Aromatic ester compound substituted with sulfur-containing fluoroalkane at both ends of molecule, and gelling agent or thickener containing same

Abstract

An object of the present invention is to provide a novel compound which is a low-molecular-weight compound having no hydrogen-bonding functional group in the molecule and which can gel not only a high-dielectric-constant organic solvent (organic electrolytic solution), which has been difficult to gel, but also an ionic liquid and a silicone oil at a low concentration.SOLUTION: The compound of the present invention is an aromatic ester compound represented by the following formula (1). In the formula, Ar1 and Ar2 each independently represent a substituted or unsubstituted divalent aromatic group, a and b each independently represent 0, 1, or 2, m and n each independently represent an integer of 1 to 20, and p and q each independently represent an integer of 0 to 6.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an aromatic ester compound having both molecular terminals substituted with a sulfur-containing fluoroalkane, and a gelling agent or thickener containing the same. [Background technology]

[0002] Gelling agents are used in various industrial fields (e.g., paints, cosmetics, medicine, oil spill treatment, electronics and optics, environmental fields, etc.) to solidify organic liquid substances, i.e., to solidify them into a jelly-like substance or to increase their viscosity.

[0003] Conventionally, organic gelators with low or high molecular weights have been used to immobilize organic liquids. Most of these organic gelators are low molecular weight compounds with hydrogen-bonding functional groups (e.g., amino groups, amide groups, urea, etc.) in the molecule or polymer compounds with a three-dimensional network structure. However, the present inventors have been developing gelators that can gel various organic solvents at low concentrations, and have proposed fluoroalkane derivatives in particular. Patent Documents 1 to 6 describe the following fluoroalkane derivatives. (Patent Document 1) [ka] (α is a hydrogen atom or a hydroxyl group; Ar is a substituted or unsubstituted divalent aromatic group having 5 to 30 aromatic nucleus atoms; R1 is a saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms; m is 6 to 12; and p is 1 to 4). [ka] (R 2 is a saturated or unsaturated divalent hydrocarbon group having 2 to 20 carbon atoms; Ar and m are the same as above; Z is a sulfur atom or an oxygen atom; and q is 0 or an integer of 1 to 4. [ka] (Ar, R 1 , m and q are the same as above) (Patent Document 2) [ka] (m, n, and x are positive integers) (Patent Document 3) C m F 2m+1 R 1 -SO2-ZOR 2 -OZ-SO 2 -R 3 C n F 2n+1 (Z is a substituted or unsubstituted divalent aromatic hydrocarbon group having 5 to 30 ring atoms; R 1 and R 3 is a single bond or a saturated or unsaturated divalent hydrocarbon group having 1 to 10 carbon atoms; R 2 represents a divalent group having two or more substituted or unsubstituted divalent hydrocarbon groups having 2 to 18 carbon atoms and one or more oxygen and / or sulfur atoms; m and n represent natural numbers from 2 to 18. (Patent Document 4) RX-Ar 1 -OR 1 -O-Ar 2 -Y (Ar 1 and Ar 2 represents a substituted or unsubstituted divalent aromatic group having 6 to 30 ring atoms; R 1 represents a saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms which may have an oxygen atom or a sulfur atom in the chain; R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms which has a perfluoroalkyl group; X represents a group represented by -S- or -SO2-; and Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. (Patent Document 5) R 2 -L 1 -Ar 1 -X 1 -R 1 (Ar 1 represents a substituted or unsubstituted divalent aromatic group having 6 to 30 ring atoms; R 1is a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms and containing a perfluoroalkyl group; X 1 is an oxygen atom, a sulfur atom, or a group represented by -SO2-; R 2 is a specific monovalent group; L 1 is R 2 Depending on the type of group, it represents a group represented by -COO- or -OCO-. (Patent Document 6) C m F 2m+1 -(CH2) y -CHX-C n H 2n -O-Ar-OR (X is a hydrogen atom or a halogen atom; when X is a hydrogen atom, y is 0, and when X is a halogen atom, y is 0 or 1; Ar is a substituted or unsubstituted divalent aromatic group having 5 to 30 carbon atoms; R is a saturated or unsaturated monovalent hydrocarbon group having 1 to 20 carbon atoms; m is 6 to 12; and n is 1 to 4.) (Patent Document 7) R 1 -S(O) n -Ar 1 -R (R 1 represents an alkyl group in which 60% or more of the hydrogen atoms are substituted with fluorine atoms or a C1-30 hydrocarbon group having an alkyl group in which 60% or more of the hydrogen atoms are substituted with fluorine atoms; Ar 1 represents an unsubstituted or substituted C3-20 divalent aromatic group; R represents an unsubstituted or substituted C1-30 hydrocarbon group or a group represented by the following formula: -CO-L-Ar 2 -Y 1 (Y 1 represents a cyano group, a nitro group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C1-20 alkylsulfanyl group, an unsubstituted or substituted C1-20 alkylsulfinyl group, or an unsubstituted or substituted C1-20 alkylsulfonyl group; Ar 2 represents an unsubstituted or substituted C3-20 divalent aromatic group; L represents a divalent linking group; a group represented by: (Patent Document 8) [ka] (Ar represents a substituted or unsubstituted divalent aromatic group; y represents 0, 1, or 2; m and n each independently represent an integer from 1 to 20; p and q each independently represent an integer from 0 to 6; and r represents an integer from 1 to 3.) [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO2007 / 083843 Pamphlet [Patent Document 2] WO2009 / 078268 Pamphlet [Patent Document 3] Japanese Patent Application Laid-Open No. 2011-246422 [Patent Document 4] Japanese Patent Application Laid-Open No. 2016-064990 [Patent Document 5] Japanese Patent Application Laid-Open No. 2016-175873 [Patent Document 6] Japanese Patent Application Laid-Open No. 2019-081836 [Patent Document 7] WO2021 / 177334 Brochure [Patent Document 8] Japanese Patent Publication No. 2022-136032 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a novel compound that is low in molecular weight and does not have a hydrogen-bonding functional group in the molecule, and that can gel not only high-dielectric-constant organic solvents (organic electrolytes) that have traditionally been difficult to gel at low concentrations, but also ionic liquids and silicone oils. [Means for solving the problem]

[0006] As a result of intensive research to solve the above-mentioned problems, the present inventors have found that an aromatic ester compound in which both molecular terminals are substituted with a sulfur-containing fluoroalkane can solve the above-mentioned problems, and have thus completed the present invention.

[0007] That is, the present invention includes the following aspects. [1] An aromatic ester compound represented by formula (1): [ka] (In the formula, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted divalent aromatic group, a and b each independently represent 0, 1, or 2; m and n each independently represent an integer of 1 to 20, p and q each independently represent an integer of 0 to 6. [2] Ar in formula (1) 1 and Ar 2 is a substituted or unsubstituted phenylene group, naphthylene group, or biphenylene group. [3] A gelling agent or thickening agent containing the aromatic ester compound according to [1] or [2]. [4] A gel composition comprising the gelling agent or thickener according to [3] and an organic solvent or silicone oil. [Effects of the Invention]

[0008] The aromatic ester compound of the present invention, both ends of which are substituted with sulfur-containing fluoroalkanes, can gel not only high-dielectric-constant organic solvents (organic electrolytes), which have been difficult to gel until now, but also ionic liquids and silicone oils. In addition, because the organogelator does not contain any hydrogen-bonding functional groups, the formed organogel is expected to maintain high (electro)chemical stability. Furthermore, because the amount added is extremely small (5% or less), it is possible to thicken or quasi-solidify the solution while maintaining the solvent's properties, which improves handling. Furthermore, the addition of the compound of the present invention to silicone oil increases the viscosity, and a thickening effect can be expected. Furthermore, by adding the compound of the present invention to silicone oil or ionic liquid, the viscosity does not change before and after shearing, and therefore the compound has thixotropy. [Brief explanation of the drawings]

