JPH02292260A - Compound with liquid crystal nature - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R* is alkyl having asymmetric carbon atom; R is straight chain alkyl or alkoxy; X is H or halogen; Y is CidenticalC, CH2-CH2 or of formula II; Z is CidenticalC, CH2-CH2 or of formula III; ring A is of formula IV or V; (n) is 1 or 2). USE:Ferroelectric liquid crystal compounds. Having no other smectic phases in the low temperature region of Sc* phase. PREPARATION:For example, a reaction is made between (A) a 4- alkoxycarbonylphenylacetylene of formula VI derived from 4- alkoxycarbonylbromobenzene and 3-methyl-1-butyne-3-ol and (B) a compound of formula VII formed by reaction between a p-alkoxy (or alkyl)phenol and 6-chloronicotyl chloride to obtain the objective compound of the formula I, where Y is CidenticalC, Z is of formula III ring A is of formula IV.

Description

[Detailed description of the invention] [Industrial application field] No. ■ table (d) The symbols in the table indicate the following.

C: crystalline phase, S^: smectic A phase, Sc*: kylanoresmectic C phase, ch: cholesteric phase. S
x, Sy: Smectic phase other than S^, Sc,
■Biisotropic liquid phase.

[Problem that the invention seeks to solve]

Ferroelectricity is a property expressed in the Sc phase of the liquid crystal phase and several other phases, but the Sc phase is of practical importance.

As shown in Table 1, in many conventional compounds, smectic 4 groups other than the Sc phase often appear in the low temperature range of Sc, which is an obstacle to securing a practical use temperature range. Therefore, a liquid crystal compound that does not exhibit any smectic phase other than the Sc phase in the low temperature range of the Sc* phase is desired.

[Means to solve the problem]

As a result of intensive research from the above viewpoint, the present inventors discovered a compound having no other smectic phase in the low temperature region of the *Sc phase, and arrived at the present invention.

In other words, the present invention... General formula [■] (In the formula, ? is an alkyl group having an asymmetric carbon atom, R is a straight-chain alkyl or alkoxy group, X is a hydrogen atom or a halogen atom, Y is a group II C H2 C H2 one or group one OC-.2 is group one C=
It is a liquid crystalline compound represented by N (C- or -C→ring, n is 0 or 1, respectively).

In the present invention, a liquid crystal composition containing at least one liquid crystal compound represented by the above general formula [I] can also be used.

Typical examples of the compound represented by the general formula [I] include y. -C) By the combination of -, z and n,
It can be divided into the following groups.

(In the formula, R, R and X have the same meanings as above.) R*
Any optically active alcohol having an asymmetric carbon atom can be used as OH, but in consideration of industrial versatility, 2-methylbutyl group, 3-methylbenzene group, etc., which can be obtained at low cost, are used as primary groups. group, 4-methylhexyl group, 5-methylheptinole group. 6-methyloctyl group, 3,7-dimethyloctyl group, etc., and as secondary groups, 1-methylpropyl group, l-methylbutyl group, 1-methylbutyl group, etc.
-Methylbentyl group. Examples include optically active alcohols having 1-methylhexyl/l/ group, 1-methylheptyl/l/ group, 1-methyloctyl group, and the like.

The outline of the method for producing the compound of the present invention is as follows.

CF) CH3 [C) (in the formula, R*, R and X have the same meanings as above, m is O
Or indicates 1. ) [Operations and Effects of the Invention] Since the compound of the present invention has no other smectic phase in the low temperature range of the SC phase, it is an important compound in obtaining a practical temperature range of the SC* phase including room temperature. It is expected that this will happen.

〔Example〕

The present invention will be explained below with reference to Examples, in which % indicates weight %.

0 CH3 In a 500 CC trifluorotube equipped with a stirrer, a thermometer and a reflux condenser, 54 mmol of 4-alkoxysulfonylprobenzene, 3-methynole-1-phthine-3 in a nitrogen stream were added. -Oh
Nore 5.91 9 (70 mmol)
, triphenylphosphine 270 mi. Dichlorbis(triphenylphosphine)palladium catalyst K
140■ (0.20 m+nol) and 59 ml of triethynoleamine were charged, stirred and dissolved, and copper iodide 45
Added a cape. After stirring at room temperature for 3 hours, gradually heated to 30
It took several minutes to bring the internal temperature to 80°C. The reaction was allowed to proceed at this temperature for 10 hours. After the reaction, the temperature was returned to room temperature, and triethylamine was distilled off under reduced pressure. 300 ml of ether was added to the residue, washed with water, and dried over anhydrous sodium sulfate. After 500 p, the ether was distilled off, and the residue was subjected to silica gel force column chromatography (200 mesh silicage/L' 100 f.Developing solvent: dichloromethane) to obtain a compound of the following formula (A
) was obtained as an intermediate compound.

