JPH0737403B2 - Optically active biphenyl ether compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an optically active alkylbiphenyl ether compound useful as a ferroelectric liquid crystal compound.

The liquid crystal display devices that are currently widely used are the twisted nematic (TM type) and the dynamic scattering type (DS type). These are displays by a nematic liquid crystal cell whose main component is nematic liquid crystal. One of the disadvantages of conventional nematic liquid crystal cells is the fact that the response speed is slow and only a response speed on the order of a few milliseconds can be obtained, which is one of the reasons for narrowing the range of application of nematic liquid crystal cells. Has become. However, it has recently been found that a higher response can be obtained by using a smectic liquid crystal cell.

It has become clear that some optically active smectic liquid crystals exhibit ferroelectricity, and great expectations are being cut off regarding their use. As the liquid crystal exhibiting ferroelectricity, that is, the ferroelectric liquid crystal, for example, 4- (4
-N-decyloxybenzylideneamino) cinnamic acid-2
-Methylbutyl ester (hereinafter abbreviated as DOBAMBC) is known, and is characterized by exhibiting ferroelectricity in its chiral smectic phase (hereinafter abbreviated as Sc * phase). is there.

In recent years, with the discovery of high-speed response on the order of microseconds in thin film cells of DOBAMBC, ferroelectric liquid crystal utilizes its high-speed response not only for displays such as liquid crystal TVs, but also for optical printers. It is attracting attention as a material that can be used as a material for optoelectronic-related elements such as heads, optical Fourier transform elements, and light valves.

However, since DOBAMBC contains a Schiff base, it is chemically unstable and has not yet been put to practical use.

The object of the present invention is to provide a compound having a novel optical activity which can be used in the above applications.

That is, the compound provided by the present invention is a compound represented by the following general formula.

(In the formula, n represents an integer of 1 to 18, and * represents an asymmetric carbon atom.) The present invention will be described in more detail below.

The compound represented by the above general formula can be easily synthesized, for example, by a well-known etherification reaction such as converting citronellol to a sulfonic acid ester and then reacting it with 4- (4′-alkoxyphenyl) phenol. .

Next, the present invention will be described with reference to examples. However, the present invention is not limited to these examples.

Example 1 Synthesis of (R) -4-citronellyloxy-4'-octoxybiphenyl 3.12 g of citronellol and 3.04 g of triethylamine were dissolved in 30 ml of dichloromethane and cooled to 0 to -10 ° C. Thereafter, 2.99 g of methanesulfonyl chloride was gently added dropwise, and after completion of the addition, the mixture was further stirred at room temperature for 3 hours. 30 ml of dichloromethane was added to the obtained reaction mixture, and the mixture was washed with ice water, 10% hydrochloric acid aqueous solution, saturated sodium bicarbonate aqueous solution and saturated saline. After drying over magnesium sulfate, the solvent was removed to obtain a mesyl ester.

The obtained mesyl ester (4.0 g), 4- (4'-octoxyphenyl) phenol (4.6 g) and caustic soda (1.0 g) were added to dry dioxane (30 ml), and the mixture was stirred under reflux for 6 hours. The precipitate formed was filtered off using Celite at room temperature, and the filtrate was desolvated. The residue was purified by silica gel and recrystallized from hexane to obtain 3.7 g of (R) -4-citronellyloxy-4'-octyloxybiphenyl.

As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorptions and was confirmed to be the target product.

2950, 1640, 1250 and 830 cm ^-1 The optical rotations of the obtained products are shown below.

[Α] _D = 1.86 (C = 1, chloroform solution, 25 ° C.) Example 2 Synthesis of (R) -4-citronellyloxy-4′-hexyloxybiphenyl To 4- (4′-octyloxyphenyl) phenol Instead of using 4- (4'-hexyloxyphenyl) phenol, (R) -4-citronellyloxy-4'-hexyloxybiphenyl was obtained in the same manner as in Example 1.

As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorptions and was confirmed to be the target product.

2950, 1640, 1250 and 830 cm ^-1 The optical rotations of the obtained products are shown below.

[Α] _D = 1.98 (C = 1, chloroform solution, 25 ° C.) This compound was subjected to orientation treatment by rubbing to give a thickness of 2
After injecting into a glass transparent electrode cell of μm, it was heated to 90 ° C. to obtain an isotropic liquid.

This liquid crystal cell was cooled while applying a rectangular wave of 15 V and 1 Hz under orthogonal Nicols, and the phase morphology was observed with a polarization microscope.
The following phase transitions were confirmed.

Example 3 Synthesis of (R) -4-citronellyloxy-4'-decyloxybiphenyl Except that 4- (4'-octoxyphenyl) phenol is replaced with 4- (4'-decyloxyphenyl) phenol. (R) -4-Citronellyloxy-4′-decyloxybiphenyl was obtained in the same manner as in Example 1.

As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorptions and was confirmed to be the target product.

2950, 1640, 1250 and 830 cm ^-1 The optical rotations of the obtained products are shown below.

[Α] _D = 1.80 (C = 1, chloroform solution, 25 ° C.) This compound was subjected to orientation treatment by rubbing to give a thickness of 2
After injecting into a glass transparent electrode cell of μm, it was heated to 90 ° C. to obtain an isotropic liquid.

This liquid crystal cell was cooled while applying a rectangular wave of 15 V and 1 Hz under orthogonal Nicols, and the phase morphology was observed with a polarization microscope.
The following phase transitions were confirmed.

Claims (1)

[Claims] 1. An optically active biphenyl ether compound represented by the following general formula. (In the formula, n represents an integer of 1 to 18, and * represents an asymmetric carbon atom.)