424
Views
16
CrossRef citations to date
0
Altmetric
Articles

When size matters: exploring the potential of aminocyclopropenium cations as head groups in triphenylene-derived ionic liquid crystals in comparison with guanidinium and ammonium units

, , , , , & show all
Pages 1250-1258 | Received 01 Dec 2017, Accepted 10 Jan 2018, Published online: 22 Jan 2018

References

  • Goossens K, Lava K, Bielawski CW, et al. Ionic liquid crystals: versatile materials. Chem Rev. 2016;116(8):4643–4807.
  • Axenov KV, Laschat S. Thermotropic ionic liquid crystals. Materials. 2011;4(12):206–259.
  • Mansueto M, Laschat S. Ionic liquid crystals. In: Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. Vol. 6. 2nd ed. Weinheim: Wiley-VCH; 2014. p. 231–280.
  • Douce L, Suisse J-M, Guillon D, et al. Imidazolium-based liquid crystals: a modular platform for versatile new materials with finely tuneable properties and behaviour. Liq Cryst. 2011;38(11–12):1653–1661.
  • Chen S, Eichhorn SH. Ionic discotic liquid crystals. Isr J Chem. 2012;52(10):830–843.
  • Mohammad A, Inamuddin. Green solvents II: properties and applications of ionic liquids. Dordrecht: Springer; 2012. p. 79–118.
  • Pal K. Biosensors nanotechnology. Berkeley (MA): Scrivener Publishing; 2014. p. 267–314.
  • Israelachvili JN, Mitchell DJ, Ninham BW. Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers. J Chem Soc Faraday Trans 2 Mol Chem Phys. 1976;72:1525–1568.
  • Israelachvilli. Intermolecular and surface forc. 3rd ed. London: Academic Press; 2010.
  • Neidhardt MM, Wolfrum M, Beardsworth S, et al. Tyrosine-based ionic liquid crystals: switching from a smectic A to a columnar mesophase by exchange of the spherical counterion. Chem Eur J. 2016;22(46):16494–16504.
  • Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116(3):1139–1241.
  • Sergeyev S, Pisula W, Geerts YH. Discotic liquid crystals: a new generation of organic semiconductors. Chem Soc Rev. 2007;36(12):1902.
  • 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(26):4832–4887.
  • Bushby RJ, Kawata K. Liquid crystals that affected the world: discotic liquid crystals. Liq Cryst. 2011;38(11–12):1415–1426.
  • Kumar S. Playing with discs. Liq Cryst. 2009;36(6–7):607–638.
  • Pal SK, Setia S, Avinash BS, et al. Triphenylene-based discotic liquid crystals: recent advances. Liq Cryst. 2013;40(12):1769–1816.
  • Lee JJ, Yamaguchi A, Alam MA, et al. Discotic ionic liquid crystals of triphenylene as dispersants for orienting single-walled carbon nanotubes. Angew Chem Int Ed. 2012;51(34):8490–8494.
  • Alam MA, Motoyanagi J, Yamamoto Y, et al. “Bicontinuous cubic” liquid crystalline materials from discotic molecules: a special effect of paraffinic side chains with ionic liquid pendants. J Am Chem Soc. 2009;131(49):17722–17723.
  • Motoyanagi J, Fukushima T, Aida T. Discotic liquid crystals stabilized by interionic interactions: imidazolium ion-anchored paraffinic triphenylene. Chem Commun. 2005;1:101.
  • Keller-Griffith R, Ringsdorf H, Vierengel A. Structural variations in amphiphiles: discoidal multivalent cations. Colloid Polym Sci. 1986;264(11):924–935.
  • Kumar S, Gupta SK. The first examples of discotic liquid crystalline gemini surfactants. Tetrahedron Lett. 2010;51(41):5459–5462.
  • Kumar S, Pal SK. Synthesis and characterization of novel imidazolium-based ionic discotic liquid crystals with a triphenylene moiety. Tetrahedron Lett. 2005;46(15):2607–2610.
  • Pal SK, Kumar S. Microwave-assisted synthesis of novel imidazolium-based ionic liquid crystalline dimers. Tetrahedron Lett. 2006;47(50):8993–8997.
  • Pal SK, Kumar S. Novel triphenylene-based ionic discotic liquid crystalline polymers. Liq Cryst. 2008;35(4):381–384.
  • Gupta SK, Kumar S. Novel triphenylene-ammonium-ammonium-triphenylene-based discotic ionic liquid crystalline dimers. Liq Cryst. 2012;39(12):1443–1449.
  • Cui L, Zhu L. Ionic interaction induced novel ordered columnar mesophases in asymmetric discotic triphenylene salts. Liq Cryst. 2006;33(7):811–818.