CH3 300cc equipped with stirrer, thermometer and distillation equipment. In a three-necked flask, the above compound [A) 57.
8 mmo+, 120 ml of anhydrous toluene, and 200 ml of sodium hydride (60% Nudur dispersant) were charged, and the mixture was stirred at room temperature for 30 minutes. Heat gradually, 30
It took several minutes to bring the internal temperature to 70°C. Reflux of acetone (by-product) begins. Distillation started together with tonoleene, but the reaction continued until the distillation temperature reached the boiling point of tonoleene by further heating. During this period, it took 2 hours and the solvent distilled out was 60 m
It was l. After the reaction is complete, return to room temperature and add benzene 100
m4 was added, washed with water, and dried over anhydrous sodium sulfate. :P
After that, the organic solvent was distilled off, and the residue was purified by silica gel I column chromatography (200 mesh silica gel/l' 100 f. developing solvent: Hensen) and washed with 4-7 in Table 3. Lucoxylponylphenylacetylene [s:) was obtained in a yield of 85-88%. Its structure was confirmed by IR and NMR spectrum.

The results are shown in Table 2.

2nd Production Example 2 Alk/L/-6-chlornicotinic acid ester (Note 1) There is an absorption peak based on C=C at 2100 to 2150 cm, but it is extremely weak.

In a 100 CC three-neck flask equipped with a stirrer, a thermometer, and a reflux condenser, 15 mtnol of optically active alcohol or optically active alkoxylponylphenol and 10 ml of pyridine were dissolved. To this pyridine solution, 7 mmol of 6-chlornicotinic acid chloride dissolved in 20 ml of dichloroethane was added under ice cooling, and after the mixture was brought to room temperature, it was further stirred for 24 hours.

Dichloroethane and pyridine were distilled off under reduced pressure, and the residue was dissolved in 100 ml of ether, washed with a 10% aqueous NaOH solution, and dried over anhydrous sodium sulfate. After passing through the furnace, the ether was distilled off, and the residue was subjected to silica gel force column chromatography (200 mesh silica gel 100?. developing solvent: codichloromethane), using
L/-5-chlornicotinic acid ester CD] was obtained in a yield of 90 to 98%.

The results are shown in Table 3.

Production ifl example 3 p-anolekoxy (or alkyl)
V) Phenyl-stirrer. In a 100 CC three-necked flask equipped with a thermometer and a reflux condenser, p-alkoxy (or alkyl) phenol/I/30 + nmol and 20 ml of anhydrous pyrisine were charged and dissolved under stirring. In this pyricin solution. 6-chlornicotini ~ chloride 35 m
50 ml of a dichloroethane solution containing mo+ was added under water cooling.

After the reaction temperature was returned to room temperature, it was heated to 40°C and stirred for 8 hours. After the reaction was completed, benzene was added, and the mixture was washed with water, anolekali with 10% caustic soda, and water in this order, and then dried over anhydrous sodium sulfate.

The solvent was distilled off under reduced pressure, and the residue was isolated and purified from ethanol to obtain p-alkoxy (also haanolekyl)fe-nole-6-chlornicotinic acid entenore [E] shown in Table 4 at 72%.
Obtained in ~95% yield.

All production example 3 except for using phenol 3Qmmol
was synthesized under the same conditions as 4'-7lukoxy-3- in Table 4.
Chlorpheni) L. /-5-chlornicotinic acid ester l) was obtained with an Ill rate of 83%.

The above results are shown in Table 4.

p-Alkoxy (or alkyl)phenol 30 mm
In place of 4-alkoxy-3-chlor, 4-alkoxy-3-fluorophenyl (Table 1) Production Example 5 4-alkoxy-3-fluorophenyl The reaction temperature was set to 90°C, and the raw material halide was converted to 4-alkoxy-3-fluorophenyl bromide. The reaction was carried out under the same conditions as in Production Example 1 except for this, to obtain a compound CG of the following formula as an intermediate compound.

