Synthesis and Mesomorphic Properties of Chiral Esters Comprising Partially Fluorinated Alkoxyalkoxy Terminal Chains and a 1-methylheptyl Chiral Moiety

Żurowska, M.; Dąbrowski, R.; Dziaduszek, Jerzy; Czupryński, K.; Skrzypek, K.; Filipowicz, M.

doi:10.1080/15421400802432428

Cited by 57 publications

(21 citation statements)

References 4 publications

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“…Chiral liquid crystalline substances with three aromatic rings in a molecular core and partially fluorinated alkoxy chain [1][2][3][4][5][6][7][8] are desired materials in liquid crystal display (LCD) technology as they often exhibit a smectic C * A (SmC * A ) phase, showing antiferroelectric properties in the surface-stabilized geometry [9]. Moreover, the tilt angle in these compounds often approaches 45 • , which leads to the optical uniaxiality and, consequently, far better quality of the dark state compared to the SmC * A phase with the smaller tilt angle [10,11].…”

Section: Introductionmentioning

confidence: 99%

“…A phase and kinetics of the isothermal cold crystallization on subsequent heating for (S)-4 -(1-methylheptylcarbonyl)biphenyl-4-yl 4-[7-(2,2,3,3,4,4,4-heptafluorobutoxy)heptyl-1-oxy]benzoate, denoted in short as 3F7HPhH6. This compound belongs to a family of 3FmX 1 PhX 2 r compounds [4][5][6], with a general formula presented in Figure 1a. Differences in the molecular structure within the 3FmX 1 PhX 2 r family exist in the length of the alkoxy chain (m = 0, 2-7) and chiral alkyl chain (r = 4-9), as well as the fluoro substitution of the benzene ring (X 1 , X 2 = {H, F}).…”

Section: Introductionmentioning

confidence: 99%

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Molecular Dynamics and Kinetics of Isothermal Cold Crystallization in the Chiral Smectogenic 3F7FPhH6 Glassformer

Deptuch

Jasiurkowska-Delaporte

Juszyńska-Gałązka

et al. 2021

Crystals

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An investigation of the glass transition of the antiferroelectric smectic CA* phase and cold crystallization of (S)-4′-(1-methylheptylcarbonyl)biphenyl-4-yl 4-[7-(2,2,3,3,4,4,4-heptafluoro- butoxy)heptyl-1-oxy]benzoate (denoted as 3F7HPhH6) by differential scanning calorimetry, polarizing optical microscopy and broadband dielectric spectroscopy is presented. The fragility index mf = 72, classifying 3F7HPhH6 as a glassformer with intermediate fragility, was obtained from the temperature dependence of the α-process relaxation time, measured upon cooling. Duplication of the α-process was observed exclusively upon heating, before the onset of cold crystallization, and is connected with the pre-transitional effect. The presence of two crystal phases likely influences the kinetics of cold crystallization; the idea stems from a comparison with previous results for the 3F7HPhF6 and 3F7HPhH7 compounds. Additionally, the presence of the smectic Cα* sub-phase in a narrow temperature range was proved based on the differential scanning calorimetry and broadband dielectric spectroscopy results, as well as the fractal dimension analysis of the textures obtained by polarizing optical microscopy.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Molecular Dynamics and Kinetics of Isothermal Cold Crystallization in the Chiral Smectogenic 3F7FPhH6 Glassformer

Deptuch

Jasiurkowska-Delaporte

Juszyńska-Gałązka

et al. 2021

Crystals

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“…The compound denoted as C1 has got F atom at X 1 position and the compound denoted as C2 -at X 2 position. Chemical names of the compounds are as follows: [9]. Purity of the compounds was very high, between 99.6-99.9%.…”

Section: Materials Studiedmentioning

confidence: 99%

Investigation of new chiral fluorosubstituted compound exhibiting room temperature antiferroelectric phase

Czerwiec

Żurowska

Garbat

et al. 2011

Opto-Electronics Review

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Influence of the electric field upon alignment of molecules in ferro- and antiferroelectric phases has been studied for two fluoro-substituted compounds exhibiting antiferroelectric phase at room temperature. Two different relaxation processes have been revealed in the ferroelectric as well as antiferroelectric phase. Low temperature value of spontaneous polarization is ca. 130 nC/cm2 for both substances studied. The substances align very well in the external electric field — a mono-domain of the ferroelectric SmC* phase can be obtained in about 3.5 hours.

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“…Compounds 13.n have been prepared as described in the references, 9 the rest of the synthesis of 17.n has been described in the literature. 10 The synthesis of compounds 5, 6.n, 9, 10, 11, 12.n were performed similarly to the reported method. 4 Temperatures and enthalpies of phase transitions for compounds 6.n and 12.n were determined by polarizing thermomicroscopy and DSC technique are described in Table 1.…”

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confidence: 99%

Synthesis of New Chiral Smectic Mesogenes with 4-(2-Phenylethyl)biphenyl and 4-[2-(3-Fluorophenyl)ethyl]biphenyl Molecular Cores

Kula¹,

Spadło²,

Żurowska³

et al. 2010

Synlett

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Two methods of synthesis of chosen 1-[4-(1-methylheptyloxycarbonyl)phenyl]-2-[4¢-(2,2,3,3,4,4,4-heptafluorobutoxyalkoxy)biphenyl-4-yl]ethanes and 1-[3-fluoro-4-(1-methylheptyloxycarbonyl)phenyl]-2-[4¢-(2,2,3,3,4,4,4-heptafluorobutoxyalkoxy)biphenyl-4-yl]ethanes have been proposed, checked and compared. The compounds were prepared by Sonogashira coupling of 4-benzyloxy-4¢-ethynylbiphenyl with appropriate 4-halobenzoate esters followed by parallel hydrogenation of ethynylene bridge and debenzylation of hydroxyl group. The 1-[4-(1-methylheptyloxycarbonyl)phenyl]-2-[4¢-hydroxybiphenyl-4-yl]ethane and 1-[3-fluoro-4-(methoxycarbonyl)phenyl]-2-[4¢-hydroxybiphenyl-4-yl]ethane thus obtained has been transformed into final products by Mitsunobu reaction with w-(2,2,3,3,4,4,4-heptafluorobutoxy)alkan-1-ols, followed by the replacing of an ester terminal chain in the case of second method.

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Synthesis and Mesomorphic Properties of Chiral Esters Comprising Partially Fluorinated Alkoxyalkoxy Terminal Chains and a 1-methylheptyl Chiral Moiety

Cited by 57 publications

References 4 publications

Molecular Dynamics and Kinetics of Isothermal Cold Crystallization in the Chiral Smectogenic 3F7FPhH6 Glassformer

Molecular Dynamics and Kinetics of Isothermal Cold Crystallization in the Chiral Smectogenic 3F7FPhH6 Glassformer

Investigation of new chiral fluorosubstituted compound exhibiting room temperature antiferroelectric phase

Synthesis of New Chiral Smectic Mesogenes with 4-(2-Phenylethyl)biphenyl and 4-[2-(3-Fluorophenyl)ethyl]biphenyl Molecular Cores

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