[0009] [Figure 1] 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compounds of the present invention (1-4-4 and 1-4-6) and 1-octanol. The numbers in the figure indicate the compound numbers. The same applies below. [Figure 2] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compounds of the present invention (2-4-4 and 2-4-6) and 1-octanol. [Figure 3] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and 1-octanol. [Figure 4] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compounds of the present invention (4-4-4 and 4-4-6) and 1-octanol. [Figure 5] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compounds of the present invention (1-4-4 and 1-4-6) and propylene carbonate. [Figure 6] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compounds of the present invention (2-4-4 and 2-4-6) and propylene carbonate. [Figure 7]FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and propylene carbonate. [Figure 8] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound (4-4-6) of the present invention and propylene carbonate. [Figure 9] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (1-4-4, 1-4-6, 1-6-4, and 1-6-6) and [DEME][TFSA]. [Figure 10] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound (2-4-6) of the present invention and [DEME][TFSA]. [Figure 11] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and [DEME][TFSA]. [Figure 12] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (4-4-6 and 4-6-6) and [DEME][TFSA]. [Figure 13] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (1-4-4, 1-4-6, 1-6-4, and 1-6-6) and [BMIM][TFSA]. [Figure 14] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound (2-4-6) of the present invention and [BMIM][TFSA]. [Figure 15] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and [BMIM][TFSA]. [Figure 16] FIG. 1 shows the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (4-4-6 and 4-6-6) and [BMIM][TFSA]. [Figure 17]FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (1-4-4, 1-4-6, 1-6-4, and 1-6-6) and Poly(methylhydrosiloxane). [Figure 18] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (2-4-4, 2-4-6, 2-6-4, and 2-6-6) and Poly(methylhydrosiloxane). [Figure 19] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and Poly(methylhydrosiloxane). [Figure 20] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (1-4-4, 1-4-6, 1-6-4, and 1-6-6) and Poly(dimethylsiloxane). [Figure 21] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (2-4-4, 2-4-6, 2-6-4, and 2-6-6) and Poly(dimethylsiloxane). [Figure 22] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and Poly(dimethylsiloxane). [Figure 23] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (1-4-4, 1-4-6, 1-6-4, and 1-6-6) and Poly(methylphenylsiloxane). [Figure 24] FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (2-4-4, 2-4-6, 2-6-4, and 2-6-6) and Poly(methylphenylsiloxane). [Figure 25]FIG. 1 is a graph showing the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compounds of the present invention (3-4-4, 3-4-6, 3-6-4, and 3-6-6) and Poly(methylphenylsiloxane). [Figure 26] FIG. 1 shows the results of steady flow viscosity measurement and thixotropy measurement for a gel of compound (1-6-6) of the present invention and Poly(methylhydrosiloxane). [Figure 27] FIG. 1 shows the results of measuring the thixotropy of a gel of the compound (1-6-6) of the present invention and a gel of [BMIM][TFSA]. DETAILED DESCRIPTION OF THE INVENTION

[0010] (Aromatic ester compound in which both ends of the molecule are substituted with sulfur-containing fluoroalkanes) The aromatic ester compound of the present invention is a compound represented by the following formula (1).

[0011] [ka]

[0012] In the above formula, Ar 1 and Ar 2 represents a substituted or unsubstituted divalent aromatic group, a and b represent 0, 1 or 2; m and n each independently represent an integer of 1 to 20, p and q each independently represent an integer of 0 to 6;

[0013] Ar 1 and Ar 2The "divalent aromatic group" in the "substituted or unsubstituted divalent aromatic group" specifically refers to a "C3-10 aromatic group." Here, "C3-10" refers to the number of carbon atoms constituting the aromatic group, and in order to satisfy aromaticity, atoms other than carbon, such as oxygen atoms, nitrogen atoms, and sulfur atoms, may be included to form the divalent aromatic group. The aromatic group may be either monocyclic or polycyclic, and as long as at least one ring of the polycyclic aromatic group is an aromatic ring, the remaining rings may be either saturated alicyclic or unsaturated alicyclic. The aromatic group includes aromatic hydrocarbon groups and aromatic heterocyclic groups. Specific examples thereof include divalent aromatic hydrocarbon groups such as a phenylene group, a naphthylene group, anthranylene group, a phenanthrylene group, an azulenylene group, a pyrenylene group, a chrysenylene group, a fluorenylene group, a fluoranthenylene group, an indenylene group, an indanylene group, and a tetralinylene group; divalent 5-membered aromatic heterocyclic groups such as a pyrrolylene group, a furylene group, a thienylene group, an imidazolene group, a pyrazolene group, an oxazolene group, an isoxazolene group, a thiazolene group, an isothiazolene group, an indonylene group, an isoindolinylene group, an indolizinylene group, a benzimidazolene group, or a carbazolene group; Examples thereof include divalent 6-membered aromatic heterocyclic groups such as a pyridylene group, a pyrazinylene group, a pyrimidylene group, a pyridazylene group, a triazylene group, a quinolylene group, an isoquinolylene group, a quinoxalylene group, a cinolylene group, a quinazolylene group, a phthalazylene group, an acridylene group, a naphthazylene group, and a phenazylene group. Furthermore, the polycyclic aromatic group includes not only the above-mentioned groups in which aromatic rings are fused to each other, but also groups in which aromatic rings are directly bonded to each other, such as a biphenylene group. Preferably, an aromatic hydrocarbon group is used, more preferably a phenylene group, a naphthylene group or a biphenylene group, and particularly preferably a phenylene group.

[0014] The substituents on the divalent aromatic group are not particularly limited as long as they have the effect of the present invention. Specific examples of groups that can be "substituents" include the following groups.

[0015] C1-6 alkyl groups such as methyl and ethyl groups; C2-6 alkenyl groups such as vinyl groups and 1-propenyl groups; C2-6 alkynyl groups such as ethynyl and 1-propynyl groups; C3-8 cycloalkyl groups such as cyclopropyl and cyclobutyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; halogeno groups such as fluoro, chloro, bromo, and iodo groups; Examples of C1-6 haloalkyl groups include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group.

[0016] C in formula (I) m F 2m+1 (CH2) p and C n F 2n+1 (CH2) q In the formula (I), m and n each independently represent an integer of 1 to 20, and p and q each independently represent an integer of 0 to 6. m and n are preferably 4 or more.

[0017] C m F 2m+1 (CH2) p and C n F 2n+1 (CH2) qSpecific examples of the group represented by the formula (I) include a perfluoromethyl group, a perfluoroethyl group, a perfluoro-n-propyl group, a perfluoro-n-butyl group, a 1H,1H-perfluoro-n-butyl group, a perfluoro-n-pentyl group, a perfluoro-n-hexyl group, a 1H,1H,-perfluoro-n-pentyl group, a 1H,1H,2H,2H-perfluoro-n-hexyl group, a 1H,1H, Examples thereof include a 2H,2H,3H,3H-perfluoro-n-heptyl group, a 1H,1H,2H,2H-perfluoro-n-octyl group, a 1H,1H,2H,2H-perfluoro-n-nonyl group, a 1H,1H,2H,2H,3H,3H-perfluoro-n-nonyl group, a 1H,1H,2H,2H-perfluoro-n-decyl group, and a 1H,1H,2H,2H,3H,3H-perfluoro-n-dodecyl group.

[0018] As the aromatic ester compound represented by formula (1), Ar 1 and Ar 2 When is an aromatic hydrocarbon group, examples of the compounds include the following compounds. In Table 1, the symbols represent the following: Ph: 1,4-phenylene group, BiPh: 4,4'-biphenylene group, NaPh: 2,6-naphthylene group

[0019] [Table 1]

[0020] (Method for producing aromatic ester compound represented by formula (1)) The method for producing the aromatic ester compound represented by formula (1) is not particularly limited, but it can be synthesized, for example, by the following scheme or a scheme similar thereto.

[0021] (Process 1) [ka]

[0022] (Process 2) [ka] (Step 3)

[0023] [ka]

[0024] In the above reaction formula, Ar, a, b, m, n, p, and q are defined as in formula (1). R represents an alkyl group such as a methyl group or an ethyl group, and X represents a halogeno group such as an iodine atom.

[0025] In step 1, first, a thiol group-containing aromatic carboxylic acid compound (2) is reacted with an alcohol such as methanol in the presence of an acid catalyst such as sulfuric acid to obtain an ester compound (3). Next, the ester compound (3) is subjected to a C NMR spectroscopy in a solvent such as a ketone solvent, e.g., acetone, 2-butanone, 3-pentanone, or cyclohexanone, in the presence of an alkali metal compound such as KCO. m F 2m+1 (CH2) p After reacting with a fluoroalkyl halide represented by X to form a thioether, the ester group is hydrolyzed in the presence of an alkali metal hydroxide such as sodium hydroxide in a solvent such as an alcoholic solvent such as methanol or ethanol to form C m F 2m+1 (CH2) p An S group-containing aromatic carboxylic acid compound (4-1) is obtained. Further, the compound is oxidized with an oxidizing agent such as m-chloroperbenzoic acid or hydrogen peroxide to give the sulfinyl compound (4-2) or sulfonyl compound (4-3).

