Mesophase stabilization in ionic liquid crystals through pairing equally shaped mesogenic cations and anions
Abstract
The synthesis and properties of a set of novel ionic liquid crystals with congruently shaped cations and anions are reported to check whether pairing mesogenic cations with mesogenic anions leads to a stabilization of a liquid crystalline phase. To that avail 1-alkyl-3-methyl-triazolium cations with an alkyl chain length of 10, 12, and 14 carbon atoms have been combined with p-alkyloxy-benzenesulfonate anions with different alkyl chain lengths (n = 10, 12, and 14). The corresponding triazolium iodides have been synthesized as reference compounds where the cation and anion have strong size and shape mismatch. The mesomorphic behavior of all compounds is studied by differential scanning calorimetry and polarizing optical microscopy. All compounds except 1-methyl-3-decyltriazolium iodide, which qualifies as an ionic liquid, are thermotropic ionic liquid crystals. All other compounds adopt smectic A phases. As a result, a comparison of the thermal phase behavior of the 1-methyl-3-decyltriazolium bromides to the corresponding p-alkoxy-benzensulfonates reveals that definitely the mesophase is stabilized by pairing the rod-shaped 1-alkyl-3-methyltriazolium cation with a rod-like anion of similar size.
- Authors:
-
- Ruhr-Univ. Bochum, Bochum (Germany)
- Ruhr-Univ. Bochum, Bochum (Germany); Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States)
- Ruhr-Univ. Bochum, Bochum (Germany); Univ. Duisburg Essen, Essen (Germany)
- Publication Date:
- Research Org.:
- Ames Lab., Ames, IA (United States)
- Sponsoring Org.:
- USDOE Advanced Research Projects Agency - Energy (ARPA-E)
- OSTI Identifier:
- 1239155
- Report Number(s):
- IS-J-8856
Journal ID: ISSN 1528-7483
- Grant/Contract Number:
- AC02-07CH11358
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Crystal Growth and Design
- Additional Journal Information:
- Journal Volume: 15; Journal Issue: 11; Journal ID: ISSN 1528-7483
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; ionic liquids; liquid crystals; ionic liquid crystals
Citation Formats
Stappert, Kathrin, Lipinski, Gregor, Kopiec, Gabriel, Spielberg, Eike T., and Mudring, Anja -Verena. Mesophase stabilization in ionic liquid crystals through pairing equally shaped mesogenic cations and anions. United States: N. p., 2015.
Web. doi:10.1021/acs.cgd.5b01023.
Stappert, Kathrin, Lipinski, Gregor, Kopiec, Gabriel, Spielberg, Eike T., & Mudring, Anja -Verena. Mesophase stabilization in ionic liquid crystals through pairing equally shaped mesogenic cations and anions. United States. https://doi.org/10.1021/acs.cgd.5b01023
Stappert, Kathrin, Lipinski, Gregor, Kopiec, Gabriel, Spielberg, Eike T., and Mudring, Anja -Verena. Thu .
"Mesophase stabilization in ionic liquid crystals through pairing equally shaped mesogenic cations and anions". United States. https://doi.org/10.1021/acs.cgd.5b01023. https://www.osti.gov/servlets/purl/1239155.
