Synthesis and mesomorphic properties of 4,4”-dialkynyl-2’,3’-difluoro-p-terphenyls – the influence of C≡C acetylene linking bridge

References

• Kula P, Aptacy A, Herman J, et al. The synthesis and properties of fluoro-substituted analogues of 4-butyl-4’-[(4-butylphenyl)ethynyl] biphenyls. Liq Cryst. 2013;40:482–491.
   Web of Science ®Google Scholar
• Pytlarczyk M, Herman J, Harmata P, et al. The influence of the dialkylphenyltolane’s difluorosubstitution on mesomorphic and dielectric properties. Liq Cryst. 2018;45:1460–1469.
   Web of Science ®Google Scholar
• Dziaduszek J, Dąbrowski R, Urban S, et al. Selected fluorosubstituted phenyltolanes with a terminal group: NCS, CN, F, OCF3 and their mesogenic and dielectric properties and use for the formulation of high birefringence nematic mixtures to GHz and THz applications. Liq Cryst. 2017;44:1277–1292.
   Web of Science ®Google Scholar
• Herman J, Harmata P, Strzeżysz O, et al. Synthesis and properties of chosen 4-butyl-phenyltolane derivatives – on the influence of core substitution on birefringence, mesomorphic and dielectric properties. J Mol Liq. 2017. DOI:10.1016/j.molliq.2017.04.090
   Web of Science ®Google Scholar
• Herman J, Kula P. The synthesis of chiral fluorinated 4-alkyl-4’-[(4-alkylphenyl)ethynyl]biphenyls. Tetrahedron Lett. 2013;54:3621–3623.
   Web of Science ®Google Scholar
• Arakawa Y, Inui S, Tsuji H. Novel diphenylacetylene-based room-temperature liquid crystalline molecules with alkylthio groups, and investigation of the role for terminal alkyl chains in mesogenic incidence and tendency. Liq Cryst. 2018;45:811–820.
   Web of Science ®Google Scholar
• Li F, An Z, Chen X, et al. Synthesis and the effect of 2,3-difluoro substitution on the properties of diarylacetylene terminated by an allyloxy group. Liq Cryst. 2015;42:1654–1663.
   Web of Science ®Google Scholar
• Chen R, Zhao L, An Z, et al. Synthesis and properties of allyloxy-based tolane liquid crystals with high negative dielectric anisotropy. Liq Cryst. 2017;44:2184–2191.
   Web of Science ®Google Scholar
• Jung H, Yun JH, Jeon I, et al. Acetylene-containing highly birefringent rod-type reactive liquid crystals based on 2-methylhydroquinone. Liq Cryst. 2018;45:279–291.
   Web of Science ®Google Scholar
• Węgłowska D, Kula P, Herman J. High birefringence bistolane liquid crystals: synthesis and properties. RSC Adv. 2016;6:403–408.
   Web of Science ®Google Scholar
• Herman J, Kula P. Design of new super-high birefringent isothiocyanato bistolanes – synthesis and properties. Liq Cryst. 2017;44:1462–1467.
   Web of Science ®Google Scholar
• Gauza S, Wen CH, Wu ST, et al. Super high birefringence isothiocyanato biphenyl-bistolane liquid crystals. Jpn J Appl Phys. 2004;43:7634–7638.
   Web of Science ®Google Scholar
• Arakawa Y, Kang S, Nakajima S, et al. Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties. Liq Cryst. 2014;41:642–651.
   Web of Science ®Google Scholar
• Arakawa Y, Nakajima S, Ishige R, et al. Synthesis of diphenyl-diacetylene-based nematic liquid crystals and their high birefringence properties. J Mater Chem. 2012;22:8394–8398.
   Web of Science ®Google Scholar
• Chen R, An Z, Wang W, et al. Lateral substituent effects on UV stability of high-birefringence liquid crystals with the diaryl-diacetylene core: DFT/TD-DFT study. Liq Cryst. 2017;44:1515–1524.
   Web of Science ®Google Scholar
• Arakawa Y, Nakajima S, Kang S, et al. Synthesis and evaluation of dinaphthylacetylene nematic liquid crystals for high-birefringence materials. Liq Cryst. 2012;39:1063–1069.
   Web of Science ®Google Scholar
• Dąbrowski R, Kula P, Herman J. High birefringence liquid crystals. Crystals. 2013;3:443–482.
   Web of Science ®Google Scholar
• Neubert ME, Keast SS, Kim JM, et al. The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′‐disubstituted phenyl benzoates and phenyl thiobenzoates. Liq Cryst. 2005;32:247–265.
   Web of Science ®Google Scholar
• Srinivasa HT, Hariprasad S. Synthesis of some novel aromatic alkynylsilanes: mesomorphic characterization of ethynyl-substituted rod-shaped molecules. Mol Cryst Liq Cryst. 2014;588:17–27.
   Web of Science ®Google Scholar
• Gauza S, Dąbrowski R, Dziaduszek J, et al. Synthesis, mesomorphic properties and chemical stability of some fluoro terminally substituted acetylenes. Mol Cryst Liq Cryst. 1999;332:51–60.
   Web of Science ®Google Scholar
• Hird M, Toyne K, Gray GW. Palladium-catalysed cross-coupling reactions in the synthesis of somehigh polarizability materials. Liq Cryst. 1993;14:741–761.