[0026] In step 2, the thiol group-containing aromatic alcohol compound (5) is reacted with C in a solvent such as a ketone solvent, for example, acetone, 2-butanone, 3-pentanone, or cyclohexanone, in the presence of an alkali metal compound, for example, KCO. n F 2n+1 (CH2) qand reacting with a fluoroalkyl halide represented by X to form C n F 2n+1 (CH2) q An S group-containing aromatic alcohol compound (6-1) is obtained. Further, the compound is oxidized with an oxidizing agent such as m-chloroperbenzoic acid or hydrogen peroxide to give the sulfinyl compound (6-2) or sulfonyl compound (6-3).

[0027] In step 3, the C obtained in step 1 is m F 2m+1 (CH2) p The S group-containing aromatic carboxylic acid compound (4-1), the sulfinyl compound (4-2), or the sulfonyl compound (4-3) (collectively referred to as compound (4)) is first converted into an acid halide using a halogenating agent such as thionyl chloride, and then the C obtained in step 2 is n F 2n+1 (CH2) q The target compound, aromatic ester compound (1) having both ends substituted with sulfur-containing fluoroalkane, is obtained by reacting with an S group-containing aromatic alcohol compound (6-1), a sulfinyl compound (6-2) or a sulfonyl compound (6-3) (collectively referred to as compound (6)) to effect esterification.

[0028] (Gelling agents or thickeners and gel compositions) The compound represented by formula (1) of the present invention can be used as a gelling agent or thickener to gel organic solvents or silicone oils. The compound of the present invention is advantageous in that it can gel or solidify a variety of organic solvents and silicone oils with the addition of a small amount. In addition, the gel composition of the present invention contains one or more compounds represented by formula (1) and an organic solvent or silicone oil. The gel composition of the present invention also includes gel electrolytes used as electrolytes for lithium ion secondary batteries and fuel cells.

[0029] (organic solvent) The organic solvent contained in the gel composition of the present invention is not particularly limited as long as it is an organic solvent. Preferred examples of the organic solvent include organic solvents that are liquid at room temperature.

[0030] Examples of such organic solvents include: Alcohols such as methanol, ethanol, isopropanol, butanol, and octanol; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, γ-butyrolactone, γ-valerolactone, and ε-caprolactone; Ketones such as acetone, diethyl ketone, methyl ethyl ketone, 3-pentanone; Hydrocarbons which may have a fluorine atom, such as pentane, hexane, octane, cyclohexane, perfluorodecalin, benzene, toluene, xylene, fluorobenzene, and hexafluorobenzene; Diethyl ether, 1,2-dimethoxyethane, 1,4-dioxane, crown ethers; Glymes; ethers such as tetrahydrofuran and fluoroalkyl ethers; amides such as N,N-dimethylacetamide, N,N-dimethylformamide, and N,N-diethylformamide; amines which may have a fluorine atom, such as ethylenediamine, N,N-diethylaniline, pyridine, and perfluorotributylamine; Carbonates such as propylene carbonate, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, diethyl carbonate, and ethyl methyl carbonate; nitriles such as acetonitrile, propionitrile, adiponitrile, and methoxyacetonitrile; lactams such as N -methylpyrrolidone ( NMP ); sulfones such as sulfolane; Sulfoxides such as dimethyl sulfoxide; Examples include silicon oil, industrial oils such as petroleum oil, and edible oil.

[0031] Ionic liquids can also be used as organic solvents. Ionic liquids refer to molten salts, and more specifically, refer to ionic salts that become liquid at around room temperature. Ionic liquids are liquids composed only of ions, and the cations that make up the ionic liquid are not limited to specific cations. Examples of such cations include those with nitrogen as the ion center, those with phosphorus as the ion center, those with sulfur as the ion center, and those with nitrogen and sulfur as the ion centers.

[0032] Examples of the cation having nitrogen as the ionic center include imidazolium cation, ammonium cation, pyridinium cation, quinolinium cation, pyrrolidinium cation, piperazinium cation, piperazinium cation, morpholinium cation, pyridazinium cation, pyrimidinium cation, pyrazinium cation, pyrazolium cation, thiazolium cation, oxazolium cation, triazolium cation, guanidium cation, 4-aza-1-azonia-bicyclo-[2,2,2]octanium, and the like. These cations may have a substituent, typically an alkyl group, at any position, and the number of substituents may be multiple.

[0033] Examples of imidazolium cations include 1,2,3-trialkylimidazolium such as 1-methylimidazolium, 1-ethylimidazolium, 1-propylimidazolium, 1-butylimidazolium, 1-butyl-3-methylimidazolium [BMIM], 1-ethyl-3-methylimidazolium [EMIM], 1-allyl-3-methylimidazolium, 1,3-diallylimidazolium, 1-benzyl-3-methylimidazolium, 1-methyl-3-octylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1-butyl-2,3-dimethylimidazolium, and 1,2-dimethyl-3-propylimidazolium; and 1-cyanopropyl- Examples include 3-methylimidazolium, 1,3-biscyanomethylimidazolium, 1,3-bis(3-cyanopropyl)imidazolium, 1-(2-hydroxyethyl)-3-methylimidazolium, 1-methoxyethyl-3-methylimidazolium, 1-[2-(2-methoxyethoxy)-ethyl]-3-methylimidazolium, 1,3-diethoxyimidazolium, 1,3-dimethoxyimidazolium, 1,3-dihydroxyimidazolium, 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylimidazolium, and 1-methyl-3-[(triethoxysilyl)propyl]imidazolium.

[0034] Examples of ammonium cations include tetramethylammonium, tetraethylammonium, tetrabutylammonium, diethylmethylammonium [dema], tetrahexylammonium, trihexyltetradecylammonium, (2-hydroxyethyl)trimethylammonium, N,N-diethyl-N-(2-methoxyethyl)-N-methylammonium [DEME], tris(2-hydroxyethyl)methylammonium, N,N-trimethyl-N-propylammonium [TMPA], trimethyl(1H,1H,2H,2H-heptadecafluorodecyl)ammonium, trimethyl-(4-vinylbenzyl)ammonium, tributyl-(4-vinylbenzyl)ammonium, 2-(methacryloyloxy)ethyltrimethylammonium, benzyldimethyl(octyl)ammonium, and N,N-dimethyl-N-(2-phenoxyethyl)-1-dodecylammonium.

[0035] Examples of the pyridinium cation include 1-ethylpyridinium, 1-butylpyridinium, 1-(3-hydroxypropyl)pyridinium, 1-ethyl-3-methylpyridinium, 1-butyl-3-methylpyridinium, 1-butyl-4-methylpyridinium, and 1-(3-cyanopropyl)pyridinium.

[0036] Examples of pyrrolidinium cations include 1-methyl-1-propylpyrrolidinium [P13], 1-butyl-1-methylpyrrolidinium, 1-(2-hydroxyethyl)-1-methylpyrrolidinium, and 1-ethyl-1-methylpyrrolidinium.

[0037] Examples of the piperidinium cation include 1-methyl-1-propylpiperidinium, 1-butyl-1-methylpiperidinium, 1-(2-hydroxyethyl)-1-methylpiperidinium, and 1-ethyl-1-methylpiperidinium.

[0038] Cations having phosphorus as the ionic center are generally called phosphonium cations, and specific examples thereof include tetrabutylphosphonium, tetrahexylphosphonium, trihexyltetradecylphosphonium, triphenylmethylphosphonium, (2-cyanoethyl)triethylphosphonium, (3-chloropropyl)trioctylphosphonium, tributyl(4-vinylbenzyl)phosphonium, triisobutylmethylphosphonium, triethylmethylphosphonium, tributylmethylphosphonium, tributylhexadecylphosphonium, and 3-(triphenylphosphonio)propane-1-sulfonic acid.

