458
Views
5
CrossRef citations to date
0
Altmetric
Article

Imidazole and benzoimidazole derived new ionic liquid crystal compounds: synthesis, characterisation, mesomorphic properties and DFT computations

ORCID Icon, , &
Pages 1140-1150 | Received 24 Jul 2020, Accepted 07 Nov 2020, Published online: 11 Dec 2020

References

  • Binnemans K. Ionic liquid crystals. Chem Rev. 2005;105(11):4148–4204.
  • Axenov KV, Laschat S. Thermotropic ionic liquid crystals. Materials. 2011;4(1):206–259.
  • Laschat S. Progress in liquid chemistry. Beilstein J Org Chem. 2009;5. DOI:10.3762/bjoc.5.48.
  • Laschat S. Progress in liquid chemistry II. Beilstein J Org Chem. 2012;8:118–119.
  • Goossens K, Lava K, Bielawski CW, et al. Ionic liquid crystals: versatilematerials. Chem Rev. 2016;116(8):4643–4807.
  • Zhang Y, Shen Y, Li J, et al. Electrochemical functionalization of single-walled carbon nanotubes in large quantities at a room-temperature ionic liquid supported three-dimensional network electrode. Langmuir. 2005;21:4797–4800.
  • Shen Y, Zhang Y, Zhang Q, et al. Immobilization of ionic liquid with polyelectrolyte as carrier. Chem Commun. 2005;33(33):4193–4195.
  • Weber CF, Puchta R, van Eikema Hommes NJR, et al. Transition-State effects of ionic liquids in substitution reactions of PtII complexes. Angew Chem Int Ed. 2005;44(37):6033–6038.
  • Li J, Shen Y, Zhang Y, et al. Room-temperature ionic liquids as media to enhance the electrochemical stability of self-assembled monolayers of alkanethiols on gold electrodes. Chem Commun. 2005;3:360–362.
  • Zhang J, Bond AM. Conditions required to achieve the apparent equivalence of adhered solid-and solution-phase voltammetry for ferrocene and other redox-active solids in ionic liquids. Anal Chem. 2003;75(11):2694–2702.
  • Chiou JY, Chen JN, Lei JS, et al. Ionic liquid crystals of imidazolium salts with a pendant hydroxyl group. J Mat Chem. 2006;16(29):2972–2977.
  • Lee CK, Huang HW, Lin IJ, et al. Simple amphiphilic liquid crystalline N-alkylimidazolium salts. A new solvent system providing a partially ordered environment. Chem Commun. 2000;19(19):1911–1912.
  • Fan SY, Xu HT, Li QG, et al. Discotic mesogens based on triphenylene-fused benzimidazole or perimidine: facile synthesis, mesomorphism, optical properties and self-assembly. Liq Cryst. 2020;47(7):1041–1054. .
  • Goossens K, Nockemann P, Driesen K, et al. Imidazolium ionic liquid crystals with pendant mesogenic groups. Chem Mater. 2008;20(1):157–168.
  • Biswas M, Dule M, Samanta PN, et al. Imidazolium-based ionic liquids with different fatty acid anions: phase behavior, electronic structure and ionic conductivity investigation. Phys Chem Chem Phys. 2014;16(30):16255–16263.
  • Jhong HR, Wong DSH, Wan CC, et al. A novel deep eutectic solvent-based ionic liquid used as electrolyte for dye-sensitized solar cells. Electrochem Commun. 2009;11(1):209–211.
  • Yazaki S, Funahashi M, Kato T, et al. An electrochromic nanostructured liquid crystal consisting of π-conjugated and ionic moieties. J Am Chem Soc. 2008;130(40):13206–13207.
  • Dobbs W, Suisse JM, Douce L, et al. Electrodeposition of silver particles and gold nanoparticles from ionic liquid‐crystal precursors. Angew Chem Int Ed. 2006;45(25):4179–4182.
  • Noujeim N, Samsam S, Eberlin L, et al. Mesomorphic and ion conducting properties of dialkyl (1, 4-phenylene) diimidazolium salts. Soft Matter. 2012;8(42):10914–10920.
  • Fernandez AA, Kouwer PH. Key developments in ionic liquid crystals. Int J Mol Sci. 2016;17(5):731.
  • Gordon CM, Holbrey JD, Kennedy AR, et al. Ionic liquid crystals: hexafluorophosphate salts. J Mat Chem. 1998;8(12):2627–2636.
  • Bowlas CJ, Bruce DW, Seddon KR, et al. Liquid-crystalline ionic liquids. Chem Commun. 1996;14(14):1625–1626.
  • Bradley AE, Hardacre C, Holbrey JD, et al. Small-angle X-ray scattering studies of liquid crystalline 1-alkyl-3-methylimidazolium salts. Chem Mater. 2002;14(2):629–635.
  • Motoyanagi J, Fukushima T, Aida T, et al. Discotic liquid crystals stabilized by interionic interactions: imidazolium ion-anchored paraffinic triphenylene. Chem Commun. 2005;1(1):101–103.
  • Catanescu O, Grigoras M, Colotin G, et al. Synthesis and characterization of some aliphatic-aromatic poly (Schiff base)s. Eur Polym J. 2001;37(11):2213–2216.
  • Mohammad AT, Srinivasa HT, Mohammed HM, et al. Synthesis mesomorphic and theoretical studies of some new unsymmetrical dimeric ethers of 6-amino-1,3-dimethyluracil and biphenyl cores. J Mol Stru. 2016;1117:201–207.