  • Nayak A, Suresh KA, Kumar Pal S, et al. Films of novel mesogenic molecules at air/water and air/solid interfaces. J Phys Chem B. 2007;111(38):11157–11161.
  • Kumar S, Pal SK. Ionic discotic liquid crystals: synthesis and characterization of pyridinium bromides containing a triphenylene core. Tetrahedron Lett. 2005;46(23):4127–4130.
  • Sauer S, Steinke N, Baro A, et al. Guanidinium chlorides with triphenylene moieties displaying columnar mesophases. Chem Mater. 2008;20(5):1909–1915.
  • Bandar JS, Lambert TH. Aminocyclopropenium ions: synthesis, properties, and applications. Synthesis. 2013;45(18):2485–2498.
  • Wallace AJ, Jayasinghe CD, Polson MIJ, et al. Cyclopropenium cations break the rules of attraction to form closely bound dimers. J Am Chem Soc. 2015;137(49):15528–15532.
  • Walst KJ, Yunis R, Bayley PM, et al. Synthesis and physical properties of tris[dialkylamino]cyclopropenium bistriflamide ionic liquids. RSC Adv. 2015;5(49):39565–39579.
  • Curnow OJ, Holmes MT, Ratten LC, et al. A facile route to functionalised, protic and chiral ionic liquids based on the triaminocyclopropenium cation. RSC Adv. 2012;2(29):10794–10797.
  • Freyer JL, Brucks SD, Gobieski GS, et al. Clickable poly[ionic liquids]: a materials platform for transfection. Angew Chem. 2016;128(40):12570–12574.
  • Mir R, Dudding T. A Au[I]-precatalyst with a cyclopropenium counterion: an unusual ion pair. J Org Chem. 2016;81(6):2675–2679.
  • Bandar JS, Tanaset A, Lambert TH. Phase-transfer and other types of catalysis with cyclopropenium ions. Chem Eur J. 2015;21(20):7365–7368.
  • Mirabdolbaghi R, Dudding T, Stamatatos T. A class of phase-transfer catalyst with interionic strain: insight into the bonding of disubstituted N- vs carbene-stabilized NI-centered cations. Org Lett. 2014;16(11):2790–2793.
  • Mishiro K, Hu F, Paley DW, et al. Macrosteres: the deltic guanidin­ium ion. Eur J Org Chem. 2016;2016(9):1655–1659.
  • Butschies M, Sauer S, Kessler E, et al. Influence of N-alkyl substituents and counterions on the structural and mesomorphic properties of guanidinium salts: experiment and quantum chemical calculations. ChemPhysChem. 2010;11(17):3752–3765.
  • Cooke G, Hell F, Violini S. A convenient route to 2-[hydroxy]-3,6,7,10,11-pentaalkyloxytriphenylenes. Synth Commun. 1997;27(21):3745–3748.
  • Mary A, Renko DZ, Guillou C, et al. Potent acetylcholinesterase inhibitors: design, synthesis, and structure–activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem. 1998;6(10):1835–1850.
  • Kantlehner W, Haug E, Mergen WW, et al. Orthoamide, XL. Herstellung von 1,1,2,3,3-Pentasubstituierten Und 1,1,2,2,3,3-Hexasubstituierten Guanidiniumsalzen Sowie von 1,1,2,3,3-Pentaalkylguanidinen. Liebigs Ann Chem. 1984;1984(1):108–126.
  • Sauer S. Synthese und Charakterisierung neuartiger flüssigkristalliner Guanidiniumsalze [Ph.D. thesis]. Berlin: Universität Stuttgart; 2009.
  • Abel EW, Armitage DA, Willey GR. 11. Reactions of aminosilanes and disilazanes with halogeno-compounds of phosphorus and arsenic. J Chem Soc Resumed. 1965;57–61.
  • Pratt JR, Massey WD, Pinkerton FH, et al. Organosilicon compounds. XX. Synthesis of aromatic diamines via trimethylsilyl-protecting aniline intermediates. J Org Chem. 1975;40(8):1090–1094.
  • Weiss R, Schloter K. Stable radical dications. Tetrahedron Lett. 1975;16(40):3491–3494.
  • Wu MT, Taub D, Patchett AA. Preparation and hydrolysis of phenylbisdialkylaminocyclopropenium cations. Tetrahedron Lett. 1976;17(28):2405–2408.
  • Tobey SW, West R. Pentachlorocyclopropane1. J Am Chem Soc. 1966;88(11):2478–2481.
  • Yoshida Z, Tawara Y. Aminocyclopropenium ion. J Am Chem Soc. 1971;93(10):2573–2574.
  • Johnson RW. Electrochemistry of heterosubstituted cyclopropenyl cations. Tetrahedron Lett. 1976;17(8):589–592.
  • Pal S. Synthesis, Characterisation and Self-assembly of Functionalizrd Soft Nanomaterials [Ph.D. thesis].  Bangalore: Jawaharlal Nehru University, Raman Research Institute; 2008.

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.