[0039] Cations with sulfur as the ionic center are generally called sulfonium cations, and specific examples include triethylsulfonium, tributylsulfonium, 1-ethyltetrahydrothiophenium, and 1-butyltetrahydrothiophenium.

[0040] The counter anions of the cations include fluoride, chloride, bromide, iodide, dicyanamide, bis(fluorosulfonyl)amide [FSA], bis(trifluoromethylsulfonyl)amide [TFSA], bis(trifluoroethylsulfonyl)amide, bis(pentafluoroethylsulfonyl)amide, bis(nonafluorobutylsulfonyl)amide, tetrafluoroborate [BF4], bis (trifluoromethyl)difluoroborate, (trifluoromethyl)trifluoroborate, tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, methanesulfonate, butylsulfonate, trifluoromethanesulfonate, tetrafluoroethanesulfonate, nonafluorobutanesulfonate, benzenesulfonate, p-toluenesulfonate, 2,4,6-trimethylbenzenesulfonate, styrenesulfonate, perfluorooctane sulfonate, heptadecafluorooctane sulfonate, 3-sulfopropyl methacrylate, 3-sulfopropyl acrylate, methyl sulfate, ethyl sulfate, octyl sulfate, diethylene glycol monomethyl ether sulfate, hydrogen sulfate, hexafluorophosphate [PF6], tris(trifluoromethyl)trifluorophosphate, tris(pentafluoroethyl)trifluorophosphate, dihydrogen phosphate, dibutyl phosphate, diethyl phosphate, dimethyl phosphate, bis(2,4,4-trimethylpentyl)phosphinate, methylphosphonate, methylmethylphosphonate, formate, acetate, propionate, butyrate, trifluoroacetate, hydroxyacetate, perfluorononanoate, decanoate, mandelate, thiosalicylate, benzoate, salicylate, fluorohydrogenate, lactate, glycinate, alaninate, leucinate, valinate, trifluoromethanesulfonyl leuc ... Examples of suitable fluoromethanesulfonyl valinate include nitrate, perchlorate, phenoxide, thiocyanate, tris(trifluoromethanesulfonyl)methide, acesulfamate, saccharinate, pyrazolate, imidazolate, thiazolate, triazolate, tetrazolate, indazolate, benzothiazolate, hexafluoroastatinate, hexafluoroantimonate, thiocyanate, tetrachloroaluminate, tetrachloroferrate [FeCl4], carbonate, methyl carbonate, and carbamate. These ionic liquids may be used singly or in combination of two or more.

[0041] Ionic liquids are classified into protic ionic liquids and aprotic ionic liquids. Protic ionic liquids are ionic liquids formed from an acid and a base, in which a proton transfers from the acid to the base to form a conjugate base and a conjugate acid. Aprotic ionic liquids are those that are not classified as protic ionic liquids. Examples of aprotic ionic liquids include [BMIM][TFSA] (1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide), [EMIM][FSA] (1-ethyl-3-methylimidazolium bis(fluorosulfonyl)amide), and the like. Examples of protic ionic liquids include protic ionic liquids such as [dema][TfO] (diethylmethylammonium trifluoromethanesulfonate) and [dema][TFSA] (diethylmethylammonium bis(trifluoromethylsulfonyl)amide), as well as hydrophobic protic ionic liquids such as [2,4-Lut][TFSA] and [N,N-MeAN][TFSA].

[0042] (gel electrolyte) The gelling agent of the present invention can gel high-dielectric-constant solvents suitable for organic electrolytes, such as dimethyl sulfoxide and propylene carbonate. The gel produced by gelling a high-dielectric-constant solvent with the gelling agent of the present invention can be used as a gel electrolyte. This gel electrolyte can be used in lithium-ion batteries. It can also be used as a gel electrolyte in dye-sensitized solar cells, fuel cells, and the like. The electrolyte is a common non-aqueous electrolyte used in electrolytic solutions, but when used in lithium ion secondary batteries, a lithium salt is used as a supporting electrolyte. Specific examples of lithium salts include, but are not limited to, LiPF6, LiBF4, LiClO4, LiAsF6, Li2SF6, and LiiOSO2C. k F 2k+1 (k is an integer from 1 to 8), LiN(SO2C k F 2k+1 )2 (k is an integer from 1 to 8), LiPF n (C k F 2k+1 ) 6-n [n is an integer from 1 to 5, k is an integer from 1 to 8], LiBF n (C k F 2k+1 ) 4-n [n is an integer of 1 to 3, and k is an integer of 1 to 8], lithium bis(oxalate)borate represented by LiB(C2O4)2, lithium difluoro(oxalate)borate represented by LiBF2(C2O4), lithium tetrafluoro(oxalate)phosphate represented by LiPF4(C2O4), LiPO2F2, and Li2PO3F. These lithium salts may be used singly or in combination of two or more.

[0043] (silicone oil) Examples of silicone oils include straight silicone oils, modified silicone oils such as reactive silicone oils and non-reactive silicone oils, and mixtures thereof. Examples of straight silicone oils include dimethyl silicone oil, methyl hydrogen silicone oil, methyl phenyl silicone oil, and cyclic dimethyl silicone oil. Examples of reactive silicone oils include those with both end groups (amino-modified, epoxy-modified, carbinol-modified, methacryl-modified, polyether-modified, mercapto-modified, carboxyl-modified, silanol-modified, acrylic-modified, carboxylic anhydride-modified, etc.), those with side chains (amino-modified, epoxy-modified, carbinol-modified, mercapto-modified, carboxyl-modified, methylhydrogen-modified, etc.), those with one end group (epoxy-modified, carbinol-modified, diol-modified, methacryl-modified, carboxyl-modified, etc.), and those with both side chain ends (side chain amino / both end methoxy-modified, epoxy-modified, etc.). Examples of non-reactive silicone oils include side-chain type (polyether-modified, aralkyl-modified, fluoroalkyl-modified, long-chain alkyl-modified, higher fatty acid ester-modified, higher fatty acid amide-modified, phenyl-modified, etc.) and both-end type (polyether-modified, etc.) non-reactive silicone oils.

[0044] (Preparation of gel composition) The gel composition of the present invention preferably contains 0.05 to 10.0% by mass, more preferably 0.1 to 8.0% by mass, and even more preferably 0.3 to 5.0% by mass of the compound represented by Formula (1) relative to its total weight. When this content is equal to or greater than the lower limit, the compound represented by Formula (1) tends to function more effectively as a gelling agent or thickener. When the content is equal to or less than the upper limit, economic efficiency and ease of handling tend to be further improved, and the gelling agent or thickener is further prevented from becoming an impurity, further preventing a decrease in the performance of the organic solvent. From the same perspective, the gel composition of the present invention preferably contains 90 to 99.95% by mass, more preferably 92 to 99.9% by mass, and even more preferably 95 to 99.7% by mass of the organic solvent or silicone oil relative to its total weight.

[0045] The gel composition of the present invention may contain, in addition to the compound represented by formula (1) and the organic solvent or silicone oil, other components within the range that do not inhibit the function of the compound represented by formula (1) as a gelling agent or thickening agent. Such components include, for example, gelling agents other than the compound represented by formula (1), coagulants, thickening agents, stabilizers, antioxidants, emulsifiers, lubricants, and safety-improving additives.

[0046] The method for preparing the gel composition of the present invention is not particularly limited, but it can be prepared, for example, by mixing an organic solvent or silicone oil, a compound represented by formula (1), and other additives while heating to form a uniform mixture, and then cooling the mixture. The order in which the components are mixed is not particularly important, but it is preferable to prepare a solution consisting of an organic solvent or silicone oil and additives in advance and then mix the compound represented by formula (1), as this makes it easier to form a uniform mixture. [Example]

[0047] The present invention will be described in more detail below with reference to examples, but the technical scope of the present invention is not limited to these examples. Not limited.

[0048] measuring equipment Melting point (mp): Measured using a micro melting point analyzer (RFS-10 special model) manufactured by J-Science Co., Ltd. Nuclear magnetic resonance (NMR) spectra were measured using a JEOL JMN-LA500 (500 MHz) spectrometer. The solvents used were CDCl3 (internal standard CH3 in tetramethylsilane (TMS, (CH3)4Si) = 0 ppm) or DMSO-d6 (internal standard CH3 in DMSO = 2.49 ppm). Data were analyzed using JEOL Delta NMR software (Delta 5.0). Infrared absorption (IR) spectrum: Measurements were made using an IRPrestige-21 manufactured by Shimadzu Corporation. Measurements were made using potassium bromide discs (KBr discs) or attenuated total refraction (ATR) using a Quest manufactured by Specac Ltd. Analysis was performed using LabSolutions IR manufactured by Shimadzu Corporation.

