CN1127465C - Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof - Google Patents

Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof Download PDF

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CN1127465C
CN1127465C CN 00125736 CN00125736A CN1127465C CN 1127465 C CN1127465 C CN 1127465C CN 00125736 CN00125736 CN 00125736 CN 00125736 A CN00125736 A CN 00125736A CN 1127465 C CN1127465 C CN 1127465C
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diphenyl
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CN1293180A (en
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闻建勋
刘克刚
李衡峰
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Shanghai Institute of Organic Chemistry of CAS
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Abstract

The present invention relates to a dual-diphenylacetylene compound containing fluorine, which has the molecular formula as the right upper figure, wherein R or R'=C<1 to 12> alkyl radicals; n=0 to 4; A or B is the right lower figure. The present invention is prepared by a Heck reaction or a condensation reaction. The compound has the characteristics of wide liquid crystal phase transition temperature, low viscosity, high birefringence rate, anisotropy, high cleaning point, etc., and furthermore, the compound is new liquid crystal material.

Description

Fluoric bis(diphenyl)acetylene compound, Preparation method and use
The present invention relates to a kind of fluorine-containing two two benzene-like compounds.This compound bilateral all connects the compound of alkoxyl group.This compound can make respectively by Heck reaction or condensation reaction, is a kind of novel liquid crystal material.
Liquid crystal material needs low melting point, high clearing point, and the mesomorphic phase wide ranges, high birefringence rate, viscosity is low, and is fat-soluble good.Tachibana, Tamon have reported a kind of bis (diphenyl) acetylene nematic phase type liquid crystalline cpd (Jpn.Kokai Tokkyo Koho JP 10130188 A2 19 May 1998), and its principal character is that an end is an alkyl, and the other end is the alkoxyl group side chain.People such as C.S.Hsu reported the bis (diphenyl) acetylene liquid crystalline cpd that utilizes Heck reaction to synthesize to contain the alkyl side chain (Liquid Crystals, 2000, Vol.27, No.2 283-287) is characterized in that two ends are alkyl chain, side direction is the short carbon chain alkyl.We introduce fluorine atom on the basis of two acetylene bond characteristics and tetrafluoro phenyl ring feature primitive has reduced fusing point, have increased nematic temperature range.Because the increasingly extensive application of liquid crystal material, people still expect constantly to explore the liquid crystal material of excellent property.
The purpose of this invention is to provide a kind of new fluoric bis(diphenyl)acetylene compound.Bilateral at compound connects alkoxyl group respectively.
Another object of the present invention provides the method for preparing above-claimed cpd.
Purpose of the present invention also provides above-claimed cpd to be used for the purposes of liquid crystal material.
Fluoric bis(diphenyl)acetylene compound of the present invention has following molecular formula: R or R '=C wherein 1-12Alkyl, n=0-4, A or As following compound:
Figure C0012573600033
Figure C0012573600034
Figure C0012573600041
The fluoric bis(diphenyl)acetylene compound of invention can be made respectively by Heck reaction or condensation reaction, further describes as follows:
The fluorine-containing (diphenyl) acetylene compounds that contains bis-alkoxy of the present invention, can by molecular formula be RO-B-C ≡ CH the palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds and molecular formula be I or Iodide or bromide make through Heck reaction, and reaction formula is: RO-B-C ≡ CH+I or
Figure C0012573600043
Wherein R, R, n and A and B are all ditto described.
Specifically, above-mentioned palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds, halogenide is at palladium compound, CuX and amine organic solvent exist down, in room temperature to reflux temperature, reaction 0.5-100h, the above-claimed cpd mol ratio is followed successively by 1: 1-10: 0.01-0.2: 0.02-0.40: 0-100.Described palladium compound is two (trihydrocarbyl phosphine) dihalide palladium, two (trihydrocarbyl phosphine) palladium, and two (trihydrocarbyl phosphine) Palladous nitrate, described amine organic solvent is to have C 1-12The tertiary amine of alkyl, secondary amine, primary amine, pyridine, bipyridine etc.The having of amine organic solvent helps the carrying out that react, and the mol ratio of above-mentioned halogenide and amine organic solvent is recommended as 1: 1-10, recommend to use triethylamine.
