Synthesis and characterisation of imidazolium-based ionic liquid crystals bearing a cholesteryl mesogenic group

References

• Zakrzewska ME, Bogel-Łukasik E, Bogel-Łukasik R. Ionic liquid-mediated formation of 5-hydroxymethylfurfural—a promising biomass-derived building block. Chem Rev. 2011;111:397–417. doi:10.1021/cr100171a.
   PubMed Web of Science ®Google Scholar
• Aoun B, Gonzalez MA, Ollivier J, Russina M, Izaola Z, Price DL, Saboungi ML. Translational and reorientational dynamics of an imidazolium-based ionic liquid. J Phys Chem Lett. 2010;1:2503–2507. doi:10.1021/jz100856t.
   Web of Science ®Google Scholar
• Holbrey JD, Seddon KR, Wareing RA. A simple colorimetric method for the quality control of 1-alkyl-3-methylimidazolium ionic liquid precursors. Green Chem. 2001;3:33–36. doi:10.1039/b009459p.
   Web of Science ®Google Scholar
• Dupont J, de Souza RF, Suarez PAZ. Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev. 2002;102:3667–3692. doi:10.1021/cr010338r.
   PubMed Web of Science ®Google Scholar
• Mallakpour S, Rafiee Z. Ionic liquids as environmentally friendly solvents in macromolecules chemistry and technology, Part I. J Polym Environ. 2011;19:447–484. doi:10.1007/s10924-011-0287-3.
   Web of Science ®Google Scholar
• Mallakpour S, Rafiee Z. Ionic liquids as environmentally friendly solvents in macromolecules chemistry and technology, Part II. J Polym Environ. 2011;19:485–517. doi:10.1007/s10924-011-0291-7.
   Web of Science ®Google Scholar
• Hoarfrost ML, Segalman RA. Conductivity scaling relationships for nanostructured block copolymer/ionic liquid membranes. ACS Macro Lett. 2012;1:937–943. doi:10.1021/mz300241g.
   PubMed Web of Science ®Google Scholar
• Ocak H, Bilgin-Eran B, Prehm M, Tschierske C. Effects of molecular chirality on superstructural chirality in liquid crystalline dark conglomerate phases. Soft Matter. 2012;8:7773–3783. doi:10.1039/c2sm25763g.
   Web of Science ®Google Scholar
• Archer P, Dierking I. Chirality enhancement through addition of achiral molecules. Chem Commun. 2010;46:1467–1469. doi:10.1039/b915567h.
   PubMed Web of Science ®Google Scholar
• Vijayaraghavan RK, Abraham S, Rao DSS, Prasad SK, Das S. Light induced generation of stable blue phase in photoresponsive diphenylbutadiene based mesogen. Chem Commun. 2010;46:2796–2798. doi:10.1039/b926524d.
   PubMed Web of Science ®Google Scholar
• Binnemans K. Ionic liquid crystals. Chem Rev. 2005;105:4148–4204. doi:10.1021/cr0400919.
   PubMed Web of Science ®Google Scholar
• Amann T, Dold C, Kailer A. Rheological characterization of ionic liquids and ionic liquid crystals with promising tribological performance. Soft Matter. 2012;8:9840–9846. doi:10.1039/c2sm26030a.
   Web of Science ®Google Scholar
• Yang M, Stappert K, Mudring AV. Bis-cationic ionic liquid crystals. J Mater Chem C. 2014;2:458–473. doi:10.1039/c3tc31368a.
   Web of Science ®Google Scholar
• Starkulla GF, Klenk S, Butschies M, Tussetschlager S, Laschat S. Towards room temperature ionic liquid crystals: linear versus bent imidazolium phenylpyrimidines. J Mater Chem. 2012;22:21987–21997. doi:10.1039/c2jm34595a.
   Web of Science ®Google Scholar
• Li C, He J, Chen J, Liu J, Zhang Q, Yu Z. Ionic liquid crystalline phases in 3-hexadecylimidazolium bromide and binary mixtures with 1-decanol. J Colloid Interface Sci. 2011;359:474–480. doi:10.1016/j.jcis.2011.04.014.
