1,3,5-Triazine(trithiophenylcarboxylate) esters form metastable monotropic nematic discotic liquid crystal phases

References

• Sergeyev S, Pisula W, Geerts YH. Discotic liquid crystals: a new generation of organic semiconductors. Chem Soc Rev. 2007;36(12):1902–1929.
   PubMed Web of Science ®Google Scholar
• Laschat S, Baro A, Steinke N, et al. Discotic liquid crystals: from tailor-made synthesis to plastic electronics. Angew Chem Int Ed. 2007;46(26):4832–4887.
   PubMed Web of Science ®Google Scholar
• Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116(3):1139–1241.
   PubMed Web of Science ®Google Scholar
• Kumar S. Chemistry of discotic liquid crystals: from monomers to polymers. Boca Raton (FL): CRC Press; 2010.
   Google Scholar
• Bisoyi HK, Kumar S. Discotic nematic liquid crystals: science and technology. Chem Soc Rev. 2010;39(1):264–285.
   PubMed Web of Science ®Google Scholar
• Olate FA, Ulloa JA, Vergara JM, et al. Columnar liquid crystalline tris-(ether)triazines with pendant 1,3,4-thiadiazole groups: synthesis, mesomorphic, luminescence, solvatofluorochromic and electrochemical properties. Liq Cryst. 2016;43(6):811–827.
   Web of Science ®Google Scholar
• Olate FA, Parra ML, Vergara JM, et al. Star-shaped molecules as functional materials based on 1,3,5-benzenetriesters with pendant 1,3,4-thiadiazole groups: liquid crystals, optical, solvatofluorochromic and electrochemical properties. Liq Cryst. 2017;44(7):1173–1184.
   Web of Science ®Google Scholar
• Geng Y, Fechtenkötter A, Müllen K. Star-like substituted hexaarylbenzenes: synthesis and mesomorphic properties. J Mater Chem. 2001;11(6):1634–1641.
   Web of Science ®Google Scholar
• Meier H, Lehmann M, Holst HC, et al. Star-shaped conjugated compounds forming nematic discotic systems. Tetrahedron. 2004;60(32):6881–6888.
   Web of Science ®Google Scholar
• Hindmarsh P, Hird M, Styring P, et al. Lateral substitution in the peripheral moieties of triphenylen-2,3,6,7,10,11-hexayl hexakis(4-alkoxybenzoate)s: dimethyl-substituted systems. J Mater Chem. 1993;3(11):1117–1128.
   Web of Science ®Google Scholar
• Kumar S, Varshney SK. Design and synthesis of discotic nematic liquid crystals. Org Lett. 2002;4(2):157–159.
   PubMed Web of Science ®Google Scholar
• Kohmoto S, Mori E, Kishikawa K. Room-temperature discotic nematic liquid crystals over a wide temperature range: alkali-metal-ion-induced phase transition from discotic nematic to columnar phases. J Am Chem Soc. 2007;129(44):13364–13365.
   PubMed Web of Science ®Google Scholar
• Chen -H-H, Lin H-A, Chien S-C, et al. Single-component room-temperature discotic nematic liquid crystals formed by introducing an attraction-enhancing in-plane protrusion onto the hexa(phenylethynyl)benzene core. J Mater Chem. 2012;22(25):12718–12722.
   Web of Science ®Google Scholar
• Gupta M, Gupta SP, Mohapatra SS, et al. Room-temperature oligomeric discotic nematic liquid crystals over a wide temperature range: structure–property relationships. Chem – Eur J. 2017;23(44):10626–10631.
   PubMed Web of Science ®Google Scholar
• Langner M, Praefcke K, Krüerke D, et al. Chiral radial pentaynes exhibiting cholesteric discotic phases. J Mater Chem. 1995;5(4):693–699.
   Web of Science ®Google Scholar
• Kumar S, Varshney SK. A room-temperature discotic nematic liquid crystal. Angew Chem Int Ed. 2000;39(17):3140–3142.
   PubMed Web of Science ®Google Scholar
• Zhang J, Moore JS. Nanoarchitectures. 6. Liquid crystals based on shape-persistent macrocyclic mesogens. J Am Chem Soc. 1994;116(6):2655–2656.
   Web of Science ®Google Scholar
• Seo SH, Jones TV, Seyler H, et al. Liquid crystalline order from ortho-phenylene ethynylene macrocycles. J Am Chem Soc. 2006;128(29):9264–9265.
   PubMed Web of Science ®Google Scholar
• Zhang L, Gopee H, Hughes DL, et al. Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional π-overlap in the solid state. Chem Commun. 2010;46(24):4255–4257.
   PubMed Web of Science ®Google Scholar
• Zhang L, Hughes DL, Cammidge AN. Discotic triphenylene twins linked through thiophene bridges: controlling nematic behavior in an intriguing class of functional organic materials. J Org Chem. 2012;77(9):4288–4297.
   PubMed Web of Science ®Google Scholar
• Kirres J, Schmitt K, Wurzbach I, et al. Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents. Org Chem Front. 2017;4(5):790–803.
   Web of Science ®Google Scholar
• Schultz A, Laschat S, Saipa A, et al. Columnar liquid crystals with a central crown ether unit. Adv Funct Mater. 2004;14(2):163–168.
   Web of Science ®Google Scholar
• Hassheider T, Benning SA, Kitzerow H-S, et al. Color-tuned electroluminescence from columnar liquid crystalline alkyl arenecarboxylates. Angew Chem Int Ed. 2001;40(11):2060–2063.
   PubMed Web of Science ®Google Scholar
• Bock H, Babeau A, Seguy I, et al. Electron-deficient columnar plastic crystals. Chem Phys Chem. 2002;3(6):532–535.
   Web of Science ®Google Scholar
• Kim BG, Kim S, Park SY. Star-shaped discotic nematic liquid crystal containing 1,3,5-triethynylbenzene and oxadiazole-based rigid arms. Tetrahedron Lett. 2001;42(14):2697–2699.
   Web of Science ®Google Scholar
• Lee JH. Supramolecular discotic nematic liquid crystals built through simple hydrogen bonding between 1,3,5-tris(4-hydroxyphenyl)benzene and stilbazole derivatives. Mol Cryst Liq Cryst. 2016;635(1):133–138.
   Web of Science ®Google Scholar
• Reilly MK, King RP, Wagner AJ, et al. Microwave-assisted esterification: a discovery-based microscale laboratory experiment. J Chem Educ. 2014;91(10):1706–1709.
   Web of Science ®Google Scholar
• Leriche P. Star-shaped triazine–thiophene conjugated systems. Tetrahedron Lett. 2009;50(40):5673–5676.
   Web of Science ®Google Scholar