CHs The above 4-(4-alkoxy-3-fluorophenyl)-2-methyl-3-butine-o/'CG) was added to a 200 CC three-neck flanco equipped with a stirrer, a thermometer, and a distillation device in a nitrogen stream. 9 mmo+, 100 ml of anhydrous toluene, and 100 ml of sodium hydride (60% Nujol dispersant) were charged and stirred at room temperature for 30 minutes. The mixture was heated gradually until the internal temperature reached 70°C over 30 minutes. Acetone (a by-product) began to reflux9 and began to be distilled out together with toluene, but the κ reaction continued with further heating until the distillation temperature reached the boiling point of toluene. This took 2 hours, and the solvent distilled out was 5Q ml. After the reaction is complete,
The temperature was returned to room temperature, 100 ml of benzene was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. After furnace filtration. The organic solvent was distilled off, and the residue was subjected to silica gel column chromatography (20
0 mesh silicage/l/100F. Developing solvent: hexane) to obtain 4-alkoxy-3-fluorophenylacetylene [F] shown in Table 5 in a yield of 80 to 97%. Its structure was confirmed by IR and NMR spectroscopy.

The results are shown in Table 5 along with the properties and physical properties of each compound obtained.

Example 1 Anoleki-6-(Synthesis of p-alfoxyphenyl) In a three-neck IOOCC flask equipped with a stirrer, a thermometer, and a reflux condenser, in a nitrogen stream, optically active alkyl obtained in Production Example 2) V-5 -chlornicotinic acid ester (D:
I 23.3 mmo! , 4-monosubstituted phenylacetylene23. 3 mtool, ? 100 μl of liphenylphosphine, 60 μl of dichlorbis(triphenylhonuphine) palladium catalyst, and 50 μl of triethylamine.
Add t and stir to dissolve. 20~ of copper iodide was added. After stirring at room temperature for 2 hours, the mixture was gradually heated to bring the internal temperature to 80°C over 30 minutes. The reaction was allowed to proceed at this temperature for 16 hours.

After the reaction, the temperature was returned to room temperature, and triethylamine was distilled off under reduced pressure. 100 mt of ether was added to the residue, washed with water, and dried over anhydrous sodium sulfate. After evaporation, the ether was distilled off and the residue was subjected to silica gel column chromatography (200
Mesh silicage/' 100? , developing solution K: dichloromethane) for isolation and purification. Recrystallized from petroleum ether to give the alkynoles of Table 6 (6-Cp-alkoxyphenylethini) V) nicotinic acid esters (I
a,l (X=H) was obtained in 71-80% yield. The structure of each compound was confirmed using IR and NMR spectrum data.

Example [Compound NllL8] Yield 80% IR: ν""
'(z-')2920.2216,1714.1268
, 1246. 832.

NMR: δ Real 33 (ppm) 9.1 (d.LH)
．． 8.2 (dd, LH), 7.5 (Irl, 3
H). 6.8 (In, 2H) ,4.3(
t, 2H). 3.9 (4,2H), 2.2 ~0.
Synthesized under the same conditions as Example 1 except that 4-alkoxy-3-fluorophenylacetylene [F] obtained in Production Example 4 was used instead of 5(m,36-37H)4-monosubstituted phenylacetylene. and Alki/L'-6 in Table 6
-(4-alkoxy 3-funoleorophenylethini)
V) Nicotinic acid entenore (Ial) was obtained in 79% yield.

example. [Compound Nfi5] Yield 79% 1R:vm. x
(crn) 2924.2216.1710.
1272.1116,780.

NMR: a'4:3 (ppm) 9.2 (d, IH
). 8.3 (ddl IH). 7.7 ~ 6.8 (
m. 4H), 4.3 (d. 2H), 4.1
(t, 2H), 2.3 to 0.67 (m. 28H).

The phase transition temperatures of the compounds obtained in Examples 1 and 2 are shown in Table 6.