[0049] [Synthesis example] Sixteen compounds of the present invention were synthesized according to the following steps. (1) Esterification of 4-mercaptobenzoic acid (synthesis of compound A) [ka] A 1 L recovery flask was charged with 24.9 g (161 mmol) of 4-mercaptobenzoic acid, 400 mL of methanol, and 12 mL of concentrated sulfuric acid, and refluxed for 3 days. After the reaction was complete, the mixture was allowed to cool to room temperature. The reaction mixture was transferred to a 1 L separatory funnel, and 200 mL of cyclopentyl methyl ether and 150 mL of water were added. The organic phase was washed with water. The resulting organic phase was further washed with 150 mL of saturated brine. 20 g of anhydrous magnesium sulfate was added to the resulting organic phase, and the mixture was allowed to stand for 1 hour to dehydrate. The anhydrous magnesium sulfate was then filtered off, and the organic phase was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from methanol to give compound A as a colorless powder in 98% yield (26.2 g, 158 mmol). mp = 50 - 51℃, ATR-IR: ν C=O = 1716 cm -1 , ν C-H = 2900-2449 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 3.54 (1H, s), 3.82 (4H, d, J=3.4 Hz), 7.21 (2H, d, J=8.0 Hz), 7.81 (2H, d, J=8.0 Hz) ppm

[0050] (2) Thioetherification of mercapto groups 1) Synthesis of Compound B-4 [ka] Compound A (14.4 g, 85.7 mmol), 300 mL of 2-butanone, potassium carbonate (11.0 g, 79.7 mmol), and 2-(perfluorobutyl)ethyl iodide (32.56 g, 87.1 mmol) were added to a 500 mL recovery flask and refluxed for 2 days. After the reaction was complete, the mixture was allowed to cool to room temperature and the solid was filtered off. The filtrate was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from methanol to give compound B-4 as a yellow powder in a 93% yield (33.1 g, 79.9 mmol). mp = 43-44℃, ATR-IR: ν C-F= 1132 - 1355 cm -1 , ν C=O = 1716 cm -1 , ν C-H = 2950 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.32-2.45 (2H, m), 3.13-3.16 (2H, m), 3.85 (3H, s), 7.26 (2H, d, J=8.6 Hz), 7.91 (2H, d, J=8.6 Hz) ppm

[0051] 2) Synthesis of Compound B-6 [ka] Compound A (11.3 g, 66.9 mmol), 2-(perfluorohexyl)ethyl iodide (31.8 g, 67.0 mmol), potassium carbonate (8.56 g), and 300 mL of 3-pentanone were added to a 500 mL recovery flask and refluxed for 2 days. After the reaction was complete, the mixture was allowed to cool to room temperature and the solid was filtered off. The filtrate was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from methanol to give compound B-6 as a yellow solid in a 90% yield (31.0 g, 60.3 mmol). mp = 68-70℃, ATR-IR: ν C-F = 1139-1365 cm -1 , ν C=O = 1716 cm -1 , ν C-H = 2958 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 0.99 (1H, t, J=7.4 Hz), 2.32-2.42 (2H, m), 3.12-3.15 (2H, m), 3.84 (2H, s), 7.26 (2H, d, J=8.0 Hz), 7.91 (2H, d, J=8.6 Hz) ppm

[0052] (3) Hydrolysis of esters 1) Synthesis of Compound C-4 [ka] Compound B-4 (15.0 g, 36.2 mmol), 80 mL of 10N NaOH, and 400 mL of methanol were added to a 1 L recovery flask and refluxed for 2 hours. After the reaction was complete, the mixture was allowed to cool to room temperature. The reaction mixture was transferred to a 2 L Erlenmeyer flask, cooled thoroughly in an ice bath, and then 70 mL of 12N HCl was added and stirred under acidic conditions for 1 hour. The resulting solid was filtered with suction and washed with acetone to give compound C-4 as a colorless powder in a 32% yield (4.69 g, 11.7 mmol). mp = 140-141℃, ATR-IR: ν C-F = 1130-1354 cm -1 , ν C=O = 1716 cm -1 , ν O-H = 2561-3070 cm -1 , 1 H-NMR (500 MHz, DMSO-d6): δ = 2.56-2.65 (5H, m), 7.45 (2H, d, J=8.6 Hz), 7.90 (2H, d, J=8.6 Hz) ppm

[0053] 2) Synthesis of Compound C-6 [ka] Compound B-6 (30.8 g, 59.9 mmol), 120 mL of 10N NaOH, and 500 mL of methanol were added to a 1 L recovery flask and refluxed for 2 hours. After the reaction was complete, the mixture was allowed to cool to room temperature. The reaction mixture was transferred to a 2 L Erlenmeyer flask, cooled thoroughly in an ice bath, and then 150 mL of 12N HCl and 85 g of ice were added and stirred under acidic conditions for 1 hour. The resulting solid was filtered with suction and washed with acetone to give compound C-6 as a colorless powder in 76% yield (22.8 g, 45.6 mmol). ATR-IR: ν C-F = 1139-1365 cm -1 , ν C=O = 1680 cm -1 , ν O-H= 2547-2997 cm -1 , 1 H NMR (500MHz, DMSO-d6): δ = 2.56 (2H, m), 3.34 (2H, m), 7.45 (2H, d, J=8.5 Hz), 7.81 (2H, d, J=8.0 Hz), 12.96 (1H, s) ppm

[0054] (4) Sulfonylation 1) Synthesis of Compound D-4 [ka] Compound C-4 (1.00 g, 2.50 mmol) was placed in a 200 mL recovery flask and dissolved in 100 mL of chloroform. Next, m-chloroperbenzoic acid (1.50 g, 8.69 mmol) and 60 mL of chloroform were added to a 100 mL beaker to completely dissolve the m-chloroperbenzoic acid. This mixture was then added to a 200 mL recovery flask and refluxed for 2 days. After the reaction was complete, the reaction mixture was transferred to a separatory funnel, and 50 mL of 0.1 M aqueous sodium bisulfite and 50 mL of 0.1 M aqueous sodium bicarbonate were added to wash the organic phase. The resulting organic phase was washed again with saturated brine and dehydrated over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from toluene to give compound D-4 in 84% yield (0.91 g, 2.11 mmol). mp = 159-161℃, ATR-IR: ν C-F = 1130-1350 cm -1 , ν C-O = 1705 cm -1 , ν O-H = 2540-2970 cm -1 , 1 H-NMR (500 MHz, DMSO-d6): δ = 2.47 (2H, d, J=1.7 Hz), 3.66 (2H, t, J=7.4 Hz), 7.88 (2H, d, J=6.9 Hz), 8.05 (2H, d, J=6.9 Hz) ppm

[0055] 2) Synthesis of Compound D-6 [ka] Compound C-6 (10.0 g, 19.9 mmol), 30 wt% H2O2 (11.4 g, 101 mmol), and 200 mL of acetic acid were added to a 300 mL recovery flask and refluxed for 3 days. After the reaction was complete, the mixture was allowed to cool to room temperature, and 60 mL of 20 wt% aqueous sodium sulfite solution was added to the reaction solution and washed with water. The precipitate was filtered under suction to obtain compound D-6 as a colorless solid in 99% yield (10.6 g, 19.9 mmol). mp = 268-269℃, IR (KBr disc.): ν C-F = 1040-1280 cm -1 , ν S=O = 1120-1363 cm -1 , ν C-O = 1283 cm -1 , ν C=C = 1600 cm -1 , ν C=O = 1720 cm -1 , ν C-H = 2950 cm -1 , ν O-H = 3440 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.48-2.73 (2H, m), 3.34 (2H, s), 8.03 (2H, d, J=8.6 Hz), 8.28 (2H, d, J=8.6 Hz) ppm

