Synthesis and Mesomorphic Properties of Rigid-Core Ionic Liquid Crystals

Kouwer, Paul H. J.; Swager, Timothy M.

doi:10.1021/ja075651a

Cited by 185 publications

(166 citation statements)

References 38 publications

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“…[15a, 42, 46] Because of the strong intermolecular electrostatic interactions, smectic and in some cases also columnar phases are stabilized and nematic mesophases are removed for such systems. [9,28,47] 4) Rodlike or slightly bent molecules in which the imidazolium group is an integral part of the rigid core unit either in the center [48][49][50] or at the periphery [51] represent the fourth and least investigated class of imidazole-based ILCs. Whereas for noncharged 3-substituted 1H-imidazole amphiphiles the number of alkyl chains attached to the imidazole-terminated rodlike core was modified and in this way columnar and micellar cubic mesophases based on hydrogen-bonded aggregates were obtained, [52,53] to our knowledge no such investigation has been carried out for charged imidazolium-based rodlike mesogens.…”

Section: Introductionmentioning

confidence: 99%

Self‐Assembly of Imidazolium‐Based Rodlike Ionic Liquid Crystals: Transition from Lamellar to Micellar Organization

Cheng

Xue-qing

Jing

et al. 2010

Chemistry A European J

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By using aryl-amination chemistry, a series of rodlike 1-phenyl-1H-imidazole-based liquid crystals (LCs) and related imidazolium-based ionic liquid crystals (ILCs) has been prepared. The number and length of the C-terminal chains (at the noncharged end of the rodlike core) and the length of the N-terminal chain (on the imidazolium unit in the ILCs) were modified and the influence of these structural parameters on the mode of self-assembly in LC phases was investigated by polarizing microscopy, differential scanning calorimetry, and X-ray diffraction. For the single-chain imidazole derivatives nematic phases (N) and bilayer SmA2 phases were found, but upon increasing the number of alkyl chains the LC phases were lost. For the related imidazolium salts LC phases were preserved upon increasing the number and length of the C-terminal chains and in this series it leads to the phase sequence SmA-columnar (Col)-micellar cubic (CubI /Pm3n). Elongation of the N-terminal chain gives the reversed sequence. Short N-terminal chains prefer an end-to-end packing of the mesogens in which these chains are separated from the C-terminal chains. Elongation of the N-terminal chain leads to a mixing of N- and C-terminal chains, which is accompanied by complete intercalation of the aromatic cores. In the smectic phases this gives rise to a transition from bilayer (SmA2) to monolayer smectic (SmA) phases. For the columnar and cubic phases the segregated end-to-end packing leads to core-shell aggregates. In this case, elongation of the N-terminal chains distorts core-shell formation and removes CubI and Col phases in favor of single-layer SmA phases. Hence, by tailoring the length of the N-terminal chain, a crossover from taper-shaped to polycatenar LC tectons was achieved, which provides a powerful tool for control of self-assembly in ILCs.

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Section: Introductionmentioning

confidence: 99%

Self‐Assembly of Imidazolium‐Based Rodlike Ionic Liquid Crystals: Transition from Lamellar to Micellar Organization

Cheng

Xue-qing

Jing

et al. 2010

Chemistry A European J

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“…First, we synthesized the monomer with Br" counter-anion, and then the other monomers with different counter-anions were obtained by an anion-exchange process. [50]. Figure 3 shows the 1 H NMR spectra of the monomers with different counter-anions.…”

Section: Results and Discussion 31 Synthesis Of Monomersmentioning

confidence: 99%

Combined main-chain/side-chain ionic liquid crystalline polymer based on ‘jacketing’ effect: Design, synthesis, supra-molecular self-assembly and photophysical properties

Weng¹,

Xie²,

Arges³

et al. 2015

Express Polym. Lett.