Example 3 p-alkoxy (or alkyl/I/) phenyl-6 obtained in Production Example 3 was placed in a three-necked flask equipped with a stirrer, a thermometer, and a reflux condenser. - Chronorenicotinic acid ester/L/ 4.8 mmol 4- obtained in T production example 1
Alkoxyluponylphenylacetylene 5. 0 m
+nol, triphenylhonuphine 60■, dichlorbis(triphenylphosphine)palladium catalyst 30
(1) and 3Q ml of human ethylamine were added, stirred and dissolved, and 6~ of copper iodide was added. After stirring at room temperature for 2 hours under a nitrogen atmosphere, the mixture was heated and reacted at 80° C. for 16 hours.

After the reaction, the temperature was returned to room temperature, and triethylamine was distilled off under reduced pressure.
Ether was added to the residue, washed with water, and dried over anhydrous sodium sulfate. After passing through the furnace, ether is distilled off. The residue was isolated and purified by silica gel force column chromatography (200 mesh silicage/L/100 F. developing solvent: dichloromethane). p-Anolekyl or anolekoxyphenyl-6-(1
) 1 Anorekoxica 7Lzhonylphenynorethini/I
/) Nicotine H x Sy tv (Ib) 71-8
Obtained with a yield of 2%. The structure of each compound was confirmed by IR and human NMR spectrum data.

example. [Compound N [116] Yield 77% IR: ti
KB'"sk(m-') 2924, 2220, 173
2,1718,1704.1290.770 0 NMR: δ': 3 (ppm) 9.4 (d.LH)
', 8.4 (dd, LH). 8.1 (d.2H).
7.7 (In, 3H). 7.0 (m, 4H). 5
．． 2 (m, I!{), 4.0 (t, 2H),
2.2-0.7 (m, 31-32H).

Synthesis of nicotinic acid ester (Ib) (x=cz) 4-alkoxy-3-chlorophenyl obtained in Production Example 4 in place of p-alkoxy (or alkyl/V)pheni/l/-6-chlornicotinic acid ester 6ya) v Nicotinic acid ester was synthesized under the same conditions as in Example 3, and the 4-anolekoxy-3-chlorophenyl v-6-(p-7rukoxyl phenyl ethyl Nicotinic acid ester (Ibl) was obtained in a yield of 77%. The structure of the compound was confirmed by rR and NMR spectroscopy.

example. [Compound No. 19] Yield 77%? R: νlIl■ (mouth) 2928. 222 sails 1740, 1698, 1286, 770. NMR: δTMs” (ppm) 9.3 (d, IH
). 8.4 (dd, IH), 8.0 (d, 2H).
7.7 (m, 3a), 7.4 ~ 6.7 (m, 3H
), 5.2(+n.1}{),4.0(t.
2H), 2.2 ~ 0.5 (In. 35 ~
36H).

The phase transition temperatures of the compounds obtained in Examples 3 and 4 are shown in Table 7.

(F) The symbols in Table 7 indicate the following.

C: crystalline phase, Sc: kylanoresmectic C phase S^:
Numectic phase, ch: Cholesteric phase, I
Diisotropic liquid phase, *: asymmetric carbon atom.

Synthetic stirrer. Three-neck Flanuco K. with thermometer and reflux condenser. 4-alkoxyluponylphenylacetylene-6-chlornicotinic acid ester 4.8 mmo+, 4-7-lucoxyphenylacetylene 5.0 mmol, }rifenylrefosphine 60~, cyclobis(triphenylhonuphine) palladium ester n30my& Add 3Q ml of triethylamine, stir and dissolve, and add 6 ml of copper iodide.
■Added. After stirring for 2 hours at room temperature under nitrogen atmosphere, 80
℃ and allowed to react for 16 hours. After the reaction, the temperature was returned to room temperature, triethylamine was distilled off under reduced pressure, ether was added to the residue, washed with water, and dried over anhydrous sodium sulfate. After passing through the furnace, the ether was distilled off and the residue was subjected to silica gel column chromatography (200 mesh silica gel #100).
y, developing solvent: dichloromethane) for isolation and purification. Recrystallize from hexane and 4-(p-
7-carponylphenyl)oxycarponylphenyl-6-(p-7~koxycarbonylphenyl)
Nicotinic acid ester (Icl) was obtained in a yield of 65-84%. The structure of each compound was confirmed by IR and NMR spectrum/reader.

example. [Compound N [L32] Yield 69% Summer R: ν
mlIX ('fut) 2924.
2216. 1736, 1714, 1276.
834 NMR: a Tus 3 (ppm) 9.3 (
”, IH), 8.4 (dd, LH), 8
．． 1 (d. 2H), 7.8 ~ 7.2 (
In. 5H), 6.9(d, 2H). 5.2 (In
, IH). 4.0 (t, 2H). 2.3
~0.5 (In, 35-36H).