@article{osti_1239155,
title = {Mesophase stabilization in ionic liquid crystals through pairing equally shaped mesogenic cations and anions},
author = {Stappert, Kathrin and Lipinski, Gregor and Kopiec, Gabriel and Spielberg, Eike T. and Mudring, Anja -Verena},
abstractNote = {The synthesis and properties of a set of novel ionic liquid crystals with congruently shaped cations and anions are reported to check whether pairing mesogenic cations with mesogenic anions leads to a stabilization of a liquid crystalline phase. To that avail 1-alkyl-3-methyl-triazolium cations with an alkyl chain length of 10, 12, and 14 carbon atoms have been combined with p-alkyloxy-benzenesulfonate anions with different alkyl chain lengths (n = 10, 12, and 14). The corresponding triazolium iodides have been synthesized as reference compounds where the cation and anion have strong size and shape mismatch. The mesomorphic behavior of all compounds is studied by differential scanning calorimetry and polarizing optical microscopy. All compounds except 1-methyl-3-decyltriazolium iodide, which qualifies as an ionic liquid, are thermotropic ionic liquid crystals. All other compounds adopt smectic A phases. As a result, a comparison of the thermal phase behavior of the 1-methyl-3-decyltriazolium bromides to the corresponding p-alkoxy-benzensulfonates reveals that definitely the mesophase is stabilized by pairing the rod-shaped 1-alkyl-3-methyltriazolium cation with a rod-like anion of similar size.},
doi = {10.1021/acs.cgd.5b01023},
journal = {Crystal Growth and Design},
number = 11,
volume = 15,
place = {United States},
year = {Thu Jul 23 00:00:00 EDT 2015},
month = {Thu Jul 23 00:00:00 EDT 2015}
}
Web of Science
Works referenced in this record:
First example of interdigitated U-shape benzimidazolium ionic liquid crystals
journal, January 1997
- Lee, Kwang Ming; Lee, Ching Kuan; Lin, Ivan J. B.
- Chemical Communications, Issue 9
Small-Angle X-ray Scattering Studies of Liquid Crystalline 1-Alkyl-3-methylimidazolium Salts
journal, February 2002
- Bradley, A. E.; Hardacre, C.; Holbrey, J. D.
- Chemistry of Materials, Vol. 14, Issue 2
Dicationic imidazolium-based ionic liquids and ionic liquid crystals with variously positioned fluoro substituents
journal, January 2009
- Li, Xiaoju; Bruce, Duncan W.; Shreeve, Jean'ne M.
- Journal of Materials Chemistry, Vol. 19, Issue 43
Polyfluoroalkyl, Polyethylene Glycol, 1,4-Bismethylenebenzene, or 1,4-Bismethylene-2,3,5,6-Tetrafluorobenzene Bridged Functionalized Dicationic Ionic Liquids: Synthesis and Properties as High Temperature Lubricants
journal, April 2008
- Zeng, Zhuo; Phillips, Benjamin S.; Xiao, Ji-Chang
- Chemistry of Materials, Vol. 20, Issue 8
Bis-cationic ionic liquid crystals
journal, January 2014
- Yang, Mei; Stappert, Kathrin; Mudring, Anja-Verena
- J. Mater. Chem. C, Vol. 2, Issue 3
Structural Studies of Crystalline 1-Alkyl-3-Methylimidazolium Chloride Salts
journal, January 2004
- Downard, A.; Earle, M. J.; Hardacre, C.
- Chemistry of Materials, Vol. 16, Issue 1
The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals
journal, January 1999
- Holbrey, John D.; Seddon, Kenneth R.
- Journal of the Chemical Society, Dalton Transactions, Issue 13
Imidazolium based ionic liquid crystals: structure, photophysical and thermal behaviour of [C n mim]Br·xH 2 O (n = 12, 14; x=0, 1)
journal, November 2008
- Getsis, A.; Mudring, A. -V.
- Crystal Research and Technology, Vol. 43, Issue 11
Structural and Thermal Behaviour of the Pyrrolidinium Based Ionic Liquid Crystals [C 10 mpyr]Br and [C 12 mpyr]Br
journal, November 2009
- Getsis, Anna; Mudring, Anja-Verena
- Zeitschrift für anorganische und allgemeine Chemie, Vol. 635, Issue 13-14
Pyrrolidinium Ionic Liquid Crystals
journal, January 2009
- Goossens, Karel; Lava, Kathleen; Nockemann, Peter
- Chemistry - A European Journal, Vol. 15, Issue 3
Piperidinium, Piperazinium and Morpholinium Ionic Liquid Crystals
journal, July 2009
- Lava, Kathleen; Binnemans, Koen; Cardinaels, Thomas
- The Journal of Physical Chemistry B, Vol. 113, Issue 28
New triazolium based ionic liquid crystals
journal, January 2014
- Stappert, Kathrin; Ünal, Derya; Mallick, Bert
- Journal of Materials Chemistry C, Vol. 2, Issue 37
Solid-State Structures of Double-Long-Chain Imidazolium Ionic Liquids: Influence of Anion Shape on Cation Geometry and Crystal Packing
journal, May 2011
- Wang, Xinjiao; Vogel, Carola S.; Heinemann, Frank W.