  • Filippi NG, Mezalira DZ, Ovalle S, et al. Study of the mesomorphicbehaviour through the structure modification of azo and acetylene pyridinium and imidazolium-based ionic liquid crystals. Liq Cryst. 2016;43:2163–2190.
  • Sideris PJ, Chen Y, Gobet M, et al. Alkyl chain length effects of hydroxyl-functionalized imidazolium ionic liquids in the ionothermal synthesis of LiFePO4. Phosphorus Sulf Sil Relat Element. 2019;194(4–6):292–296.
  • Benzon KB, Varghese HT, Panicker CY, et al. Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO, NBO, MEP analysis and molecular docking study of 2-(4-hydroxyphenyl)-4, 5-dimethyl-1H-imidazole 3-oxide. Spectro chimica Acta Part A. 2015;146:307–322.
  • Demircioğlu Z, Özdemir FA, Dayan O, et al. Synthesis, X-ray diffraction method, spectroscopic characterization (FT-IR, 1H and 13C NMR), antimicrobial activity, Hirschfield surface analysis and DFT computations of novel sulfonamide derivatives. J Mol Stru. 2018;1161:122–137.
  • Yeap GY, Mohammad AT, Osman H, et al. Synthesis, spectroscopic and mesomorphic studies on heterocyclic liquid crystals with 1, 3-oxazepine-4, 7-dione, 1, 3-oxazepane-4, 7-dione and 1, 3-oxazepine-1, 5-dione cores. J Mol Stru. 2010;982(1–3):33–44.
  • Mohammad AT, Srinivasa HT, Hariprasad S, et al. Enhanced liquid crystal properties in symmetric ethers containing the oxazepine core: synthesis and characterization of seven member heterocyclic dimers. Tetrahedron. 2016;72(27–28):3948–3957.
  • Yeap GY, Osman F, Imrie CT, et al. Non-symmetric chiral liquid crystal dimers. Preparation and characterisation of the (S)-(benzylidene-4′-substitutedaniline)-2″-methylbutyl-4‴-(4″″-phenyloxy)-benzoateoxy) hexanoates. J Mol Struc. 2016;1111:118–125.
  • Wu BP, Pang ML, Tan TF, et al. The T′ phase and its ‘sandwich-like layer’structure as shown by ionic liquid crystals containing a biphenyl ester-based rigid-core modified by 3-alkylimidazolium salts. Liq Cryst. 2012;39(5):579–594.
  • Nestor ST, Heinrich B, Sykora RA, et al. Methimazolium-based ionic liquid crystals: emergence of mesomorphic properties via a sulfur motif. Tetrahedron. 2017;73(36):5456–5460.
  • Lan X, Bai L, Li X, et al. Cholesteryl-containing ionic liquid crystals composed of alkylimidazolium cations and different anions. J Mol Struc. 2014;1075:515–524.
  • Bréfuel N, Vang I, Shova S, et al. FeII Spin crossover materials based on dissymmetrical N4 Schiff bases including 2-pyridyl and 2R-imidazol-4-yl rings: synthesis, crystal structure and magnetic and mössbauer properties. Polyhedron. 2007;26(8):1745–1757.
  • Starkulla G, Kaller M, Frey W, et al. Liquid crystalline imidazolium salts bearing 5-phenylpyrimidine: dependence of mesomorphic properties on spacer lengths, terminal N-alkyl group and counterions. Liq Cryst. 2011;38:1515–1529.
  • Zhang Q, Shan C, Wang X, et al. New ionic liquid crystals based on azobenzene moiety with two symmetric imidazolium ion group substituents. Liq Cryst. 2008;35(11):1299–1305.
  • Wei B, Tan S, Liang T, et al. Synthesis, structural and electrochemical characterization of benzimidazole compounds exhibiting a smectic C liquid crystal phase. J Mol Struc. 2017;1133:392–397.
  • Manesh AA, Zebarjadian MH. Synthesis of three new branched octadentate (N8) Schiff Base and competitive Lithium-7 NMR study of the stoichiometry and stability constant of Mn2+, Zn2+ and Cd2+ complexes in acetonitrile–[(BMIM)(PF6)] mixture. J Mol Struc. 2020;1199:126965.
  • Imrie CT, Henderson PA. Liquid crystal dimers and higher oligomers: between monomers and polymers. Chem Soc Rev. 2007;36(12):2096–2124.
  • Imrie CT, Henderson PA, Yeap GY. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36(6–7):755–777.
  • Zhao Y, Truhlar DG. A density functional that accounts for medium-range correlation energies in organic chemistry. Org Lett. 2006;8(25):5753–5755.
  • Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theo Chem Acc. 2008;120:215–241.
  • Hay PJ, Wadt WR. Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals. J Chem Phys. 1985;82(1):299–310.
  • Paterson DA, Gao M, Kim YK, et al. Understanding the twist-bendnematic phase: the characterisation of 1-(4-cyanobiphenyl-4 ‘-yloxy)-6-(4-cyanobiphenyl-4ʹ-yl)hexane (CB6OCB) and comparison with CB7CB. Soft Mat. 2016;12(32):6827–6840. .
  • Paterson DA, Abberley JP, Harrison WT, et al. Cyanobiphenyl-based liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2017; 44:127–146.
  • Abberley JP, Jansze SM, Walker R, et al. Structure-property relationships in twist-bend nematogens: the influenceof terminal groups. Liq Cryst. 2017;44:68–83.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.