Fluoric bis(diphenyl)acetylene compound of the present invention is simple synthetic method not only, and is a kind of good STN and TFT liquid crystal display material.Have low melting point, high clearing point, the mesomorphic phase wide ranges, the chemical stability height, the degree of birefringence height, characteristics such as response speed is fast are suitable for suitability for industrialized production and application.
The present invention will be helped to understand by following embodiment, but content of the present invention can not be limited.
Embodiment 1
Figure C0012573600051
Preparation: will Or I200mg,
Figure C0012573600053
100-200mg, two (triphenylphosphine) Palladous chlorides or palladium 5-15mg, CuI10-20mg, triethylamine or Di-Octyl amine 5-20ml stir 10-24h in room temperature to 70oC, high pressure liquid chromatography or fluorine spectrum track to reaction and finish, filter, add organic solvent extraction, the organic phase dried over sodium sulfate, boil off solvent, column chromatography for separation.The result is as shown in the table:
Sequence number R Productive rate %
1 2 3 4 5 C4H9 C5H11 C7H15 C8H17 C12H25 70 67 71 69 63
Compound 1: 1HNMR (CDCl 3/ TMS) δ H7.53-6.87 (m, 10H), 3.98 (t, 4H, J=5.3Hz), 1.98-0.87 (m, 16H) ppm. 19FNMR (CDCl 3/ TFA) δ F 30.6 (m, 2F) ppm. MS (m/z, %): 472 (M +, 15.55), 109 (100.0). ultimate analysis: theoretical (%) C78.79 H6.40 F8.04. actual measurement (%) C78.85H6.50F7.63. compound 2: 1HNMR (CDCl 3/ TMS) δ H7.57-6.33 (m, 10H), 3.98 (t, 4H, J=5.7Hz), 2.02-0.73 (m, 18H) ppm. 19FNMR δ F30.7 (m, 2F) ppm.MS (m/z, %): 486 (M +, 100.0). ultimate analysis: theoretical (%) C78.99 H6.63 F7.81. actual measurement (%) C79.15 H6.74 F7.54 compound 3: 1HNMR (CDCl 3/ TMS) δ H7.47-6.84 (m, 10H), 4.00 (t, 4H, J=5.9Hz), 2.00-0.85 (m, 22H) ppm. 19FNMR (CDCl 3/ TFA) δ F31.0 (m, 2F) ppm.MS (m/z, %): 514 (M +, 100.0). ultimate analysis: theoretical (%) C79.35 H7.05 F7.38. actual measurement (%) C79.53 H7.21 F7.16. compound 4: 1HNMR (CDCl 3/ TMS) δ H7.57-6.80 (m, 10H), 3.99 (t, 4H, J=5.9Hz), 1.99-0.85 (m, 24H) ppm. 19FNMR (CDCl 3/ TFA) δ F31.0 (m, 2F) ppm.MS (m/z, %): 528 (M +, 100.0). ultimate analysis: theoretical (%) C79.52 H7.24 F7.19. actual measurement (%) C79.60 H7.22 F7.18. compound 5: 1HNMR (CDCl 3/ TMS) δ H7.50-6.80 (m, 10H), 4.01 (t, 4H, J=5.9Hz), 2.02-0.65 (m, 32H) ppm. 19FNMR (CDCl 3/ TFA) δ F30.8 (m, 2F) ppm.MS (m/z, %): 584 (M +, 100.0). ultimate analysis: theoretical (%) C 80.10 H7.93F6.50. actual measurement (%) C79.97 H7.89 F6.59