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Ionic liquid crystalline polymers (ILCPs) are a class of macromolecular architectures with mesogenic groups and ionic species and they have attracted great interest in the fields of polymer chemistry and materials science lately [1][2][3]. The combination of electrostatic interaction with liquid crystalline (LC) ordering yields ILCPs with excellent mechanical properties, rheological processability, piezoelectric performance, and optical variable performance [1][2][3][4][5][6][7]. Generally, ionic interaction promotes the ILCPs to form ionic clusters resulting in a reversible physical gelation [1,8,9]. Moreover, incorporation of the ions and selection of the type of ion chemistry can effectively improve the miscibility with other polymers. Therefore, ILCPs are versatile candidates to construct new high-performance functional mate- 536Combined main-chain/side-chain ionic liquid crystalline polymer based on 'jacketing' effect: Design, synthesis, supra-molecular self-assembly and photophysical properties Abstract. Reasonably fabricating ordered structures of ionic polymers is very important for the development of novel functional materials. By combining the ions and liquid cry stalline polymer, we successfully designed and synthesized a series of novel combined main-chain/side-chain ionic liquid crystalline polymer (MCSC-ILCPs) containing imidazolium groups and different counter-anions, poly (2,5-bis{[6-(4-butoxy-4!-imidazolium biphenyl)hexyl]oxycarbonyl}styrene salts) poly(BImBHCS-X) with the following types of counter-anions (Br", BF 4 ", PF 6 " and TFSI"). Combined technologies confirmed the chemical structures of the monomers and polymers with imidazolium cation and different counter-anions. Differential scanning calorimetry (DSC), polarized light microscopy (PLM) and one-and two-dimensional wide-angle X-ray diffraction (1D and 2D WAXD) results illustrated that the LC structures and the transitions of ordered structures depended on the nature of the counter-anion employed. The polymers with Br" and BF 4 " counter-anions exhibited smectic A (SmA) LC behavior below the isotropic temperature. The another one, poly(BImBHCS-TFSI) with the large volume of the TFSI" anion destroyed the packing of the LC ordered structure resulting in an amorphous structure. The photophysical properties of the polymers prepared can be adjusted by tuning the ionic interaction of the polymers by switching the counter-anion.

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“…Aus dem Bereich der Flüssigkristallforschung erschien kürzlich eine Publikation, die über den vorteilhaften Effekt von Phenyl-und Biphenylgruppen auf die mesomorphen Eigenschaften ionischer Flüssigkristalle berichtete. [5] Die gegenwärtig wichtigste Klasse der ILs sind Imidazoliumsalze, die generell sp 3 [6] Wir untersuchen Imidazolium-basierte Verbindungen als Vorstufen zur Synthese von NHC-Metallkomplexen; [7] NHCs (N-heterocyclische Carbene) sind eine sehr interessante Klasse von Liganden in der homogenen Katalyse. [8] Sie sind in der Regel stabiler als die Phosphinliganden und wurden bisher als s-Donorliganden mit vernachlässigbarem p-Anteil beschrieben.…”

Section: Sebastian Ahrens Anke Peritz Und Thomas Strassner*unclassified

Maßgeschneiderte Aryl‐Alkyl‐substituierte ionische Flüssigkeiten (TAAILs) – die nächste Generation ionischer Flüssigkeiten

2009

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Synthesis and Mesomorphic Properties of Rigid-Core Ionic Liquid Crystals

Cited by 185 publications

References 38 publications

Self‐Assembly of Imidazolium‐Based Rodlike Ionic Liquid Crystals: Transition from Lamellar to Micellar Organization

Self‐Assembly of Imidazolium‐Based Rodlike Ionic Liquid Crystals: Transition from Lamellar to Micellar Organization

Combined main-chain/side-chain ionic liquid crystalline polymer based on ‘jacketing’ effect: Design, synthesis, supra-molecular self-assembly and photophysical properties

Maßgeschneiderte Aryl‐Alkyl‐substituierte ionische Flüssigkeiten (TAAILs) – die nächste Generation ionischer Flüssigkeiten

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