Nematic Liquid Crystals with a Trifluoromethyl Group

Kelly, Stephen M.; Skelton, G. W.; Jones, John C.; Minter, Vicki; Tuffin, Rachel P.

doi:10.1080/10587250108025060

Cited by 8 publications

(4 citation statements)

References 10 publications

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“…A range of liquid crystalline 1,4-disubstituted [2.2.2]octanes have been designed for use as components of nematic mixtures of positive dielectric anisotropy for TN-LCDs [9][10][11][12][13][14][15][16][17][18][19][20]. A number of these LCs incorporate phenyl rings with a halogen atom in a terminal or lateral position [13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

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Terminal end‐group efficiency for the nematic phase using model bicyclo[2.2.2]octanes

et al. 2007

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The synthesis is reported of new liquid crystals incorporating the 1,4-disubstituted bicyclo[2.2.2]octane ring and a series of substituents in a terminal position on the molecular core. The nature of the terminal substituent is varied from apolar with a small dipole moment to polar with a strong dipole moment. The angle of the dipole moment with respect to the molecular axis is also varied. An updated order of terminal group efficiency for substituents in a terminal position for the nematic phase is provided. The bicyclo[2.2.2]octane ring shields halogen substituents in a lateral position on phenyl rings attached to the bicyclooctane ring to a small degree and reduces the steric efects of these substituents, giving rise to high relative nematic-isotropic transition temperatures.

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Section: Introductionmentioning

confidence: 99%

“…A number of these LCs incorporate phenyl rings with a halogen atom in a terminal or lateral position [13][14][15][16][17][18][19][20]. However, the presence of two or three halogen atoms are required to generate a dipole moment large enough to induce a significant magnitude of the dielectric anisotropy [4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Terminal end‐group efficiency for the nematic phase using model bicyclo[2.2.2]octanes

et al. 2007

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“…A 4,4,4-trifluorobut-2-ene chain attached to a phenolic oxygen has been shown over the years to be a useful fluorinated substituent in medicinal chemistry, agrochemistry, and material sciences . Illustrative examples are shown in Figure .…”

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confidence: 99%

“…The main synthetic strategy used to produce such compounds, 3 , is the reaction between the oxygen-based nucleophile with a suitable electrophilic partner, 2 , using a S N 2 reaction (Figure ). − , While this approach is simple and good yields can be generally obtained, the electrophilic partner bearing a chlorine or a mesylate ( 2 ; R = Cl or OMs) has setbacks (e.g., volatility, stability). Finally, no examples using other nucleophiles have been reported …”

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Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji–Trost Reaction Catalyzed by Palladium Nanoparticles

2015

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A palladium-nanoparticle-catalyzed Tsuji-Trost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl(4,4,4-trifluorobut-2-en-1-yl)carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction. Further synthetic transformations including hydrogenation, the Diels-Alder reaction, and asymmetric dihydroxylation of a product were also examined.

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Complementary Methods for the Introduction of the (E)‐3‐(Pentafluorosulfanyl)allyl Chain unto O‐, N‐, S‐, and C‐Based Nucleophiles

2016

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Two methods for the introduction of the (E)‐3‐(pentafluorosulfanyl)allyl chain unto various nucleophiles were investigated: a palladium‐catalyzed Tsuji–Trost reaction of (E)‐ethyl [3‐(pentafluorosulfanyl)allyl]carbonate and a nucleophilic substitution reaction on (E)‐[3‐(pentafluorosulfanyl)allyl] 4‐methylbenzenesulfonate. Various nucleophiles were examined including phenols, aliphatic and aromatic amines, aliphatic and aromatic thiols and malonates. Overall, the two approaches were found to be complementary as the Tsuji–Trost reaction worked better with phenols while the SN2 reaction generally provided better results with the amines. In addition, the sulfur‐based product could only be obtained using the SN2 reaction while the malonates only worked under the Tsuji–Trost conditions.

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Nematic Liquid Crystals with a Trifluoromethyl Group

Cited by 8 publications

References 10 publications

Terminal end‐group efficiency for the nematic phase using model bicyclo[2.2.2]octanes

Terminal end‐group efficiency for the nematic phase using model bicyclo[2.2.2]octanes

Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji–Trost Reaction Catalyzed by Palladium Nanoparticles

Complementary Methods for the Introduction of the (E)‐3‐(Pentafluorosulfanyl)allyl Chain unto O‐, N‐, S‐, and C‐Based Nucleophiles

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