Embodiment 2
Figure C0012573600061
Preparation will Or I 200mg, 100-200mg, two (triphenylphosphine) Palladous chloride 5-15mg, CuI 10-20mg adds triethylamine or pyridine 10mL, stirs 10-24h in room temperature to 70oC, and product concentrates through column chromatography for separation.The result is as follows:
Sequence number R Productive rate %
6 7 8 9 10 11 CH 3 C 4H 9 C 5H 11 C 6H 13 C 7H 15 C 8H 17 76 72 70 80 68 73
Compound 6 1HNMR (CDCl 3/ TMS) δ H7.42-6.80 (m, 6H), 4.34 (s, 3H), 4.00 (t, 2H, J=5.5Hz), 2.01-0.75 (m, 9H) ppm. 19FNMR (CDCl 3/ TFA) δ F29.6 (m, 2F), 60.0 (m, 2F), 79.9 (m, 2F) ppm.MS (m/z, %): 502 (M +, 56.78), 418 (100.0). ultimate analysis: theoretical (%) C66.93 H4.01 F22.69. actual measurement (%) C66.85 H4.15 F22.60. compound 7 1HNMR (CDCl 3/ TMS) δ H7.52-6.85 (m, 6H), 4.31 (t, 2H, J=5.8Hz), 4.00 (t, 2H, J=5.5Hz), 2.01-0.75 (m, 16H) ppm. 19FNMR (CDCl 3/ TFA) δ F29.8 (m, 2F), 59.7 (m, 2F), 79.7 (m, 2F) ppm.MS (m/z, %): 544 (M +, 56.77), 418 (100.0). ultimate analysis: theoretical (%) C68.38 H4.81 F20.93. actual measurement (%) C68.53 H4.72 F20.72. compound 8 1HNMR (CDCl 3/ TMS) δ H7.56-6.90 (m, 6H), 4.34 (t, 2H, J=5.8Hz), 4.03 (t, 2H, J=5.7Hz), 2.03-0.80 (m, 18H) ppm. 19FNMR (CDCl 3/ TFA) δ F29.7 (m, 2F), 60.2 (m, 2F), 80.0 (m, 2F) ppm.MS (m/z, %): 558 (M +, 56.77), 418 (100.0). ultimate analysis: theoretical (%) C68.81 H5.05. actual measurement (%) C68.63 H5.15. compound 9 1HNMR (CDCl 3/ TMS) δ H7.50-6.83 (m, 6H), 4.27 (t, 2H, J=5.9Hz), 3.98 (t, 2H, J=5.4Hz), 1.92-0.72 (m, 20H) ppm. 19FNMR (CDCl 3/ TFA) δ F29.5 (m, 2F), 60.0 (m, 2F), 79.9 (m, 2F) ppm.MS (m/z, %): 572 (M +, 56.13), 418 (100.0). ultimate analysis: theoretical (%) C69.22 H5.28 F19.91. actual measurement (%) C68.99 H5.25 F20.40. compound 10 1HNMR (CDCl 3/ TMS) δ H7.54-6.87 (m, 6H), 4.30 (t, 2H, J=5.6Hz), 3.99 (t, 2H, J=5.4Hz), 1.97-0.75 (m, 22H) ppm. 19FNMR (CDCl 3/ TFA) δ F29.8 (m, 2F), 59.9 (m, 2F), 80.0 (m, 2F) ppm.MS (m/z, %): 586 (M +, 73.48), 418 (100.0). ultimate analysis: theoretical (%) C69.62 H5.50 F19.43. actual measurement (%) C69.74 H5.42 F19.61. compound 11 1HNMR (CDCl 3/ TMS) δ H7.53-6.86 (m, 6H), 4.30 (t, 2H, J=5.4Hz), 4.00 (t, 2H, J=5.8Hz), 1.94-0.77 (m, 24H) ppm. 19FNMR (CDCl 3/ TFA) δ F30.0 (m, 2F), 60.3 (m, 2F), 80.4 (m, 2F) ppm.MS (m/z, %): 600 (M +, 67.68), 418 (100.0). ultimate analysis: theoretical (%) C69.99 H5.71 F18.98. actual measurement (%) C70.11 H5.79 F19.25.