[0056] (5) Thioetherification of 4-mercaptophenol 1) Synthesis of compound E-4 [ka] A 500 mL recovery flask was charged with 4-mercaptophenol (8.78 g, 69.6 mmol), 2-(perfluorobutyl)ethyl iodide (26.7 g, 71.4 mmol), potassium carbonate (9.57 g), and 200 mL of 2-butanone, and the mixture was refluxed for 3 days. After the reaction was complete, the reaction mixture was transferred to a separatory funnel, and the organic phase was washed with ethyl acetate, 1 M HCl, and saturated brine. The resulting organic phase was dried over anhydrous magnesium sulfate for 30 minutes. The solid was filtered off, and the filtrate was concentrated under reduced pressure using an evaporator. The resulting product was purified by silica gel chromatography (eluent: chloroform) to give compound E-4 as a colorless powder in a 45% yield (4.75 g, 12.8 mmol). mp = 54-56℃, ATR-IR: ν C-F = 1128-1356 cm -1 , ν O-H = 3587-3649 cm -1 , ν C-H = 2966 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.21-2.31 (2H, m), 2.91-2.94 (2H, m), 6.75 (2H, d, J=8.6 Hz), 7.27 (2H, d, J=8.6 Hz) ppm

[0057] 2) Synthesis of compound E-6 [ka] A 300 mL recovery flask was charged with 4-mercaptophenol (5.77 g, 45.7 mmol), 2-(perfluorohexyl)ethyl iodide (21.7 g, 45.8 mmol), potassium carbonate (6.40 g), and 3-pentanone (120 mL) and refluxed for 3 days. After the reaction was complete, the reaction mixture was transferred to a separatory funnel, and the organic phase was washed with ethyl acetate, 1 M HCl, and saturated brine. The resulting organic phase was dried over anhydrous magnesium sulfate for 30 minutes. The solid was filtered off, and the filtrate was concentrated under reduced pressure using an evaporator. The resulting product was purified by silica gel chromatography (eluent: chloroform) to obtain compound E-6 as a colorless powder in a 96% yield (19.4 g, 41.0 mmol). mp = 70-71℃, ATR-IR: ν C-F = 1128-1356 cm -1 , ν O-H = 3587-3649 cm -1 , ν C-H = 2966 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ= 2.20-2.31 (2H, m), 2.89-2.92 (2H, m), 6.76 (2H, d, J=8.6 Hz), 7.25 (2H, d, J=8.6 Hz) ppm

[0058] (6) Sulfonylation 1) Synthesis of compound F-4 [ka] Compound E-4 (1.00 g, 2.69 mmol) was placed in a 200 mL recovery flask and dissolved in 100 mL of chloroform. Next, m-chloroperbenzoic acid (1.50 g, 8.69 mmol) and 60 mL of chloroform were added to a 100 mL beaker to completely dissolve the m-chloroperbenzoic acid. This mixture was then added to a 200 mL recovery flask and refluxed for 2 days. After the reaction was complete, the reaction mixture was transferred to a separatory funnel, and 50 mL of 0.1 M aqueous sodium bisulfite and 50 mL of 0.1 M aqueous sodium bicarbonate were added to wash the organic phase. The resulting organic phase was washed again with saturated brine and dehydrated over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from toluene to give compound F-4 as a colorless powder in 84% yield (0.91 g, 2.25 mmol). mp = 98-100℃, ATR-IR: ν C-F = 1128-1356 cm -1 , ν O-H = 3220-3420 cm -1 , ν S=O = 1330cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.53-2.63 (2H, m), 3.30-3.34 (2H, m), 7.02 (2H, d, J=8.6 Hz), 7.80 (2H, d, J=9.2 Hz) ppm

[0059] 2) Synthesis of compound F-6 [ka] Compound E-6 (10.0 g, 21.2 mmol), 15 g of 35 wt% HO, and 200 mL of acetic acid were added to a 200 mL recovery flask and refluxed for 3 days. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from toluene to give compound F-6 as a colorless powder in an 86% yield (9.19 g, 18.2 mmol). mp = 98-100℃, ATR-IR: ν C-F= 1128-1356 cm -1 , ν O-H = 3220-3420 cm -1 , ν S=O = 1330cm -1 , 1 H-NMR (500 MHz, DMSO-d6): δ = 2.46-2.47 (2H, m), 3.50-3.54 (2H, m), 6.94 (2H, d, J=8.6 Hz), 7.73 (2H, d, J=9.2 Hz) ppm

[0060] (7) Synthesis of target compound 1) Compounds with fluoroalkylthio groups at both ends 1-1) Synthesis of Compound 1-4-4 [ka] Compound C-4 (0.50 g, 1.25 mmol) and 8 mL of thionyl chloride were added to a 50 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 8 mL of toluene and 8 mL of a pyridine solution of compound E-4 (0.55 g, 1.48 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 1-4-4 as a colorless powder in a 50% yield (0.47 g, 0.62 mmol). mp = 117-119℃, ATR-IR: ν C-F = 1130-1354 cm -1 , ν C=O =1728 cm -1 , 1H-NMR (500 MHz, CDCl3): δ = 2.30-2.46 (4H, m), 3.04-3.08 (2H, m), 3.17-3.21 (2H, m), 7.14 (2H, d, J=8.6 Hz), 7.33 (2H, d, J=8.6 Hz), 7.38 (2H, d, J=9.2 Hz), 8.07 (2H, d, J= 8.6 Hz) ppm

[0061] 1-2) Synthesis of Compound 1-4-6 [ka] C-4 (1.40 g, 3.49 mmol) and 8 mL of thionyl chloride were added to a 50 mL recovery flask, a calcium chloride tube was attached, and the mixture was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath, and 8 mL of toluene and 8 mL of a pyridine solution of compound E-6 (1.80 g, 3.81 mmol) were added. A calcium chloride tube was attached, and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 1-4-6 as a colorless powder in an 82% yield (2.44 g, 2.85 mmol). mp = 120-122℃, ATR-IR: ν C-F = 1132-1354 cm -1 , ν C=O = 1726 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.29-2.46 (4H, m), 3.05 (2H, t, J = 8.0 Hz), 3.18 (2H, t, J=8.3 Hz), 7.13 (2H, d, J=8.6 Hz), 7.32 (2H, d, J=8.6 Hz), 7.38 (2H, d, J=8.6 Hz), 8.06 (2H, d, J=8.0 Hz) ppm

[0062] 1-3) Synthesis of Compound 1-6-4 [ka] Compound C-6 (1.82 g, 3.64 mmol), 20 mL of thionyl chloride, and 30 mL of chloroform were added to a 100 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes with a calcium chloride tube attached. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 8 mL of toluene and 8 mL of a pyridine solution of compound E-4 (1.38 g, 3.70 mmol) were added, and the flask was stirred at 80 °C for 4 hours with a calcium chloride tube attached. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 1-6-4 as a colorless powder in a 43% yield (1.33 g, 1.56 mmol). mp = 119-120℃, ATR-IR: ν C-F = 1132-1355 cm -1 , ν C=O = 1728 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.36-2.53 (4H, m), 3.10-3.14 (2H, m), 3.23-3.26 (2H, m), 7.20 (2H, d, J=8.6 Hz), 7.39 (2H, d, J=8.6 Hz), 7.44 (2H, d, J=8.6 Hz), 8.13 (2H, d, J=8.6 Hz)ppm

[0063] 1-4) Synthesis of Compound 1-6-6 [ka] Compound C-6 (1.58 g, 3.15 mmol) and 20 mL of thionyl chloride were added to a 100 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 8 mL of toluene and 15 mL of a pyridine solution of compound E-6 (1.51 g, 3.20 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 1-6-6 as a colorless powder in a 53% yield (1.61 g, 1.69 mmol). mp = 134-135℃, ATR-IR: ν C-F = 1132-1354 cm -1 , ν C=O = 1726 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.35-2.52 (4H, m), 3.10-3.13 (2H, m), 3.23-3.26 (2H, m), 7.19 (2H, d, J=9.2 Hz), 7.38 (2H, d, J=10.9 Hz), 7.44 (2H, d, J=8.6 Hz), 8.12 (2H, d, J=8.6 Hz) ppm

