488
Views
22
CrossRef citations to date
0
Altmetric
Article

Star-shaped supramolecular ionic liquid crystals based on pyridinium salts

, , , &
Pages 512-522 | Received 16 Apr 2018, Accepted 12 Aug 2018, Published online: 24 Sep 2018

References

  • Wang H, Wang YX, Jin JY, et al. Gold nanoparticle-based colorimetric and “turn-on” fluorescent probe for mercury(II) ions in aqueous solution. Anal Chem. 2008;80:9021–9028.
  • Biedermann F, Schneider HJ. Experimental binding energies in supramolecular complexes. Chem Rev. 2016;116(9):5216–5300.
  • Bai W, Jiang ZW, Ribbe A, et al. Smart organic two-dimensional materials based on a rational combination of non-covalent interactions. Angew Chem Int Ed. 2016;55:10707–10711.
  • Mahadevi AS, Sastry GN. Cooperativity in noncovalent interactions. Chem Rev. 2016;116:2775–2825.
  • Tian Y, Yan XZ, Saha ML, et al. Hierarchical self-assembly of responsive organoplatinum(II) metallacycle−tmv complexes with turn-on fluorescence. J Am Chem Soc. 2016;138:12033–12036.
  • Neel AJ, Hilton MJ, Sigman MS, et al. Exploiting non-covalent π interactions for catalyst design. Nature. 2017;543:637–646.
  • Sawyer N, Watkins AM, Arora PS. Protein domain mimics as modulators of protein−protein interactions. Acc Chem Res. 2017;50:1313–1322.
  • Knight GA, Shaw BD. Long-chain alkylpyridines and their derivatives new examples of liquid crystals. J Chem Soc. 1938;0:682–683.
  • Kawano R, Nazeeruddin MK, Sato A, et al. Amphiphilic ruthenium dye as an ideal sensitizer in conversion of light to electricity using ionic liquid crystal electrolyte. Electrochem Commun. 2007;9:1134–1138.
  • Iannacchione GS. Review of liquid-crystal phase transitions with quenched random disorder. Fluid Phase Equilibria. 2004;177:222–223.
  • Axenov KV, Laschat S. Thermotropic ionic liquid crystals. Materials. 2011;4:206–259.
  • Prasad SK, Sandhya KL, Nair GG, et al. Electrical conductivity and dielectric constant measurements of liquid crystal–gold nanoparticle composites. Liq Cryst. 2006;33:1121–1125.
  • Binnemans K. Ionic liquid crystals. Chem Rev. 2005;105:4148–4204.
  • Kouwer PHJ, Swager TM. Synthesis and mesomorphic properties of rigid-core ionic liquid crystals. J Am Chem Soc. 2007;129:14042–14052.
  • Goossens K, Nockemann P, Driesen K, et al. Imidazolium ionic liquid crystals with pendant mesogenic groups. Chem Mater. 2008;20:157–168.
  • Takahiro S. Dynamic Photoresponsive functions in organized layer systems comprised of azobenzene-containing polymers. Polym J. 2004;36:435–454.
  • Uchida J, Kato T. Liquid-crystalline fork-like dendrons. Liq Cryst. 2017;44:1816–1829.
  • Ovalle S, Westphal E, Gallardo H. Ionic liquid crystals with 1,2,3-triazole + tolane core and a pendant imidazolium unit: mesophases from one- to three-dimensional molecular organisation by the variation of alkoxy chains number and spacer length. Liq Cryst. 2018;45:942–952.
  • Lehmann M. Star mesogens (Hekates)-tailor-made molecules for programming supramolecular functionality. Chem Eur J. 2009;15:3638–3651.
  • Lehmann M. Star-shaped mesogens – hekates: the most basic star structure with three branches. Top Curr Chem. 2011;318:193–223.
  • Lehmann M, Gearba RI, Ivanov DA, et al. New star-shaped mesogens with three different arms on a 1,3,5-benzene core. Mol Cryst Liq Cryst. 2004;411:397–406.
  • Meier H, Lehmann M, Holst HC, et al. Starshaped conjugated compounds forming nematic discotic systems. Tetrahedron. 2004;60:6881–6888.