   PubMed Web of Science ®Google Scholar
• Hessel V, Ringsdorf H, Festag R, Wendorff JH. Ionic thermotropic liquid crystals formed by monomeric dipolar and polymeric multipolar amphiphiles with pyridinium head groups. Makromol Chem Rapid Commun. 1993;14:707–718. doi:10.1002/marc.1993.030141105.
   Google Scholar
• Sanchez I, Campo JA, Heras JV, Torresb MR, Cano M. Pyrazolium salts as a new class of ionic liquid crystals. J Mater Chem. 2012;22:13239–13251. doi:10.1039/c2jm31939j.
   Web of Science ®Google Scholar
• Dou Q, Sha M, Fu H, Wu G. Melting transition of ionic liquid [bmim][PF6] crystal confined in nanopores: a molecular dynamics simulation. J Phys Chem C. 2011;115:18946–18951. doi:10.1021/jp201447g.
   Web of Science ®Google Scholar
• Rettenmeier E, Tokarev A, Blanc C, Dieudonné P, Guari Y, Hesemann P. Imidazolium camphorsulfonamides: chiral catanionic liquid crystals with tunable thermal properties. J Colloid Interface Sci. 2011;356:639–646. doi:10.1016/j.jcis.2011.01.055.
   PubMed Web of Science ®Google Scholar
• Goossens K, Lava K, Nockemann P, Hecke KV, Meervelt LV, Driesen K, Görller-Walrand C, Binnemans K, Cardinaels T. Pyrrolidinium ionic liquid crystals. Chem Eur J. 2009;15:656–674. doi:10.1002/chem.200801566.
   PubMed Web of Science ®Google Scholar
• Xu F, Matsubara S, Matsumoto K, Hagiwara R. Effects of alkyl chain length on properties of N-alkyl-N-methylpyrrolidinium fluorohydrogenate ionic liquid crystals. J Fluorine Chem. 2012;135:344–349. doi:10.1016/j.jfluchem.2012.01.001.
   Web of Science ®Google Scholar
• Sharma R, Mahajan S, Mahajan RK. Physicochemical studies of morpholinium based ionic liquid crystals and their interaction with cyclodextrins. Fluid Phase Equilibr. 2014;361:104–115. doi:10.1016/j.fluid.2013.10.042.
   Web of Science ®Google Scholar
• Ichikawa T, Yoshio M, Hamasaki A, Taguchi S, Liu F, Zeng X, Ungar G, Ohno H, Kato T. Induction of thermotropic bicontinuous cubic phases in liquid-crystalline ammonium and phosphonium salts. J Am Chem Soc. 2012;134:2634–2643. doi:10.1021/ja209010m.
   PubMed Web of Science ®Google Scholar
• Zhou M, Zhang J, Wang S, Boyer D, Guo H, Li W, Wu L. Laterally substituted ionic liquid crystals and the resulting rheological behavior. Soft Matter. 2012;8:7945–7951. doi:10.1039/c2sm25921d.
   Web of Science ®Google Scholar
• Pott T, Meleárd P. New insight into the nanostructure of ionic liquids: a small angle X-ray scattering (SAXS) study on liquid tri-alkyl-methyl-ammonium bis(trifluoromethanesulfonyl)amides and their mixtures. Phys Chem Chem Phys. 2009;11:5469–5475. doi:10.1039/b901582e.
   PubMed Web of Science ®Google Scholar
• Pal SK, Kuma S. Microwave-assisted synthesis of novel imidazolium-based ionic liquid crystalline dimers. Tetrahedron Lett. 2006;47:8993–8997. doi:10.1016/j.tetlet.2006.09.167.
   Web of Science ®Google Scholar
• Getsis A, Mudring AV. Imidazolium based ionic liquid crystals: structure, photophysical and thermal behaviour of [Cnmim]Br•xH2O (n = 12, 14; x=0, 1). Cryst Res Technol. 2008;43:1187–1196. doi:10.1002/crat.200800345.