Embodiment 3
Figure C0012573600071
Preparation: adopt
Figure C0012573600072
Or I and
Figure C0012573600073
Be raw material, operation is with embodiment 1, and the result is as follows:
Sequence number R Productive rate %
12 13 14 15 16 C 4H 9 C 5H 11 C 6H 13 C 7H 15 C 8H 17 63 68 59 58 64
Compound 12 1HNMR (CDCl 3/ TMS) δ H7.55-6.85 (m, 8H), 4.30 (t, 2H, J=5.3Hz), 4.00 (t, 2H, J=5.8Hz), 2.57-0.80 (m, 16H) ppm. 19FNMR (CDCl 3/ TFA) δ F60.9 (m, 2F), 80.4 (m, 2F) ppm.MS (m/z, %): 508 (M +, 89.67), 382 (100.0). ultimate analysis: theoretical (%) C73.23 H5.51 F14.96. actual measurement (%) C73.44 H5.57 F14.87. compound 13 1HNMR (CDCl 3/ TMS) δ H7.48-6.76 (m, 8H), 4.25 (t, 2H, J=5.2Hz), 3.96 (t, 2H, J=5.9Hz), 2.03-0.73 (m, 18H) ppm. 19FNMR (CDCl 3/ TFA) δ F60.2 (m, 2F), 80.0 (m, 2F) ppm.MS (m/z, %): 522 (M +, 100.0). ultimate analysis: theoretical (%) C73.56 H5.75 F14.56. actual measurement (%) C73.65 H5.88 F14.61. compound 14 1HNMR (CDCl 3/ TMS) δ H7.55-6.80 (m, 8H), 4.23 (t, 2H, J=5.4Hz), 3.93 (t, 2H, J=5.9Hz), 1.95-0.70 (m, 20H) ppm. 19FNMR (CDCl 3/ TFA) δ F60.4 (m, 2F), 80.3 (m, 2F) ppm.MS (m/z, %): 536 (M +, 82.59) and 382 (100.0). ultimate analysis: theoretical (%) C73.87 H6.01 F14.16. actual measurement (%) C73.60 H6.04 F14.27. compound 15 1HNMR (CDCl 3/ TMS) δ H7.57-6.95 (m, 8H), 4.30 (t, 2H, J=5.3Hz), 4.00 (t, 2H, J=5.7Hz), 2.01-0.75 (m, 22H) ppm. 19FNMR (CDCl 3/ TFA) δ F60.8 (m, 2F), 80.6 (m, 2F) ppm.MS (m/z, %): 550 (M +, 13.21) and 57 (100.0). ultimate analysis: theoretical (%) C74.16 H6.22 F13.80 actual measurement (%) C74.25 H6.27 F14.14. compound 16 1HNMR (CDCl 3/ TMS) δ H7.55-6.85 (m, 8H), 4.28 (t, 2H, J=5.3Hz), 3.98 (t, 2H, J=5.8Hz), 1.97-0.60 (m, 24H) ppm. 19FNMR (CDCl 3/ TFA) δ F60.8 (m, 2F), 80.5 (m, 2F) ppm.MS (m/z, %): 564 (M +, 100.0). ultimate analysis: theoretical (%) C74.45 H6.43 F13.46 actual measurement (%) C74.69 H6.13 F13.48.
