Fluorine-containing liquid crystal compound containing ethane bridged bond and -CF2O- bridged bond
A technology of liquid crystal compounds and ethane bridges, which is applied in the direction of liquid crystal materials, chemical instruments and methods, etc., can solve the problems of high melting points of compounds, achieve the effects of reduced melting enthalpy, large dielectric anisotropy, and improved compatibility
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Embodiment 1
[0040] 4′-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(trans-4-n-propylcyclohexyl)ethyl]biphenyl preparation:
[0041] The specific structural formula is as follows:
[0042]
[0043] The preparation process is as follows:
[0044] Step 1: Synthesis of Diethyl (3-fluorobenzyl)phosphonate
[0045]
[0046] Add 498 g of triethyl phosphite and 290 g of m-fluorochlorobenzyl into a 1000 mL three-necked flask, stir and heat under reflux for 7 hours. Then the excess triethyl phosphite was distilled off to obtain 472 g of a colorless transparent liquid with a yield of 95.9%.
[0047] Step 2: Synthesis of 1-fluoro-3-[2-(trans-4-n-propylcyclohexyl)vinyl]benzene
[0048]
[0049]Under the protection of nitrogen, add 185.6g (0.8mol) (3-fluorobenzyl) diethyl phosphonate and 200mL tetrahydrofuran to a 1000mL three-necked flask, add 134.4g (1.2mol) potassium tert-butoxide, after the addition is completed, the Incubate at ~30°C for 1 hour. After the heat preservation...
Embodiment 2
[0070] Using trans-4-pentylcyclohexylcarbaldehyde instead of trans-4-n-propylcyclohexylcarbaldehyde in Example 1, the same method was used to synthesize 4'-[difluoro(3,4,5-trifluorobenzene oxy)methyl]-2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]biphenyl.
[0071] Structure Identification:
[0072] 1 H NMR (δ, CDCl 3 ): 0.85~1.01(m, 7H), 1.15~1.32(m, 10H), 1.51~1.55(m, 4H), 1.75~1.82(m, 2H), 2.65~2.68(m, 2H), 6.96~7.06 (m, 4H), 7.34 (t, 1H), 7.70 (dd, J=7.70Hz, 4H).
[0073] MS (70eV) m / z (%): 401 (100), 234 (38).
[0074] Where m / z=401, the corresponding cracked fragment structure is:
[0075]
[0076] Among them, m / z=234 is the fragment that is further cracked by the fragment of m / z=401, and the corresponding cracked fragment structure is:
[0077]
[0078] The above structural identification data show that the synthesized compound is indeed 4′-[difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-pentyl cyclohexyl) ethyl] biphenyl. The characteristic temp...
Embodiment 3～9
[0080] Respectively use trans-4-methylcyclohexyl formaldehyde, trans-4-ethylcyclohexyl formaldehyde, trans-4-n-butylcyclohexyl formaldehyde, trans-4-n-hexylcyclohexyl formaldehyde, trans-4- N-heptylcyclohexylcarbaldehyde, trans-4-n-octylcyclohexylcarbaldehyde, trans-4-n-nonylcyclohexylcarbaldehyde replace trans-4-n-propylcyclohexylcarbaldehyde in Example 1, the same The method synthesizes:
[0081] 4'-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-methylcyclohexyl)ethyl]biphenyl;
[0082] 4'-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-ethylcyclohexyl)ethyl]biphenyl;
[0083] 4'-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-n-butylcyclohexyl)ethyl]biphenyl;
[0084] 4'-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-n-hexylcyclohexyl)ethyl]biphenyl;
[0085] 4'-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-n-heptylcyclohexyl)ethyl]biphenyl;
[0086] 4'-[Difluoro(3,4,5-trifluorophenoxy)methyl]-2-fluoro-4-[2-(4-n-octy...
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