Non-symmetrical bent-shaped liquid crystals based on a laterally substituted naphthalene central core with four ester groups

Kohout, Michal; Svoboda, Jiřı́; Novotná, Vladimı́ra; Pociecha, Damian

doi:10.1080/02678292.2011.596949

Cited by 26 publications

(15 citation statements)

References 29 publications

(52 reference statements)

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“…Recently, many homologous series have been documented based on naphthalene-core LCs [ 53 , 54 , 55 , 56 , 57 ]. In our previous study [ 45 ], a homologous series of (E)-4-(4-(hexyloxyphenyl diazenylnaphthalene-1-yl-4′-alkoxybenzoate was synthesized and its mesomorphic properties evaluated.…”

Section: Introductionmentioning

confidence: 99%

Synthetic, Mesomorphic, and DFT Investigations of New Nematogenic Polar Naphthyl Benzoate Ester Derivatives

et al. 2021

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Four new non-symmetrical derivatives based on central naphthalene moiety, 4-((4–(alkoxy)phenyl) diazenyl)naphthalen–1–yl 4–substitutedbenzoate (In/x), were prepared, and their properties were investigated experimentally and theoretically. The synthesized materials bear two wing groups: an alkoxy chain of differing proportionate length (n = 6 and 16 carbons) and one terminal attached to a polar group, X. Their molecular structures were elucidated via elemental analyses and FT-IR and NMR spectroscopy. Differential scanning calorimetry (DSC) and polarized optical microscopy (POM) were carried out to evaluate their mesomorphic properties. The results of the experimental investigations revealed that all the synthesized analogues possess only an enantiotropic nematic (N) mesophase with a high thermal stability and broad range. Density functional theory (DFT) calculations were in accordance with the experimental investigations and revealed that all prepared materials are to be linear and planar. Moreover, the rigidity of the molecule increased when an extra fused ring was inserted into the center of the structural shape, so its thermal and geometrical parameters were affected. Energy gap predictions confirmed that the I16/c derivative is more reactive than other compounds.

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Section: Introductionmentioning

confidence: 99%

Synthetic, Mesomorphic, and DFT Investigations of New Nematogenic Polar Naphthyl Benzoate Ester Derivatives

et al. 2021

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“…3 . As it was reported for other bent-shaped materials [ 4 , 47 – 49 ], the type of mesophase depends on the orientation of the ester linkage group as well as on the length and character of the terminal chains.…”

Section: Resultsmentioning

confidence: 52%

“…For the preparation of series of materials IV – VI , we utilized lengthening arms of phenols 7a – c and two-ring acids 8 – 10 . All intermediates were obtained previously by known methods [ 47 – 49 ].…”

Section: Resultsmentioning

confidence: 99%

Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core

Kovářová¹,

Světlík²,

Kozmı́k³

et al. 2014

Beilstein J. Org. Chem.

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SummaryBent-shaped mesogens possessing a biphenyl as a central core have been synthesized and the role of the terminal chain and the orientation of the ester as a linkage group have been investigated. For the studied molecular core we have established that both parameters play an important role for the mesomorphic properties. The polyfluoroalkyl terminal chain supports the formation of mesophases, and the introduction of a chiral lactate terminal chain destabilizes mesophases for the first type of mutual orientation of ester groups, attached to the central core. On the contrary, for the opposite orientation of esters, the terminal chain has no effect on the mesomorphic properties, and columnar phases have been found for all compounds. A unique phase sequence has been found for the mesogen with the fluorinated chain. A generalized tilted smectics, SmCG, have been observed in a temperature interval between two different lamellar SmCP phases and characterized by X-ray and dielectric measurements. The dielectric spectroscopy data are unique and presented for the first time in the SmCG phase providing new information about the molecular dynamics.

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“…Our results show that the previously studied selector adopts a bent conformation. The stability of such conformation should be rather high, since the aromatic unit (8chloro-7-hydroxynaphthalene-2-carboxylic acid) was used previously as a central core of bent-shaped liquid crystals, where it secured the bent molecular shape [35]. The bent molecular shape of the selector is most probably detrimental to effective interaction with analytes, due to the accumulation of most polar interaction sites at one side of the selector, where they could be sterically hindered.…”

Section: Naphthalene Core Substitution Versus Enantiorecognition Propertiesmentioning

confidence: 99%

Design and synthesis of naphthalene‐based chiral strong cation exchangers and their application for chiral separation of basic drugs

Herciková

Spálovská

Frühauf

et al. 2021

J of Separation Science

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In continuation of our efforts to synthesize a highly dedicated strong cation exchanger, we introduce four chiral stationary phases based on a laterally substituted naphthalene core featuring chiral 2-aminocyclohexansulfonic acid as the chiral cation-exchange site. The selectors were modified with two different terminal units, which enabled immobilization to the silica support by thiolene radical reaction or azide-yne click chemistry. The chromatographic parameters of these chiral stationary phases were determined using a set of chiral amines, mainly from the family of β-blocker pharmaceuticals. The chiral stationary phases immobilized by means of click chemistry were found to be superior to those possessing the sulfide linker to the silica support. The chromatographic results and visualization of density functional theory-calculated conformations of the selectors hint at a combination of a steric and electronic effect of the triazole ring in the course of chiral resolution of the target analytes.

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Non-symmetrical bent-shaped liquid crystals based on a laterally substituted naphthalene central core with four ester groups

Cited by 26 publications

References 29 publications

Synthetic, Mesomorphic, and DFT Investigations of New Nematogenic Polar Naphthyl Benzoate Ester Derivatives

Synthetic, Mesomorphic, and DFT Investigations of New Nematogenic Polar Naphthyl Benzoate Ester Derivatives

Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core

Design and synthesis of naphthalene‐based chiral strong cation exchangers and their application for chiral separation of basic drugs

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