  • Stackhouse PJ, Wilson A, Lacey D, et al. Synthesis and properties of novel columnar liquid crystals based on symmetrical and non-symmetrical 1,3,5-trisubstituted benzene derivatives. Liq Cryst. 2010;37:1191–1203.
  • Zhang BY, Yao DS, Meng FB, et al. Structure and properties of novel three-armed star-shaped liquid crystals. J Mol Struct. 2005;741:135–140.
  • Goldmann D, Janietz D, Schmidt C, et al. Liquid crystalline 1,3,5-triazines incorporating rodlike azobenzene sub-units. Liq Cryst. 1998;25:711–719.
  • Salisu AA, Kogo AA. New Liquid crystals in the series of 1,3,5-triazine compounds containing azobenzene at the peripheral arms. Bayero J Pure Appl Sci. 2010;3:54–58.
  • Imrie CT, Lu ZB, Pickenb SJ, et al. Oligomeric rod–disc nematic liquid crystals. Chem Commun. 2007;12:1245–1247.
  • Zhao KQ, Bai XY, Xiao B, et al. Star-shaped triphenylene discotic liquid crystalline oligomers and their hydrogen-bonded supramolecular complexes with simple acids. J Mater Chem C. 2015;3:11735–11746.
  • Zelcer A, Donnio B, Bourgogne C, et al. Mesomorphism of hybrid siloxane-triphenylene star-shaped oligomers. Chem Mater. 2007;19:1992–2006.
  • 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;44:1173–1184.
  • Attard GS, Douglass AG, Imrie CT, et al. Liquid-crystalline cyclic trimers derived from benzene-1,3,5-tricarboxylic acid. Liq Cryst. 1992;11:779–784.
  • Campo LD, Moghaddam MJ, Varslot T, et al. Nanocompartmentalization of soft materials with three mutually immiscible solvents: synthesis and self-assembly of three-arm star-polyphiles. Chem Mater. 2015;27:857–866.
  • Lehmann M, Gearba RI, Koch MHJ, et al. Semiflexible star-shaped mesogens as nonconventional columnar liquid crystals. Chem Mater. 2004;16:374–376.
  • 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;43:811–827.
  • Kanibolotsky AL, Perepichka IF, Skabara PJ. Star shaped π-conjugated oligomers and their applications in organic electronics and photonics. Chem Soc Rev. 2010;39:2695–2728.
  • Laschat S, Baro A, Steinke N, et al. Discotic liquid crystals: from tailor-made synthesis to plastic electronics. Angew Chem Int Ed Engl. 2007;46:4832–4887.
  • Ooi YH, Yeap GY, Han CC, et al. Synthesis and smectogenic properties of novel phloroglucinol-based star-shaped liquid crystals containing three peripheral alkyloxylated schiff base arms. Liq Cryst. 2013;40:516–527.
  • Achalkumar AS, Hiremath US, Rao DSS, et al. Selfassembly of hekates-tris(N-salicylideneaniline)s into columnar structures: synthesis and characterization. J Org Chem. 2013;78:527–544.
  • 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;42:2697–2699.
  • Ooi YH, Yeap GY, Han CC, et al. Non-conventional three-armed star-shaped mesogens based on 1,3,5-trisubstituted benzene with azobenzene moieties at the periphery: synthesis, and mesomorphic behavior. Liq Cryst. 2014;41:1017–1033.
  • Pană A, Pasuk I, Micutzc M, et al. Nematic ionic liquid crystals based on pyridinium salts derived from 4-hydroxypyridine. CrystEngComm. 2016;18:5066–5069.
  • Detert H, Lehmann M, Meier H. Star-shaped conjugated systems. Materials. 2010;3:3218–3330.
  • Filippi NG, Mezalira DZ, Ovalle S, et al. Study of the mesomorphic behaviour through the structure modification of azo and acetylene pyridinium and imidazolium-based ionic liquid crystals. Liq Cryst. 2016;43:2163–2190.
  • Pana A, Ilis M, Staicu T, et al. Columnar bis(pyridinium) ionic liquid crystals derived from 4-hydroxypyridine: synthesis, mesomorphism and emission properties. Liq Cryst. 2016;43:381–392.
  • Luo JQ, Zhang L, Lu JM, et al. Polymerised ionic liquid crystals bearing imidazolium and bipyridinium groups. Liq Cryst. 2017;44:1293–1305.
