Designer lyotropic liquid-crystalline systems containing amino acid ionic liquids as self-organisation media of amphiphiles

Ichikawa, Takahiro; Fujimura, Kanae; Yoshio, Masafumi; Kato, Takashi; Ohno, Hiroyuki

doi:10.1039/c3cc45429k

Cited by 38 publications

(35 citation statements)

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“…Asian J. [17,18] We believe that the presentr esult may be an important advance for opening up the development of QL Cm aterials with built-in ILs. [20][21][22][23][24] They have been studied for transporting materials [25][26][27][28][29][30][31] and size-selective separation membranes.…”

Section: Resultsmentioning

confidence: 82%

“…For example, Figure 4f.C omparing these two types of phase diagrams, an otable difference is that aQ II phase is observed for the former type between H II and Lp hases but not for the latter type. [17] Chem. Given that the introduction of asterically bulky group into [AA] weakensi ts hydrogen-bonding ability with solutes, it is plausible to assume that the hydrogen-bond interaction between 1 and [C4mim][AA] having n > 2i sw eaker than that between 1 and [C4mim][AA] having n < 2.…”

Section: Resultsmentioning

confidence: 99%

“…In an effort to clarify how the presence/absence of functional groupsin[ AA] affects the self-organization behavior of 1,we have examined the LC behavior of the mixtures by varying the temperature and component ratio, and then constructed lyotropic LC phase diagrams ( Figures S1-S3 [Ala], [17] As well as the introduction of ah ydroxyl group, that of basic functional groups, such as imidazole and amino groups,o r that of acidic groups, such as ac arboxyl group, is also effective for expanding the LC temperature region of 1. .I ng eneral, the strength of hydrogenbond interaction between solvent and solute is related to the sum of two products, that of the hydrogen-bond donor/acceptor ability of the solvent and the opposite ability of the solute.…”

Section: Resultsmentioning

confidence: 99%

“…As as eries of ILs that are applicable as solventf or self-assembling amphiphiles, we have focusedo na mino acid ILs, [15,16] ac lass of ILs containing amino acids as component ions, because of their superior hydrogen-bond ability that is reminiscent of water.P reviously,w er eported that the use of three imidazolium-based ILs having glycine,a lanine, and leucine as anionsa ss olvent for an eutrala mphiphile leads to the development of lyotropic LC systems. [17] Considering the fact that there are many kinds of amino acids, including natural amino acids and artificially designed ones having diverse functional groups on their side chain, we expected that the extension of our previous study with substituting amino acida nions would lead to the understanding how the presence and/ora bsence of functional groups in the component ion structures of ILs influences their ability as self-assembly mediaofamphiphiles.…”

Section: Introductionmentioning

confidence: 99%

“…[18] We have examined the lyotropic [Leu] hasb een already reported in our previous study. [17] By comparing the lyotropic LC behavior of these mixturesi ncluding the previoust hree ones, we discussh ow the presence and/or absence of functional groups in [C4mim][AA]i nfluences the self-organization behavior of amphiphile 1.…”

Section: Introductionmentioning

confidence: 99%

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A Comprehensive Study on Lyotropic Liquid–Crystalline Behavior of an Amphiphile in 20 Kinds of Amino Acid Ionic Liquids

Fujimura

Ichikawa

Yoshio

et al. 2015

Chemistry An Asian Journal

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We examined the self-organization behavior of a designed amphiphilic molecule in 20 kinds of amino acid ionic liquids composed of 1-butyl-3-methylimidazolium cation and natural amino acid anion ([C4mim][AA]). Addition of [C4mim][AA], regardless of their anion species, to the amphiphile provided homogeneous mixtures showing lyotropic liquid-crystalline (LC) behavior. Upon increasing the component ratio of [C4mim][AA] in the mixtures, a successive change of the mesophase patterns from inverted hexagonal columnar, in some case via bicontinuous cubic, to layered phases was observed. By examining the LC properties at various temperatures and component ratios, we constructed lyotropic LC phase diagrams. Interestingly, the appearance of these phase diagrams is greatly different according to the selection of [AA]. Through comparison, we found that the self-organization behavior of an amphiphile in ionic liquids can be tuned by controlling their ability to form hydrogen-bond, van der Waals, and π-π interactions.

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Section: Resultsmentioning

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Comprehensive Study on Lyotropic Liquid–Crystalline Behavior of an Amphiphile in 20 Kinds of Amino Acid Ionic Liquids

Fujimura

Ichikawa

Yoshio

et al. 2015

Chemistry An Asian Journal

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Tyrosine‐Based Ionic Liquid Crystals: Switching from a Smectic A to a Columnar Mesophase by Exchange of the Spherical Counterion

Neidhardt

Wolfrum

Beardsworth

et al. 2016

Chemistry A European J

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Synthetic strategies were developed to prepare l-tyrosine-based ionic liquid crystals with structural variations at the carboxylic and phenolic OH groups as well as the amino functionality. Salt metathesis additionally led to counterion variation. The liquid-crystalline properties were investigated by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (WAXS, SAXS). The symmetrical ILC chlorides bearing the same alkyl chain at both the ester and ether but either an acyclic or cyclic guanidinium group displayed enantiotropic SmA mesophases with phase widths of 31-88 K irrespective of the head group. It was particularly the replacement of chloride in the acyclic guanidinium ILC by hexafluorophosphate that induced a phase change from SmA to Col . This phase change was attributed to a higher curvature of the interface due to the larger anion, which increased the effective head group cross-sectional area of the amphiphilic ILC. The unsymmetrical acyclic guanidinium chlorides, bearing a constant C ester and variable alkyl chains on the phenolic position, formed enantiotropic SmA phases. The derivative with the largest difference in chain lengths, however, displayed a Col phase, resulting from discoid aggregates of the cone-shaped guanidinium chloride. The results are discussed in terms of the packing parameters, which indicate that the phase behaviour of the thermotropic tyrosine-based ILCs shows analogies to those of lyotropic liquid crystals.

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Current Topics in Ionic Liquid Crystals

et al. 2021

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Ionic liquid crystals (ILCs), that is, ionic liquids exhibiting mesomorphism, liquid crystalline phases, and anisotropic properties, have received intense attention in the past years. Among others, this is due to their special properties arising from the combination of properties stemming from ionic liquids and from liquid crystalline arrangements. Besides interesting fundamental aspects, ILCs have been claimed to have tremendous application potential that again arises from the combination of properties and architectures that are not accessible otherwise, or at least not accessible easily by other strategies. The current review highlights recent developments in ILC research, starting with some key fundamental aspects. Further subjects covered include the synthesis and variations of modern ILCs, including the specific tuning of their mesomorphic behavior. The review concludes with reflections on some applications that may be within reach for ILCs and finally highlights a few key challenges that must be overcome prior and during true commercialization of ILCs.

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Designer lyotropic liquid-crystalline systems containing amino acid ionic liquids as self-organisation media of amphiphiles

Abstract: Amino acid ionic liquids provide suitable media for lyotropic liquid-crystalline systems whose self-organisation behaviour is tuneable by the selection of amino acid anions.

Cited by 38 publications

References 33 publications

A Comprehensive Study on Lyotropic Liquid–Crystalline Behavior of an Amphiphile in 20 Kinds of Amino Acid Ionic Liquids

A Comprehensive Study on Lyotropic Liquid–Crystalline Behavior of an Amphiphile in 20 Kinds of Amino Acid Ionic Liquids

Tyrosine‐Based Ionic Liquid Crystals: Switching from a Smectic A to a Columnar Mesophase by Exchange of the Spherical Counterion

Current Topics in Ionic Liquid Crystals

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