[0064] 2) Compounds in which one end is a fluoroalkylthio group and the other end is a fluoroalkylsulfonyl group 2-1) Synthesis of Compound 2-4-4 [ka] Compound D-4 (0.40 g, 0.93 mmol) and 8 mL of thionyl chloride were added to a 50 mL recovery flask, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 8 mL of toluene and 8 mL of a pyridine solution of compound E-4 (0.41 g, 1.10 mmol) were added, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 2-4-4 in a 40% yield (0.29 g, 0.37 mmol). mp = 133-135℃, ATR-IR: ν C-F = 1130-1355 cm -1 , ν C=O =1720-1735 cm -1 , ν C-H = 2966 cm -1 , ν S=O = 1330 cm -1 , 1 H-NMR (500 MHz, CDCl3):δ = 2.23-2.41 (2H, m), 2.51-2.62 (2H, m), 3.07 (2H, t, J=5.3 Hz), 3.30-3.34 (2H, m), 7.16 (2H, d, J=6.9 Hz), 7.40 (2H, d, J=8.6 Hz), 8.04 (2H, d, J=8.6 Hz), 8.37 (2H, d, J=8.6 Hz) ppm

[0065] 2-2) Synthesis of Compound 2-4-6 [ka] Compound D-4 (0.30 g, 0.69 mmol) and 8 mL of thionyl chloride were added to a 50 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 8 mL of toluene and 8 mL of a pyridine solution of compound E-6 (0.40 g, 0.85 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 2-4-6 as a colorless powder in a 78% yield (0.48 g, 0.54 mmol). mp = 158-161℃, ATR-IR: ν C-F = 1132-1357 cm -1 , ν C=O = 1738 cm -1 , ν S=O = 1333 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.23-2.40 (2H, m), 2.51-2.61 (2H, m), 3.05-3.08 (2H, m), 3.30-3.33 (2H, m), 7.15 (2H, d, J=6.3 Hz), 7.39 (2H, d, J=8.6 Hz), 8.04 (2H, d, J=8.6 Hz), 8.36 (2H, d, J=8.6 Hz) ppm

[0066] 2-3) Synthesis of Compound 2-6-4 [ka] Compound D-6 (2.41 g, 4.52 mmol), 15 mL of thionyl chloride, and 15 mL of chloroform were added to a 100 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 20 mL of toluene and 10 mL of a pyridine solution of compound E-4 (1.68 g, 3.56 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 2-6-4 as a colorless powder in a 37% yield (1.50 g, 1.69 mmol). mp = 134-135℃, ATR-IR: ν C-F = 1132-1357 cm -1 , ν C=O = 1736 cm -1 , ν S=O = 1332 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.37-2.47 (2H, m), 2.58-2.68 (2H, m), 3.14 (2H, q, J=5.3 Hz), 3.37-3.40 (2H, m), 7.23 (2H, d, J=9.7 Hz), 7.46 (2H, d, J=9.2 Hz), 8.11 (2H, d, J=8.6 Hz), 8.43 (2H, d, J=8.6 Hz) ppm

[0067] 2-4) Synthesis of Compound 2-6-6 [ka] Compound D-6 (1.64 g, 3.08 mmol) and 25 mL of thionyl chloride were added to a 100 mL recovery flask, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 40 mL of toluene and 20 mL of a pyridine solution of compound E-6 (1.60 g, 3.37 mmol) were added, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 2-6-6 as a colorless powder in a 53% yield (1.60 g, 1.62 mmol). mp = 135-136℃, ATR-IR: ν C-F = 1139-1342 cm -1 , ν C=O =1735 cm -1 , ν S=O = 1321 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ= 2.29-2.46 (4H, m), 3.04-3.07 (2H, m), 3.17-3.20 (2H, m), 7.13 (2H, d, J=9.2 Hz), 7.32 (2H, d, J=8.6 Hz), 7.38 (2H, d, J=8.6 Hz), 8.06 (2H, d, J=8.6 Hz) ppm

[0068] 2-5) Synthesis of Compound 3-4-4 [ka] Compound C-4 (0.40 g, 1.00 mmol) and 8 mL of thionyl chloride were added to a 50 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 11 mL of toluene and 8 mL of a pyridine solution of compound F-4 (0.52 g, 1.36 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 3-4-4 as a colorless powder in a 51% yield (0.40 g, 0.51 mmol). mp = 170-173℃, ATR-IR: ν C-F = 1132-1357 cm -1 , ν C=O = 1732 cm -1 , ν C-H = 2966 cm -1 , ν S=O = 1323 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.36-2.63 (4H, m), 3.18-3.22 (2H, m), 3.28-3.31 (2H, m), 7.34 (2H, d, J=8.0 Hz), 7.43 (2H, d, J=6.9 Hz), 7.96 (2H, d, J=8.6 Hz), 8.07 (2H, d, J=8.6 Hz) ppm

[0069] 2-6) Synthesis of Compound 3-4-6 [ka] Compound C-4 (1.03 g, 2.57 mmol) and 10 mL of thionyl chloride were added to a 50 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 11 mL of toluene and 10 mL of a pyridine solution of compound F-6 (1.20 g, 2.38 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized from a chloroform-ethanol mixed solvent to give compound 3-4-6 as a colorless powder in a 13% yield (0.29 g, 0.33 mmol). mp = 178-180℃, ATR-IR: ν C-F = 1132-1357 cm -1 , ν C=O = 1732 cm -1 , ν C-H =2966 cm -1 , ν S=O = 1323 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.36-2.46 (2H, m), 2.52-2.62 (2H, m), 3.19 (2H, q, J=5.5 Hz), 3.27-3.30 (2H, m), 7.33 (2H, d, J=8.6 Hz), 7.42 (2H, d, J=8.6 Hz), 7.95 (2H, d, J=8.6 Hz), 8.06 (2H, d, J=8.6 Hz) ppm

[0070] 2-7) Synthesis of Compound 3-6-4 [ka] Compound C-6 (0.54 g, 1.08 mmol) and 20 mL of thionyl chloride were added to a 50 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 15 mL of toluene and 5 mL of a pyridine solution of compound F-4 (0.36 g, 0.89 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized twice from a chloroform-ethanol mixed solvent to give compound 3-6-4 as a colorless powder in an 88% yield (0.70 g, 0.78 mmol). mp = 174-175℃, ATR-IR: ν C-F = 1134-1359 cm -1 , ν C=O = 1732 cm -1 ,ν S=O = 1321 cm -1 , 1 H-NMR (500 MHz, CDCl3): δ = 2.43-2.54 (2H, m), 2.59-2.69 (2H, m), 3.27 (2H, q, J=5.3 Hz), 3.34-3.37 (2H, m), 7.40 (2H, d, J=8.6 Hz), 7.50 (2H, d, J=8.6 Hz), 8.02 (2H, d, J=6.3 Hz), 8.14 (2H, d, J=8.0 Hz)ppm

[0071] 2-8) Synthesis of Compound 3-6-6 [ka] Compound C-6 (1.53 g, 3.05 mmol) and 25 mL of thionyl chloride were added to a 100 mL recovery flask, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 10 mL of toluene and 10 mL of a pyridine solution of compound F-6 (1.54 g, 3.05 mmol) were added, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was recrystallized twice from a chloroform-ethanol mixed solvent to give compound 3-6-6 as a colorless powder in a 40% yield (1.20 g, 1.21 mmol). mp = 178-179℃, ATR-IR: ν C-F = 1139-1367 cm -1 , ν C=O = 1732 cm -1 , ν S=O = 1321 cm -1 , 1 H-NMR (500 MHz,CDCl3): δ = 2.42-2.53 (2H, m), 2.58-2.70 (2H, m), 3.19-3.27 (2H, m), 3.34-3.42 (2H, m), 7.40 (2H, d, J=8.6 Hz), 7.49 (2H, d, J=8.6 Hz), 8.02 (3H, d, J=8.6 Hz), 8.13 (2H, d, J=8.6 Hz)ppm

[0072] 3) Compounds with fluorosulfonyl groups at both ends 3-1) Synthesis of Compound 4-4-4 [ka] Compound D-4 (0.26 g, 0.60 mmol) and 10 mL of thionyl chloride were added to a 50 mL recovery flask, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 7 mL of toluene and 7 mL of a pyridine solution of compound F-4 (0.24 g, 0.60 mmol) were added, and a calcium chloride tube was attached and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was washed with chloroform and ethanol to give compound 4-4-4 as a colorless powder in a 58% yield (0.29 g, 0.35 mmol). mp > 300℃, ATR-IR: ν C-F = 1130-1355 cm -1 , ν C=O = 1737 cm -1 , ν C-H =2966 cm -1 , ν S=O = 1321 cm -1 , 1 H-NMR: Measurement was not possible because it was insoluble in both CDCl3 and DMSO-d6.