  • Elgueta EY, Parra ML, Diaz EW, et al. Synthesis of novel symmetrical tetra- and hexacatenar di-amides containing 1,3,4-thiadiazole units and a study of their mesomorphic and luminescence properties. Liq Cryst. 2014;41:861–871.
  • 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 Lett. 2008;49:5419–5423.
  • Yang X, Dai H, He Q, et al. Hexagonal columnar mesophases of polycatenar para-phenylene connected bisoxadiazole-based liquid crystals. Liq Cryst. 2013;40:1028–1034.
  • Westphal E, Silva DHD, Molin F, et al. Pyridinium and imidazolium 1,3,4-oxadiazole ionic liquid crystals: a thermal and photophysical systematic investigation. RSC Adv. 2013;3:6442–6454.
  • Patial P, Shaheen A, Ahmad I. Gemini pyridinium surfactants: synthesis and their surface active properties. J Surfact Deterg. 2014;17:929–935.
  • Quagliotto P, Viscardi G, Barolo C, et al. Gemini pyridinium surfactants: synthesis and conductometric study of a novel class of amphiphiles. J Org Chem. 2003;68:7651–7660.
  • Chauhan V, Singh S, Kamboj R, et al. Self-assembly, DNA binding and cytotoxicity trends of ether functionalized gemini pyridinium amphiphiles. J Colloid Interface Sci. 2014;417:385–395.
  • Chauhan V, Singh S, Kaur T, et al. Self-assembly and biophysical properties of gemini 3-alkyloxypyridinium amphiphiles with a hydroxyl-substituted spacer. Langmuir. 2015;31:2956–2966.
  • Liu HF, Zeng FX, Deng L, et al. Brønsted acidic ionic liquids catalyze the high-yield production of diphenolic acid/esters from renewable levulinic acid. Green Chem. 2013;15:81–84.
  • Mahrova M, Pagano F, Pejakovic V, et al. Pyridinium based dicationic ionic liquids as base lubricants or lubricant additives. Tribol Int. 2015;82(A):245–254.
  • Shirai A, Ueta S, Maseda H, et al. Action of reactive oxygen species in the antifungal mechanism of geminipyridinium salts against yeast. Biocontrol Sci. 2012;17:77–82.
  • Yabuhara T, Maeda T, Nagamune H, et al. Synthesis and antimicrobial characteristics of a novel biocide, 4, 4ʹ-(1, 6-dioxyhexamethylene) bis-(1-alkylpyridinium halide). Biocontrol Sci. 2004;9:95–103.
  • Kourai H, Yabuhara T, Shirai A, et al. Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds. Eur J Med Chem. 2006;41:437–444.
  • Noh TH, Kim SA, Lee SY, et al. Submicrosticks versus submicrohelices by sonication-assembly of PdCl2 nanoparticles on those morphologies. Eur J Inorg Chem. 2009;(29–30):4518–4521.
  • Rohini R, Lee CK, Lu JT, et al. Symmetrical 1,3-dialkylimidazolium based ionic liquid crystals. J Chi Chem Soc. 2013;60:745–754.
  • Gupta M, Gupta SP, Rasna MV, et al. A new strategy towards the synthesis of a room-temperature discotic nematic liquid crystal employing triphenylene and pentaalkynylbenzene units. Chem Commun. 2017;53:3014–3017.
  • Roth S, Lehmann M. Mesogenic origami-four-armed, starshaped mesogens as precursors for functional liquid crystal materials. Liq Cryst. 2017;44:1830–1851.
  • Lee SJ, You MK, Lee SW, et al. Star-shaped supramolecular liquid crystals formed by hydrogen bonding between phloroglucinol and stilbazole derivatives with different molecular shapes. Liq Cryst. 2011;38:1289–1299.
  • Stappert K, Unal D, Mallicka B, et al. New triazolium based ionic liquid crystals. J Mater Chem C. 2014;2:7976–7986.
  • Wang XJ, Sternberg M, Kohler FTU, et al. Long-alkyl-chain-derivatized imidazolium salts and ionic liquid crystals with tailor-made properties. RSC Adv. 2014;4:12476–12481.

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.