- Crystal Growth & Design, Vol. 11, Issue 5
New ionic liquid crystals based on imidazolium salts
journal, January 2006
- Dobbs, William; Douce, Laurent; Allouche, Lionel
- New Journal of Chemistry, Vol. 30, Issue 4
A new class of double alkyl-substituted, liquid crystalline imidazolium ionic liquids—a unique combination of structural features, viscosity effects, and thermal properties
journal, January 2009
- Wang, Xinjiao; Heinemann, Frank W.; Yang, Mei
- Chemical Communications, Issue 47
Phase Behavior of Lyotropic Liquid Crystals in Linear Alkylbenzene Sulphonate (LAS) Systems in the Presence of Dilute and Concentrated Electrolyte
journal, December 2011
- Stewart, J. A.; Saiani, A.; Bayly, A.
- Journal of Dispersion Science and Technology, Vol. 32, Issue 12
New catanionic surfactants based on 1-alkyl-3-methylimidazolium alkylsulfonates, [CnH2n+1mim][CmH2m+1SO3]: mesomorphism and aggregation
journal, January 2009
- Blesic, Marijana; Swadźba-Kwaśny, Małgorzata; Holbrey, John D.
- Physical Chemistry Chemical Physics, Vol. 11, Issue 21
Smectic Liquid Crystals from Supramolecular Guanidinium Alkylbenzenesulfonates
journal, May 2002
- Mathevet, Fabrice; Masson, Patrick; Nicoud, Jean-François
- Chemistry - A European Journal, Vol. 8, Issue 10
Controllable Columnar Organization of Positively Charged Polycyclic Aromatic Hydrocarbons by Choice of Counterions
journal, June 2009
- Wu, Dongqing; Pisula, Wojciech; Enkelmann, Volker
- Journal of the American Chemical Society, Vol. 131, Issue 28
Designer Ionic Liquid Crystals Based on Congruently Shaped Guanidinium Sulfonates
journal, February 2012
- Butschies, Martin; Frey, Wolfgang; Laschat, Sabine
- Chemistry - A European Journal, Vol. 18, Issue 10
A Novel Modular Approach to Triazole-Functionalized Phthalocyanines Using Click Chemistry
journal, January 2009
- Juríček, Michal; Kouwer, Paul H. J.; Rehák, Juraj
- The Journal of Organic Chemistry, Vol. 74, Issue 1
Influence of the Counteranion on the Ability of 1-Dodecyl-3-methyltriazolium Ionic Liquids to Form Mesophases
journal, January 2015
- Stappert, Kathrin; Ünal, Derya; Spielberg, Eike T.
- Crystal Growth & Design, Vol. 15, Issue 2
Solidification of Ionic Liquids: Theory and Techniques
journal, January 2010
- Mudring, Anja-Verena
- Australian Journal of Chemistry, Vol. 63, Issue 4
Works referencing / citing this record:
1,2,4-Triazolium ions as flexible scaffolds for the construction of polyphilic ionic liquid crystals
journal, January 2018
- Riccobono, Alessio; Parker, Rachel R.; Whitwood, Adrian C.
- Chemical Communications, Vol. 54, Issue 71
Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride
journal, May 2018
- Prodius, Denis; Wilk-Kozubek, Magdalena; Mudring, Anja-Verena
- Acta Crystallographica Section C Structural Chemistry, Vol. 74, Issue 6