   Web of Science ®Google Scholar
• Xu F, Matsumoto K, Hagiwara R. Phase behavior of 1-dodecyl-3-methylimidazolium fluorohydrogenate salts (C12MIm(FH)nF, n = 1.0–2.3) and their anisotropic ionic conductivity as ionic liquid crystal electrolytes. J Phys Chem B. 2012;116:10106–10112. doi:10.1021/jp305228u.
   PubMed Web of Science ®Google Scholar
• Xu F, Matsumoto K, Hagiwara R. Effects of alkyl chain length on properties of 1-alkyl-3-methylimidazolium fluorohydrogenate ionic liquid crystals. Chem Eur J. 2010;16:12970–12976. doi:10.1002/chem.201001364.
   PubMed Web of Science ®Google Scholar
• Cardinaels T, Lava K, Goossens K, Eliseeva SV, Binnemans K. 1,10-phenanthrolinium ionic liquid crystals. Langmuir. 2011;27:2036–2043. doi:10.1021/la1047276.
   PubMed Web of Science ®Google Scholar
• Tseng JCW, Rondla R, Su PYS, Lin IJB. The roles of betaine-ester analogues of 1-N-alkyl-3-N′-methyl imidazolium salts: as amphotropic ionic liquid crystals and organogelators. RSC Adv. 2013;3:25151–25158. doi:10.1039/c3ra43067g.
   Web of Science ®Google Scholar
• Schenkel MR, Shao R, Robertson LA, Wiesenauer BR, Clark NA, Gin DL. New ionic organic compounds containing a linear tris(imidazolium) core and their thermotropic liquid crystal behaviour. Liq Cryst. 2013;40:1067–1081. doi:10.1080/02678292.2013.798692.
   Web of Science ®Google Scholar
• Yoshio M, Miyashita Y, Nishio Y. Enthalpy relaxation behavior of liquid-crystalline glasses of an esterified cholesterol derivative and its complex salts with aliphatic amines. Mol Cryst Liq Cryst. 2001;357:27–42. doi:10.1080/10587250108028242.
   Web of Science ®Google Scholar
• Goossens K, Nockemann P, Driesen K, Goderis B, Görller-Walrand C, Hecke KV, Meervelt LV, Pouzet E, Binnemans K, Cardinaels T. Imidazolium ionic liquid crystals with pendant mesogenic groups. Chem Mater. 2008;20:157–168. doi:10.1021/cm702321c.
   Web of Science ®Google Scholar
• Yousif YZ, Othman AA, Al-masoudi WA, Alapati PR. Some novel cholesteric liquid crystals. Liq Cryst. 1992;12:363–368. doi:10.1080/02678299208031053.
   Web of Science ®Google Scholar
• Topala C, Meltzer V. Liquid crystals. 7. The mesogeneous behaviour in the series of some steryl-carboxylates. Revista De Chimie. 2003;54:493–496.
   Web of Science ®Google Scholar
• Lin IJB, Vasam CS. Metal-containing ionic liquids and ionic liquid crystals based on imidazolium moiety. J Organomet Chem. 2005;690:3498–3512. doi:10.1016/j.jorganchem.2005.03.007.
   Web of Science ®Google Scholar
• Seoud OAE, Pires PAR, Abdel-Moghny T, Bastos EL. Synthesis and micellar properties of surface-active ionic liquids: 1-alkyl-3-methylimidazolium chlorides. J Colloid Interface Sci. 2007;313:296–304. doi:10.1016/j.jcis.2007.04.028.
   PubMed Web of Science ®Google Scholar
• Fung YS, Chau SM. Investigation of lithium chloride/ambient-temperature 1-methyl-3-ethylimidazolium chloride-aluminum chloride ionic liquids. 1. Ion interactions in a neutral tetrachloroaluminate melt. Inorg Chem. 1995;34:2371–2376. doi:10.1021/ic00113a018.