Synthesis was carried out under the same conditions as in Example 5 except that 4-alkoxy-3-fluorophenyl acetylene, which was prepared by Wp in Production Example 5, was used in place of 4-anolekoxyphenylene/reaacetylene, and 4' in Table 8 was used. -(p-7 hydroxycarponylphenyl/I/)oxycarponylphenyl/''-6-(4-
Alkoxy-3-fluorophenylethini/V) nicotinic acid entel (Ic) t Obtained in a yield of 65-71%. The structure of the compound was confirmed by IR and NMR spectral data.

example. [Compound Nl33:] Yield 65% 8.1 (d,
2H). 7.7 ~ 6.7 (m.6H), 5.2 (
m, IH), 4. Ht, 2H), 2.2 ~ 0.7
(tn. 35-36H).

The phase transition temperatures of the compounds obtained in Examples 5 and 6 are shown in Table 8.

IR:a,,,! (crn) 2924,22
12.1742,1710,1282,774,762
.

NMR: a, M83Cppm) 9.3 (d, IH)
, 8.4 (dd.IH), (d) The symbols in Table 8 indicate the following.

C, C,: Crystal phase *SC: Chiral numectic C phase.
SA: smectic A phase, ch: cholesteric phase, ■=isotropic liquid phase, *: asymmetric carbon atom.

In a flask equipped with a stirrer, a thermometer, a reflux condenser, and a rubber balloon containing hydrogen scum, the alkyl/l/-6-[p-anolekoxy (or 4-alkoxy-3) obtained in Example 1 or 2 was placed. -Fluoro)phenylethynyl]nicotinic acid ester/' [Ia) 4 mmo+, 200 my of 5% palladium-carbon catalyst, 10 ml of benzene, and 3Q ml of ethyl acetate were charged, and after replacing the hydrogen gas, the mixture was allowed to react at room temperature. The progress of the reaction was examined using a bed chromatograph. The reaction is almost completed in about 1.5 hours, but after 0.5 hours.
The reaction continued in a hydrogen atmosphere for 5 hours. After heating, remove the catalyst using a glass finoletter lined with a furnace aid. The solvent was removed under reduced pressure. The reaction crude product was subjected to silica gel column chromatography (200 mesh silica gel 502
, developing solvent: dichloromethane).
-alkoxy-3-fluoro)phenylethyl]nicotinic acid ester [■d] was obtained in a yield of 90-97%. The structure of each compound was confirmed by IR and NMR spectra.

Example 1. [Compound Nll38:] Yield 90% 1R,,
film(crn-1) 2928. 1920
, 1286.1246, 824.

NMR: a'::3 (ppm) 9. l(d.lH)
．． 8. l(dd.LH). 7.3 ~ 6.5 (In,
5H). 5.1 (In, LH), 3.9
(t.2H). 3.1 (In.4H), 2.2 ~
0.5 (In, 35-36H) Example 2, [Compound No. 37] Yield 92% rR + ν"m (crn-'
) 2928. 1724. 1274,1
122. 804.

CDC73 NMR: δTM8 (ppm) 9.2 (d.L
H), 8.2 (dd, LH), 7.1 to 6.7 (+n
．． 4H), 4.2(d,2H). 4.0(t,2
H). 3.1 (m, 4H), 2.2 ~ 0.5
(In, 28H) Table 9 shows the phase transition temperature of each compound obtained.

Example 8 Example 7 of p-alkoxy (or alkyl/I/) phenyl-6-(p-alkoxy (or 4-
alkoxy-3-fluoro)phenylethynyl] nicotinic acid entel CIa) instead of p-alkoxy (or alkyl)V) phenyl/I/-6-(p-
p-alkoxy (or alkyl/L/) phenyl) V − 5-(p-alkoxyluponinolephenylethyl)nicotinic acid ester (Ie) was obtained in a yield of 90-97%.