Embodiment 4
Figure C0012573600091
Preparation: adopt
Figure C0012573600092
With Be raw material, operation is with embodiment 2, and its result is as follows:
Sequence number R Productive rate %
17 18 19 20 C 3H 7 C 6H 13 C 9H 19 C 11H 23 55 57 49 50
Compound 17 1HNMR (CDCl 3/ TMS) δ H7.47-6.78 (m, 6H), 4.20 (t, 2H, J=5.2Hz), 3.95 (t, 2H, J=5.9Hz), 2.05-0.73 (m, 18H) ppm. 19FNMR (CDCl 3/ TFA) δ F56.0 (m, 1F), 60.6 (m, 2F), 80.6 (m, 2F), 81.5 (1F, m) ppm..MS (m/z, %): 558 (M +). ultimate analysis: theoretical (%) C68.81 H5.05 F20.41. actual measurement (%) C68.70 H5.25 F20.11. compound 18 1HNMR (CDCl 3/ TMS) δ H7.49-6.80 (m, 6H), 4.28 (t, 2H, J=5.4Hz), 3.99 (t, 2H, J=5.9Hz), 1.98-0.60 (m, 24H) ppm. 19FNMR (CDCl 3/ TFA) δ F55.7 (m, 1F), 60.9 (m, 2F), 80.4 (m, 2F), 81.8 (1F, m) ppm..MS (m/z, %): 600 (M +). ultimate analysis: theoretical (%) C69.99 H5.71 F18.98. actual measurement (%) C70.11 H5.57 F18.77. compound 19 1HNMR (CDCl 3/ TMS) δ H7.55-6.82 (m, 6H), 4.28 (t, 2H, J=5.3Hz), 4.07 (t, 2H, J=5.7Hz), 1.98-0.65 (m, 30H) ppm. 19FNMR (CDCl 3/ TFA) δ F55.9 (m, 1F), 61.0 (m, 2F), 80.1 (m, 2F), 81.7 (1F, m) ppm..MS (m/z, %): 624 (M +). ultimate analysis: theoretical (%) C71.01 H6.27 F17.74 actual measurement (%) C71.12 H6.08 F17.90. compound 20 1HNMR (CDCl 3/ TMS) δ H7.52-6.75 (m, 6H), 4.27 (t, 2H, J=5.3Hz), 3.99 (t, 2H, J=5.8Hz), 2.05-0.56 (m, 34H) ppm. 19FNMR (CDCl 3/ TFA) δ F55.8 (m, 1F), 60.8 (m, 2F), 80.5 (m, 2F), 81.6 (1F, m) ppm.MS (m/z, %): 670 (M +). ultimate analysis: theoretical (%) C71.62 H6.61 F16.99 actual measurement (%) C71.80 H6.33 F16.80.
Embodiment 5
Figure C0012573600101
Preparation: adopt
Figure C0012573600102
Be raw material, operation is with embodiment 2.Obtain compound 21 with 68% productive rate.Compound 21: 1HNMR (CDCl 3/ TMS) δ H7.74-6.80 (m, 10H), 4.21 (t, 2H, J=5.4Hz), 3.94 (t, 2H, J=5.9Hz), 1.98-0.60 (m, 18H) ppm. 19FNMR (CDCl 3/ TFA) δ F55.8 (m, 1F), 81.7 (1F, m) ppm..MS (m/z, %): 486 (M +). ultimate analysis: theoretical (%) C78.99 H6.63 F7.81. actual measurement (%) C78.91 H6.44 F7.98.
Embodiment 6
Figure C0012573600103
Preparation: adopt Or I and
Figure C0012573600105
Be raw material.Operation makes through the Heck reaction with embodiment 1.Compound 22: 1HNMR (CDCl 3/ TMS) δ H7.52-6.75 (m, 7H), 4.24 (t, 2H, J=5.3Hz), 3.89 (t, 2H, J=5.8Hz), 2.05-0.56 (m, 30H) ppm. 19FNMR (CDCl 3/ TFA) δ F55.9 (m, 1F), 60.6 (m, 2F), 80.6 (m, 2F) ppm.MS (m/z, %): 643 (M +). ultimate analysis: theoretical (%) C70.90 H6.42 F17.71 actual measurement (%) C70.78 H6.33 F17.90.