   Web of Science ®Google Scholar
• Mahjoor P, Latturner SE. Synthesis and structural characterization of [bpyr]4[V4O4Cl12] and [bpyr]4[Bi4Cl16] grown in ionic liquid [bpyr][AlCl4] (bpyr = 1-butylpyridinium). Cryst Growth Des. 2009;9:1385–1389. doi:10.1021/cg800625w.
   Web of Science ®Google Scholar
• Ko NH, Lee JS, Huh ES, Lee H, Jung KD, Kim HS, Cheong M. Extractive desulfurization using Fe-containing ionic liquids. Energy Fuels. 2008;22:1687–1690. doi:10.1021/ef7007369.
   Web of Science ®Google Scholar
• Zhao D, Fei Z, Scopelliti R, Dyson PJ. Synthesis and characterization of ionic liquids incorporating the nitrile functionality. Inorg Chem. 2004;43:2197–2205. doi:10.1021/ic034801p.
   PubMed Web of Science ®Google Scholar
• Muhammad N, Man Z, Ziyada AK, Bustam MA, Mutalib MIA, Wilfred CD, Rafiq S, Tan IM. Thermophysical properties of dual functionalized imidazolium-based ionic liquids. J Chem Eng Data. 2012;57:737–743. doi:10.1021/je200710t.
   Web of Science ®Google Scholar
• Wei Z, Wei X, Wang X, Wang Z, Liu J. Ionic liquid crystals of quaternary ammonium salts with a 2-hydroxypropoxy insertion group. J Mater Chem. 2011;21:6875–6882. doi:10.1039/c1jm10236b.
   Web of Science ®Google Scholar
• Westphal E, Silva DH, Molin F, Gallardo H. Pyridinium and imidazolium 1,3,4-oxadiazole ionic liquid crystals: a thermal and photophysical systematic investigation. RSC Adv. 2013;3:6442–6454. doi:10.1039/c3ra23456h.
   Web of Science ®Google Scholar
• Luo SC, Sun S, Deorukhkar AR, Lu JT, Bhattacharyya A, Lin IJB. Ionic liquids and ionic liquid crystals of vinyl functionalized imidazolium salts. J Mater Chem. 2011;21:1866–1873. doi:10.1039/c0jm02875d.
   Web of Science ®Google Scholar
• De Roche J, Gordon CM, Imrie CT, Ingram MD, Kennedy AR, Lo Celso F, Triolo A. Application of complementary experimental techniques to characterization of the phase behavior of [C16MIm][PF6] and [C14MIm][PF6]. Chem Mater. 2003;15:3089–3097. doi:10.1021/cm021378u.
   Web of Science ®Google Scholar
• Donaldson T, Staesche H, Lu ZB, Henderson PA, Achard MF, Imrie CT. Symmetric and non-symmetric chiral liquid crystal dimers. Liq Cryst. 2010;37:1097–1110. doi:10.1080/02678292.2010.494412.
   Web of Science ®Google Scholar
• Lee HC, Lu Z, Henderson PA, Achard MF, Mahmood WAK, Yeap GY, Imrie CT. Cholesteryl-based liquid crystal dimers containing a sulfur-sulfur link in the flexible spacer. Liq Cryst. 2012;39:259–268. doi:10.1080/02678292.2011.641753.
   Web of Science ®Google Scholar
• Meng FB, Cui Y, Chen HB, Zhang BY, Jia C. Phase behaviors of comb-like liquid crystalline polysiloxanes containing fluorinated mesogenic units. Polymer. 2009;50:1187–1196. doi:10.1016/j.polymer.2009.01.005.
   Web of Science ®Google Scholar
• Felder-Flesch D, Rupnicki L, Bourgogne C, Donnio B, Guillon D. Liquid-crystalline cholesterol-based [60]fullerene hexaadducts. J Mater Chem. 2006;16:304–309. doi:10.1039/b509081d.
   Web of Science ®Google Scholar
• Yoshizawa H, Mihara T, Koide N. Thermal properties and ionic conductivity of imidazolium salt derivatives having a calamitic mesogen. Mol Cryst Liq Cryst. 2004;423:61–72. doi:10.1080/15421400490502481.
   Web of Science ®Google Scholar