   Web of Science ®Google Scholar
• Huang CC, Kao CC, Wang NC, et al. Antiferroelectric liquid crystals based on the salicylaldimine in connection with linear alkynyl chain. Liq Cryst. 2013;40:441–445.
   Web of Science ®Google Scholar
• Cho HJ, Seo K, Lee CJ, et al. Rod like mesogenic molecules consisting of two diacetylenic groups: mesomorphic behavior and photoimaging. J Mater Chem. 2003;13:986–990.
   Web of Science ®Google Scholar
• Schadt M, Buchecker R, Müller K. Invited Lecture. Material properties, structural relations with molecular ensembles and electro-optical performance of new bicyclohexane liquid crystals in field-effect liquid crystal displays. Liq Cryst. 1989;5:293–312.
   Web of Science ®Google Scholar
• Schadt M. Liquid crystal materials and liquid crystal displays. Annu Rev Mater Sci. 1997;27:305–379.
   Web of Science ®Google Scholar
• Schadt M. Liquid crystal displays, LC-materials and LPP photo-alignment. Mol Cryst Liq Cryst. 2017;647:253–268.
   Web of Science ®Google Scholar
• Schadt M. Nematic liquid crystals and twisted-nematic LCDs. Liq Cryst. 2015;42:646–652.
   Web of Science ®Google Scholar
• Jankowiak A, Ringstrand B, Januszko A, et al. Liquid crystals with negative dielectric anisotropy: the effect of unsaturation in the terminal chain on thermal and electro-optical properties. Liq Cryst. 2013;40:605–615.
   Web of Science ®Google Scholar
• Duffy WL, Jones JC, Kelly SM, et al. Novel nematic compounds incorporating two conjugated carbon-carbon double bonds in the terminal chain. Mol Cryst Liq Cryst. 1999;332:91–99.
   Web of Science ®Google Scholar
• Kelly SM, Germann A, Schadt M. The synthesis and liquid crystal transition temperatures of some weakly polar nematic methyl (E)-[trans-4-substituted-cyclohexyl]-allyl ethers. Liq Cryst. 1994;16:491–507.
   Web of Science ®Google Scholar
• Peng F, Huang Y, Gou F, et al. High performance liquid crystals for vehicle displays. Opt Mater Express. 2016;6:256002.
   Web of Science ®Google Scholar
• St W, Cs H, Yn C, et al. Fluorinated diphenyl-diacetylene and tolane liquid crystals with threshold voltage. Appl Phys Lett. 1992;61:2275–2277.
   Web of Science ®Google Scholar
• Wu ST, Neubert ME, Keast SS, et al. Wide nematic range alkenyl diphenyldiacetylene liquid crystals. Appl Phys Lett. 2000;77:957–959.
   Web of Science ®Google Scholar
• Gasowska JS, Cowling SJ, Cockett MCR, et al. The influence of an alkenyl terminal group on the mesomorphic behaviour and electro-optic properties of fluorinated terphenyl liquid crystals. J Mater Chem. 2010;20:299–307.
   Web of Science ®Google Scholar
• Yang F, Earl DJ. An all atom computer simulation study of the liquid crystalline phase behaviour of alkenic fluoroterphenyls. Soft Matter. 2011;7:10266–10273.
   Web of Science ®Google Scholar
• Gray GW, Hird M, Lacey D, et al. The synthesis and transition temperatures of some 4,4”-dialkyl-and 4,4”-alkoxyalkyl-1,1’:4’,1”-terphenyls with 2,3- or 2’,3’-difluoro substituents and of their biphenyl analogues. J Chem Soc Perkin Trans. 1989;II:2041–2053.
   Google Scholar
• Kula P, Spadło A, Dziaduszek J, et al. Mesomorphic, dielectric, and optical properties of fluorosubstituted biphenyls, terphenyls, and quatephenyls. Opto-Electron Rev. 2008;16:379–385.
   Web of Science ®Google Scholar
• Gauza S, Kula P, Liang X, et al. High birefringence and low viscosity liquid crystals with negative dielectric anisotropy. Mol Cryst Liq Cryst. 2009;509:47–59.
   Web of Science ®Google Scholar
• Li T, An Jun Q, A Z X, et al. Post-functionalization of disubstituted polyacetylenes via click chemistry. Sci China Chem. 2011;54:1954–1984.
   Web of Science ®Google Scholar
• Schimada T, Gb B, Yamamoto Y. Aquapalladium complex: A stable and convenient catalyst for the intermolecular hydroamination of alkynes. Eur J Org Chem. 2005;59–62.
   Web of Science ®Google Scholar
• Fujihara T, Tani Y, Semba K, et al. Copper-catalyzed silacarboxylation of internal alkynes by employing carbon dioxide and silylboranes. Angew Chem Int Ed. 2012;51:11487–11490.
   PubMed Web of Science ®Google Scholar
• Wang Y, Huang B, Sheng S, et al. A novel and efficient synthesis of terminal arylacetylenes via Sonogashira coupling reactions catalysed by MCM-41-supported bidentate phosphine palladium(0) complex. J Chem Res. 2007;12:728–732.
   Web of Science ®Google Scholar
• Kula P, Herman J, Pluczyk S, et al. Synthesis and mesomorphic properties of laterally substituted 4,4′′′-dialkyl-p-quaterphenyls. Liq Cryst. 2014;41:503–513.
   Web of Science ®Google Scholar