[0073] 3-2) Synthesis of Compound 4-4-6 [ka] Compound D-4 (0.51 g, 1.18 mmol) and 9 mL of thionyl chloride were added to a 50 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 9 mL of toluene and 10 mL of a pyridine solution of compound F-6 (0.72 g, 1.42 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was washed with chloroform and ethanol to give compound 4-4-6 as a colorless powder in a 42% yield (0.49 g, 0.53 mmol). mp = 249-251℃, ATR-IR: ν C-F = 1130-1355 cm -1 , νC=O = 1687 cm -1 , ν C-H =2966 cm -1 , ν S=O = 1321cm -1 , 1 H-NMR: Measurement was not possible because it was insoluble in both CDCl3 and DMSO-d6.

[0074] 3-3) Synthesis of Compound 4-6-4 [ka] Compound D-6 (1.16 g, 2.17 mmol), 15 mL of thionyl chloride, and 30 mL of chloroform were added to a 100 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 20 mL of toluene and 10 mL of a pyridine solution of compound F-4 (0.87 g, 2.15 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was washed with chloroform and ethanol to give compound 4-6-4 as a colorless powder in an 85% yield (1.69 g, 1.83 mmol). mp = 213-214℃, ATR-IR: ν C-F = 1130-1355 cm -1 , ν C=O = 1735 cm -1 , ν S=O = 1322 cm -1 , 1 H-NMR: Measurement was not possible because it was insoluble in both CDCl3 and DMSO-d6.

[0075] 3-4) Synthesis of Compound 4-6-6 [ka] Compound D-6 (1.75 g, 3.50 mmol), 15 mL of thionyl chloride, and 30 mL of chloroform were added to a 100 mL recovery flask, and the flask was stirred at 80 °C for 45 minutes. After the reaction was complete, the solvent was removed under reduced pressure in an 80 °C water bath. 30 mL of toluene and 105 mL of a pyridine solution of compound F-6 (1.70 g, 3.37 mmol) were added, and the flask was stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was concentrated under reduced pressure using an evaporator. The resulting product was washed with chloroform and ethanol to give compound 4-6-6 as a colorless powder in a 77% yield (2.76 g, 2.70 mmol). mp 241-242℃, ATR-IR: ν C-F = 1138-1357 cm -1 , ν C=O =1739 cm -1 , ν S=O = 1321 cm -1 , 1 H-NMR: Measurement was not possible because it was insoluble in both CDCl3 and DMSO-d6.

[0076] [Gelation ability (minimum gelation concentration, sol-gel transition temperature) measurement] Approximately 3.5 mg of gelling agent was weighed into a microtube (Maruem Co., Ltd., 11 mm diameter). The gelling agent was mixed with an appropriate amount of solvent and the resulting mixture was heated in the microtube to dissolve, then vigorously stirred using a vortex mixer. After cooling, the state of the solution was visually confirmed. When the sample tube was inverted, if it was in a solid state it was deemed a "gel," and if it was in a liquid state it was deemed a "sol." If it was determined to be a gel, further solvent was added to determine the minimum gelling concentration. The temperature at which the phase transition from the gel state to the sol state occurred was also measured, and this was designated the "sol-gel transition temperature." The minimum gelling concentrations are shown in Tables 2 to 5, and the sol-gel transition temperatures are shown in Figures 1 to 25. In the tables, G indicates that gelation occurred. "-" indicates that no gelation occurred or that the sample was insolubilized at a concentration of 5%. Note that G means gel and I means insoluble. The numbers in parentheses indicate the minimum gelling concentration (wt%). In addition, the numbers 1-4-4 to 4-6-6 at the top of the table indicate the numbers of the compounds synthesized in the above synthesis examples.

[0077] [Table 2]

[0078] [Table 3]

[0079] [Table 4]

[0080] [Table 5]

[0081] DEMNUM®: [ka] Krytox®: [ka] [DEME][TFSA]: [ka] [BMIM][TFSA]: [ka]

[0082] As described above, the compound of the present invention formed gels by heating, dissolving, and cooling even in small amounts of 5% or less in hydrocarbons such as n-octane and toluene, alcoholic solvents such as ethanol and 1-octanol, high-dielectric solvents (solvents that can serve as electrolytes) such as acetonitrile and propylene carbonate, and ionic liquids such as [DEME][TFSA] and [BMIM][TFSA]. Furthermore, gelation was also possible with silicone oils such as Poly(methylhydrosiloxane), Poly(dimethylsiloxane), and Poly(methylphenylsiloxane) even when added in amounts of 5% or less.

[0083] 1 to 4 show the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound of the present invention and 1-octanol. 5 to 8 show the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound of the present invention and propylene carbonate. 9 to 12 show the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compound of the present invention and [DEME][TFSA]. 13 to 16 show the relationship between the phase transition temperature to a sol and the compound concentration for gels of the compound of the present invention and [BMIM][TFSA]. 17 to 19 show the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound of the present invention and Poly(methylhydrosiloxane). 20 to 22 show the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound of the present invention and Poly(dimethylsiloxane). 23 to 25 show the relationship between the phase transition temperature to a sol and the compound concentration for a gel of the compound of the present invention and Poly(methylphenylsiloxane).

[0084] [Thickening effect and thixotropy] The rheological properties of silicone oil gels containing 5 wt% of compound 1-6-6 were measured using a Rheosol-G1000T manufactured by UBM Co., Ltd. under the following conditions. Poly(methylhydrosiloxane); PMHS showed a 100-fold increase in viscosity (Figure 26). Similarly, when the ionic liquid [BMIM][TFSA] gel containing 5 wt% of compound 1-6-6 was measured, the viscosity of [BMIM][TFSA] alone was 5.2 × 10 -2 Since the viscosity is in Pa·s, an increase of approximately 120,000 times was observed. This suggests that a thickening effect can be expected. <Measurement conditions> Measurement mode: Shear rate dependency: 2.76 x 10 -2 ~ 143 seconds -1 Chuck: Corn plate Cone diameter: 40 mm Cone angle: 2.0° Rotation speed: 0.01 to 50 ppm Temperature: 20℃ (room temperature) Furthermore, in the gel samples of commercially available representative hydrophobic ionic liquids [BMIM][TFSA] and PMHS, there was almost no change in viscosity before and after shearing, indicating that they were unique gels with thixotropy (Figures 26 and 27). [Industrial Applicability]

[0085] The fluorine-containing aromatic ester compound of the present invention can be used as a gelling agent or thickening agent in industrial fields such as cosmetics, pharmaceuticals, food, paints, adhesives, and sludge treatment, and can also be used to gel ionic liquids and silicone oils. Since silicone oil gel has thixotropy, it is thought that it can be used as a liquid when applied to a substrate and then retained as a gel again afterwards. Furthermore, it is predicted to have excellent electrochemical stability and will not decompose due to changes in pH. In addition, the ionic conductivity of the formed organic gel electrolyte is almost the same as that of the liquid state. This may enable the construction of next-generation organic gel electrolytes that combine high ionic conductivity with mechanical strength, and is expected to be applied to all-solid-state lithium-ion batteries and fuel cells. Furthermore, the ionic liquid gel produced by the gelling agent or thickener of the present invention selectively absorbs carbon dioxide and, because it is a hydrophobic ionic liquid gel, can easily be separated from water. Therefore, it is expected to be applied to carbon dioxide separation membranes, and it can be used as an innovative CO2 separation material that can remove acid gases and water with the ultimate goal of CO2 reuse.

Claims

1. An aromatic ester compound represented by formula (1): 【Chemistry 1】 (In the formula, Ar １ and Ar ２ each independently represents a substituted or unsubstituted divalent aromatic group, a and b each independently represent 0, 1, or 2; m and n each independently represent an integer of 1 to 20, p and q each independently represent an integer of 0 to 6.

2. Ar in formula (1) １ and Ar ２ 2. The aromatic ester compound according to claim 1, wherein is a substituted or unsubstituted phenylene group, naphthylene group, or biphenylene group.

3. A gelling agent or thickening agent containing the aromatic ester compound according to claim 1 or 2.

4. A gel composition comprising the gelling agent or thickener according to claim 3 and an organic solvent or silicone oil.

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