Design and synthesis of 2(5H)-furanone liquid-crystal compounds based on natural molecules and biphenyl derivatives

Luo, Sukun; Xiong, Jun; Wang, Zhaoyang; Mo, Guang-Zhen

doi:10.1007/s11164-012-0721-8

Cited by 7 publications

(7 citation statements)

References 29 publications

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“…The resultso fX RD measurementso fu nsymmetrical guanidinium ILCs 3(14,n)Cl are summarized in Table 4. In contrast to chlorides 3(14,n)Cl (n = 12, 16,18), in the small-angle X-ray scattering profile of 3 (14,8)Cl as et of reflections was observed that were indexed as (01), (10), (20), (33), and (40) indicating the presence of acolumnar mesophase (Figure 14 a).…”

Section: Synthesis Of the Guanidinium Tyrosinatesmentioning

confidence: 93%

“…[24] More recent examples include metallomesogensw ith aminoa cid ligands, [25] amino-acid-basedf unctionalizedn anoparticles, [26] dendrons, [27] discotic hexakis(phenylethynyl)benzenes, [28] hexacatenar bisamides, [29][30][31] andf uranone liquid crystals. [32,33] On the other hand,t he lyotropic behaviour of peptides was discovered in 1977f or collagen [34] and glycoprotein plant toxins. [35] Lyotropic phases for low molecular weight amino-acid derivatives were first reported in 1980.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Synthesis Of the Guanidinium Tyrosinatesmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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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“…A principle based on characteristics of the binding reaction between biological molecules that affected LC alignment for changing the polarization image was proposed. Such liquid crystal biosensors can be used for detecting cells, proteins, polypeptides, IgGs, and organic phosphorus [13][14][15]. Moreover, the LC sensor has a wide range of advantages such as simple operation, rapid response, high sensitivity, and low cost, which makes it stand out among other sensors.…”

Section: Introductionmentioning

confidence: 99%

Liquid crystal biosensor for detecting ischemia modified albumin

Han

Luo

et al. 2016

Res Chem Intermed

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Ischemia modified albumin detection has great significance in early diagnosis and treatment of myocardial ischemia. In this study, anti-IMA was immobilized on the surface of a glass slide using self-assembled DMOAP and PEI, the binding of antibody and antigen lead to topology-geomorphologic changes on the slide surface, which induced 5CB molecules orientation transformation and modulated light transmittance. Results showed that we can detect concentrations as low as 50 lg/mL IMA. Moreover, this method can be realized with label-free, easy operation without dependence on equipment, and can be observed by the naked eye.

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“…So far, the synthetic schemes of LC materials still have many disadvantages such as low yield, low regioselectivity, inconvenient operations and reactions without considering environment protection. [6][7][8][9][10][11][12][13][14][15] Accordingly, we decided to synthesise the fluoro-containing LC materials via Suzuki cross-coupling reaction. Suzuki cross-coupling reaction is one of the most valuable synthetic method to form biaryls for the Suzuki reaction has many excellent properties such as high stability, broad functional group tolerance and low toxicity.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of fluoro-containing liquid crystal materials via Pd-catalysed room temperature aerobic Suzuki reactions in aqueous media

et al. 2014

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A series of fluoro-containing liquid crystal materials were synthesised at room temperature under aerobic conditions in excellent yields starting from fluoro-containing phenylboronic acids with aryl halides in the presence of a simple hydrophilic trans-PdCl 2 (NH 2 CH 2 COOH) 2 as catalyst via aqueous media Suzuki cross-coupling reactions. Details relevant to the above reactions and to the reaction sequences adopted to get the corresponding fluoro-containing liquid crystal materials are presented. The structures of above catalyst and liquid crystal materials were characterised by element analyses, electrospray mass spectra, 1 H NMR and 13 C NMR.

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Design and synthesis of 2(5H)-furanone liquid-crystal compounds based on natural molecules and biphenyl derivatives

Cited by 7 publications

References 29 publications

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

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

Liquid crystal biosensor for detecting ischemia modified albumin

Efficient synthesis of fluoro-containing liquid crystal materials via Pd-catalysed room temperature aerobic Suzuki reactions in aqueous media

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