen bonding II. Influence of alkyl chain length of n-alkyl p-hydroxybenzoates on thermal and phase behavior. Liquid Crystals, 2000; 27 (5): 665-669. doi: 10.1080/026782900202525
  • 18. Stackhouse PJ, Wilson A, Lacey D, Hird M. Synthesis and properties of novel columnar liquid crystals based on symmetrical and non-symmetrical 1,3,5-trisubstituted benzene derivatives. Liquid Crystals 2010; 37 (9): 1191-1203. doi: 10.1080/02678292.2010.490647
  • 19. Kumar S. Self-organization of disc-like molecules: chemical aspects. Chemical Society Reviews 2006; 35: 83-109. doi: 10.1039/B506619K
  • 20. Kumar S. Playing with discs. Liquid Crystals 2009; 36: 607-638. doi: 10.1080/02678290902755549
  • 21. Kotha S, Kashinath D, Kumar S. Synthesis of liquid crystalline materials based on 1,3,5-triphenylbenzene and 2,4,6-triphenyl-1,3,5-s-triazine. Tetrahedron Letters 2008; 49: 5419-5423. doi: 10.1016/j.tetlet.2008.07.021
  • 22. Majumdara KC, Dea N, Roya B, Bhaumi A. Synthesis and mesophase characterisation of a series of new triazinebased disc-shaped molecules. Liquid Crystals 2010; 37: 1459-1464. doi: 10.1080/02678292.2010.520750
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK