N-methyl substituted benzimidazole side fluorine liquid crystal compound with large birefringence and preparation method thereof
A liquid crystal compound, methyl substitution technology, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve the problems of not enough types, limited applications, and Δn is not large enough, etc., to improve the corresponding speed, simple steps, wide Effects of Nematic Intervals
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Embodiment 1
[0034] 1. Preparation of 4-(4-(1,3-dioxolan-2-yl)-2-fluorophenyl)-2-methylbut-3-yn-2-ol
[0035] Add 10g (50.0mmol) of 2-fluoro-p-bromobenzaldehyde, 2.2g (12.6mmol) of p-toluenesulfonic acid, and 70g (1120mmol) of ethylene glycol into a 250mL single-necked bottle equipped with a condenser tube and a stirring bar, and add 100mL of dry chloroform was refluxed at 60°C for 6h. After the reaction, the solvent was evaporated under reduced pressure, and 2.1g (23.8mmol) of 2-methyl-3-butyn-2-ol, 2-iodide Copper 0.2g (1mmol), triphenylphosphine 0.6g (2.2mmol), and 80mL triethylamine was added as the reaction solvent, nitrogen protection was introduced, and after reflux reaction at 80°C for 1 hour, tetrakistriphenylphosphine palladium was added 0.5g (0.44mmol), continue to react for 8 hours. After the reaction, the reaction system was diluted with water, extracted with dichloromethane, the organic phase was separated, and the aqueous phase was repeatedly extracted with dichloromethane,...
Embodiment 2
[0051] In step 5 of this embodiment, the 4-nitro-o-phenylenediamine in step 5 of Example 1 is replaced with equimolar 4-methyl-o-phenylenediamine, and the other steps are the same as in Example 1 to obtain N- Methyl-substituted benzimidazole side fluorine liquid crystal compound 0.44g, yield 15%, its chemical name is 2-(2-fluoro-4-((4-(pentyloxy)phenyl)ethynyl)phenyl)- 1,6-Dimethyl-1H-benzimidazole.
[0052]
[0053] The resulting spectral data is as follows:
[0054] IR(KBr)v(cm -1 ): 2939, 2870, 2355, 2203, 1608, 1510, 1337, 1250, 1208, 831, 743, 528.
[0055] 1 H-NMR (400MHz, CDCl 3 , TMS) δ (ppm) = 7.73-7.70 (m, 1H), 7.69-7.66 (m 1H), 7.49-7.45 (d, J = 9.6Hz, 2H), 7.45-7.41 (m, 1H), 7.36- 7.27(m,2H),7.20-7.12(m,1H),6.92-6.86(d,J=9.6Hz,2H),3.98-3.92(t,2H,),3.76-3.69(m,3H),2.55 -2.48(d,3H),1.82-1.77(m,2H),1.45-1.32(m,4H),0.94-0.84(t,J=5.6Hz,3H).
[0056] MS (MALDI-TOF) m / z: theoretical value 426.23, measured value 425.64.
Embodiment 3
[0058] In step 5 of this example, the 4-nitro-o-phenylenediamine in step 5 of Example 1 is replaced with equimolar o-phenylenediamine, and other steps are the same as in Example 1 to obtain N-methyl-substituted phenylenediamine with the following structural formula 0.42g of imidazole pendant fluoro liquid crystal compound, yield 15%, its chemical name is 2-(2-fluoro-4-((4-(pentyloxy)phenyl)ethynyl)phenyl)-1-methyl -1H-benzimidazole.
[0059]
[0060] The spectral data of the product are as follows:
[0061] IR(KBr)v(cm -1 ): 2937, 2866, 2206, 1876, 1608, 1460, 1248, 1116, 1025, 828, 750, 629.
[0062] 1 H-NMR (400MHz, CDCl 3 , TMS) δ (ppm) = 8.43-8.36 (m, 1H), 8.31-8.20 (m1H), 7.91-7.79 (d, J = 7.2Hz 1H), 7.73-7.66 (m, 1H), 7.51-7.47 ( m,2H),7.47-7.44(m,2H),7.41-7.34(m,1H),6.90-6.85(d,J=10Hz,2H),3.99-3.94(t,J=6.8Hz,2H), 3.86-3.79(s,3H),1.83-1.73(m,2H),1.46-1.32(m,4H),0.95-0.89(t,J=6.4Hz,3H).
[0063] MS (MALDI-TOF) m / z: theoretical value 412.21, measured value 413.13...
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