The structure of each compound was confirmed using IR and NMR spectral data.

example. [Compound NIl46] Yield 95% IR:vKB
'd''k<cm') 292B+ 1734.17
14.1280,852,768.

NMR: a':: (ppm) 9.2 (d, IH).
8.2 (dd, IH). 7.9 (d, 2H),
7.3 ~ 6.8 (m, 7H), 5, 1 (m, lH),
3.9 (t, 2n), 3.2 (S. 4H
)． 2.1-0.6 (m. 31-32H).

4 obtained in Example 4 in place of the alkyl/l/-6-(p-alkoxy (or 4-alkoxy-3-fluoro) phenylethynyl) nicotinic acid endenole [Ia] of Example 7
-Alkoxy-3-chlorophenyl-6-(p-alkoxycarponylphenylethini)V) Synthesized under the same conditions as in Example 7 except for using nicotinic acid ester (Ib), and the 4-alkoxy- 3'-Chlorphenylene/l/-6-(p-7norecoxylponylphenylethyl/L/)nicotinic acid ester Cie] 9
Obtained in yields of 2-93%. Compound structure Hill and NM
Confirmed with Rsubek/Redata.

example. [Compound order 49] Yield 93% IR: vK""jk (cm-') 2924,
1738. 1700, 1288.788.76
2 o NMR: Yuken 3 (ppm) 9.3 (d.IH), 8
．． 3 (dd.LH). 7.9 (d, 2H), 7.3
~6.8 (m, 6H). 5.1 (+n, LH). 4.
0 (t.2H). 3.2 ($, 4H), 2.2-0
．． 5 (In, 35-36H).

Table 10 shows the phase transition temperatures of the compounds obtained in Examples 8 and 9.

Practical Example 10 4-(p-7 Ruponylphenyl) Example 1, [Compound Nl62] Yield 94% F)
Synthesis of Example 5 or 6 in place of the alkyl/l/-5-[p-alkoxy (also H4-anolekoxy 3-fluoro) phenylethynyl] nicotinic acid ester [Ia] of Example 7
4-(p-alkoxy(or 4-alkoxy-3-fluoro)phenylphenyl)oxycarponylphenyl/l/-6-[:p-alkoxy(or 4-alkoxy-3-fluoro)phenylphenyl]nicotinic acid ester 7y(ic :) was synthesized under the same conditions as in Example 7 except that L. Table 11, 4-(
p-alkoxylponylphenyl/V)oxycarbonylphenyl/l/-6-Cp monoalkoxy (or 4-alkoxy-3-fluoro) phenylethynole] nicotinic acid ester [■f] 91-95% yield I got it. The structure of each compound was confirmed using IR and NMR spectral data.

IR: ν”””k(crn-1) 2920+ 17
38. 1722, 1282.814, 758
.

NMR: δ0Dc'3 (ppm) 9.3 (d.LH
). 8.4-8.0 (+n, 3H), TMS 7.5-6.7 (In, 7H). 5.2
(In. LH). 3.9 (t, 2H). 3.1
(m.4H). 2.2 ~ 0.7 (In, 35 ~ 3
6H).

Example 2. [Compound NQ63] Yield 93% IR:
v”' ”’k(crn”) 2920, 1738,
1710, 1282, 760 oNMR: δTM, 3
mn) 9.3 (a, IH). 8.5～
8.0 (In. 3}{) . 7.5 ~ 6.7 (I
n, 6H). 5.2(m, 11{), 4.0(
t. 2H), 3.1 (In.4H). 2.2 ~0
．． 6 (In. 35-36H).

Table 11 shows the phase transition temperature of each compound obtained.

(stomach) C in Table 11, C+, The symbols SC*, S^ and ■ are It has the same meaning as Table 8.

Claims (1)

[Claims] 1 General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼R[I] (In the formula, R^* represents an alkyl group having an asymmetric carbon atom, R
is a straight-chain alkyl or alkoxy group, X is a hydrogen atom or a halogen atom, Y is a group -C≡C-, a group -CH_2CH
＿２− or group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, Z
is the group -C≡C-, the group -CH_2CH_2- or the group ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼A liquid crystal compound represented by a ring (n represents 0 or 1, respectively).