Embodiment 7 Preparation: adopt Or Br and
Figure C0012573600113
Be raw material.Operation makes through the Heck reaction with embodiment 1.Compound 23 1HNMR (CDCl 3/ TMS) δ H7.23 (m, 2H), 3.89 (s, 6H) ppm. 19F NMR (CDCl 3/ TFA) δ F29.7 (m, 2F), 59.8 (m, 4F), 80.1 (m, 4F) ppm.MS (m/z, %): 518 (M +). ultimate analysis: theoretical (%) C55.62 H1.56 F36.65 actual measurement (%) C55.74 H1.33 F36.50.
Embodiment 8
With orthogonal polarizing microscope the part of compounds of embodiment 1 to 7 is carried out phase research, the phase transition property that in heating and cooling process, occurs.During their transformation behavior was listed in the table below, wherein Cr represented crystal, and N represents nematic phase, and I represents anisotropic liquid, and Recr represents crystallization.The mesomorphic phase scope of this compounds is very wide as can be seen from the table.
The compound sequence number Phase transition property
1 2 3 4 7 8 9 10 11 Cr 115.0 N 214.3 I 212.6 N 110.1 Recr Cr 103.9 N 203.1 I 201.5 N 93.0 Recr Cr 97.8 N 195.4 I 194.1 N 89.4 Recr Cr 94.5 N 191.5 I 190.1 N 82.2 Recr Cr 109.4 N 201.1 I 199.6 N 102.7 Recr Cr 102.5 N 191.8 I 190.5 N 95.4 Recr Cr 101.1 N 186.7 I 185.4 N 95.6 Recr Cr 99.3 N 179.5 I 178.5 N 93.0 Recr Cr 101.8 N 176.1 I 174.4 N 94.8 Recr
12 13 14 15 16 Cr 82.5 N 211.0 I 209.8 N 74.4 Recr Cr 70.2 N 196.8 I 194.6 N 53.9 Recr Cr 70.8 N 196.4 I 195.0 N 62.1 Recr Cr 91.1 N 188.7 I 187.5 N 66.9 Recr Cr 101.4 N 184.5 I 183.4 N 87.0 Recr

Claims (7)

1. fluoric bis(diphenyl)acetylene compound is characterized in that described fluoric bis(diphenyl)acetylene compound has following molecular formula: R or R '=C wherein 1-12Alkyl, n=0-4, A or Or
Figure C0012573600023
, except R is isopentyl, A and B for to perfluorophenyl, n is beyond 0 the compound.
2. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 1, it is characterized in that with by molecular formula be RO-B-C ≡ CH the palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds and molecular formula be I or
Figure C0012573600024
Iodide or bromide, at palladium compound, CuX and amine organic solvent exist down, make through the HecK reaction, wherein R, R ', n and A and B are according to claim 1.
3. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2, it is characterized in that described palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds, iodide or bromide are at palladium compound, CuX and amine organic solvent exist down, in room temperature to reflux temperature, reaction 0.5-100h, described compound mol ratio is followed successively by 1: 1-10: 0.01-0.2: 0.02-0.40: 0-100.
4. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that described palladium compound is two (trihydrocarbyl phosphine) dihalide palladium, two (trihydrocarbyl phosphine) palladium, two (trihydrocarbyl phosphine) Palladous nitrate.
5. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that described amine organic solvent is to have C 1-12The tertiary amine of alkyl, secondary amine, primary amine, pyridine, bipyridine,
6. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that the mol ratio of described halogenide and amine organic solvent is 1: 1-10.
7. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that described amine organic solvent is a triethylamine.
CN 00125736 2000-10-20 2000-10-20 Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof Expired - Fee Related CN1127465C (en)

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US8420235B2 (en) * 2009-06-04 2013-04-16 Nitto Denko Corporation Emissive diaryl acetylenes
DE102011112950A1 (en) * 2010-10-13 2012-04-19 Merck Patent Gmbh Compounds for a liquid-crystalline medium and their use for high-frequency components
CN102603568A (en) * 2011-11-28 2012-07-25 北京科技大学 Fluorine-containing bis-diphenylacetylene liquid crystal compound and preparation method thereof
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