Amine detection method

Abstract

To provide an amine detection method capable of detecting the amine with high sensitivity and good reproducibility by having a large amount of fluorescence quantum change before and after contacting with the amine.SOLUTION: In a method for detecting an amine, the amine is detected from a difference between a maximum fluorescence intensity X1 of a fluorescent substance represented by formula 1 before contacting the amine and a maximum fluorescence intensity X2 of the fluorescent substance after contacting the fluorescent substance to the amine. In the formula 1, R represents a hydrogen atom, an alkyl group which may have a substituent, a benzyl group which may have a substituent, or an aryl group which may have a substituent, A represents a spacer, and Z represents an atomic group which exhibits fluorescence emission upon photoexcitation.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to a method for detecting amines using a fluorescent substance. [Background technology]

[0002] The detection of amines is important for monitoring air and environmental pollution, for checking food quality, and for the medical diagnosis of certain diseases.

[0003] Various methods have been developed to detect amines, including spectroscopy, chromatography, and electrochemistry, but these methods have problems with low sensitivity and selectivity. On the other hand, fluorescent sensors using fluorescent substances have attracted attention because they are highly sensitive, highly selective, reversible, and capable of high-speed response. For example, Patent Document 1 describes a method for detecting amines using a tetraphenylethene derivative as a fluorescent substance. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2018-119068 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, the fluorescent substance described in Patent Document 1 emits light when the fluorescent tetraarylethene derivative aggregates in the presence of an amine, and therefore, when the concentration of the amine is low, the aggregation of the tetraarylethene derivative tends to be insufficient, making it difficult to detect the amine.

[0006] The present invention aims to solve these problems and provide an amine detection method using a fluorescent substance, in which light emission changes due to PET activity, in which an intermolecular hydrogen bond is formed between the amine and a boronic acid group (-B(OH)2), and the amount of fluorescence quantum change before and after reaction with the amine is large even when the amine concentration is low, thereby enabling amine detection with high sensitivity and good reproducibility. [Means for solving the problem]

[0007] As a result of extensive investigations aimed at solving the above problems, the present inventors have found that a specific fluorescent substance exhibits a large change in fluorescence quantum before and after reaction with an amine, and thus can solve the above problems.

[0008] That is, the present invention relates to the following.

[0009] [1] A method for detecting an amine, comprising: A method for detecting an amine, comprising the steps of: detecting an amine from the difference between a maximum fluorescence intensity X1 of a fluorescent substance represented by the following formula 1 before contacting the amine with the amine and a maximum fluorescence intensity X2 of the fluorescent substance after contacting the fluorescent substance with the amine:

[0010] [ka]

[0011] (In formula 1, R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted benzyl group, or an optionally substituted aryl group, A is a spacer. Z represents an atomic group that exhibits fluorescence emission upon photoexcitation.

[0012] [2] The method for detecting an amine according to [1], wherein Z is an atomic group having a skeleton selected from the group consisting of anthracene, pyrene, coumarin, BODIPY, and xanthene.

[0013] [3] The method for detecting an amine according to [1] or [2], wherein A is an aromatic hydrocarbon group or a heterocyclic group. [4] The method for detecting an amine according to any one of [1] to [3], wherein the group adjacent to the nitrogen atom in formula 1 among Z is an alkylene group having 1 to 4 carbon atoms or a phenylene group.

[0014] [5] The method for detecting an amine according to any one of [1] to [4], wherein the fluorescent substance represented by the formula 1 has a structure represented by the following formula 2:

[0015] [ka]

[0016] [6] The method for detecting an amine according to any one of [1] to [5], wherein the amine is a secondary or tertiary amine.

[0017] [7] The method for detecting an amine according to any one of [1] to [6], wherein the fluorescent substance represented by the formula 1 is formed on a film surface.

[0018] [8] The method for detecting an amine according to any one of [1] to [6] above, wherein the fluorescent substance represented by the formula 1 is kneaded into a resin composition.

[0019] [8] A method for detecting an amine in a measurement sample, comprising: A step of preparing a solution B by dissolving a fluorescent substance represented by the following formula 1 in a solvent A; Measuring the maximum fluorescence intensity X1 of the solution B; and measuring a maximum fluorescence intensity X2 after adding the measurement sample to the solution B.

[0020] [ka]

[0021] (In formula 1, R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted benzyl group, or an optionally substituted aryl group, A is a spacer. Z represents an atomic group that exhibits fluorescence emission upon photoexcitation. Effect of the Invention

[0022] According to the method for detecting an amine of the present invention, the amine can be detected with high sensitivity and good reproducibility by using a fluorescent substance that exhibits a large change in fluorescence intensity before and after contact with an amine. [Brief description of the drawings]

[0023] [Figure 1] 1 is a chart showing the fluorescence spectrum measured in Example 1. [Diagram 2] 1 is a chart showing the fluorescence spectrum measured in Example 2. [Diagram 3] 1 is a chart showing the fluorescence spectrum measured in Example 3. [Figure 4] 1 is a chart showing the fluorescence spectrum measured in Example 4. [Diagram 5] 1 is a chart showing the fluorescence spectrum measured in Example 5. [Figure 6] 1 is a chart showing the fluorescence spectrum measured in Example 6. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described in detail below with reference to the preferred embodiments.

[0025] [Amine detection method] The amine detection method of the present invention is a method for detecting an amine based on the difference between the maximum fluorescence intensity X1 of a fluorescent substance represented by the following formula 1 (hereinafter sometimes referred to as the "fluorescent substance of the present invention") before contacting the amine and the maximum fluorescence intensity X2 after contacting the amine.

[0026] [ka]

[0027] (In formula 1, R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted benzyl group, or an optionally substituted aryl group, A is a spacer. Z represents an atomic group that exhibits fluorescence emission upon photoexcitation.

[0028] <Mechanism> The fluorescent substance of the present invention is inactive in terms of photo-induced electron transfer (PET) due to intramolecular hydrogen bonds before it comes into contact with an amine, and therefore emits fluorescence when irradiated with ultraviolet light. In contrast, when the fluorescent substance of the present invention comes into contact with an amine, an intermolecular hydrogen bond is formed between the amine and the boronic acid group (-B(OH)2) in formula 1, resulting in PET activity and quenching the fluorescence even when irradiated with ultraviolet light. As a result, the fluorescent substance of the present invention has a maximum fluorescence intensity X2 after contact with an amine which is smaller than the maximum fluorescence intensity X1 before contact with an amine, and the presence of an amine can be detected from the difference between these (maximum fluorescence intensity X1-maximum fluorescence intensity X2). In general, the maximum fluorescence intensity X2 tends to decrease as the amount of amine present increases and the amount of intermolecular hydrogen bonds with the fluorescent substance of the present invention increases. Therefore, based on the difference between the maximum fluorescence intensity X1 and the maximum fluorescence intensity X2, it is possible not only to detect the amine but also to quantitatively determine the amount of amine present to some extent.

[0029] The fluorescence intensity of the fluorescent substance of the present invention can be measured using a general fluorescence spectrum measuring device.

[0030] <Fluorescent substances> In the above formula 1 which represents the fluorescent substance of the present invention, R is a hydrogen atom, an alkyl group which may have a substituent, a benzyl group which may have a substituent, or an aryl group which may have a substituent. From the viewpoint of solubility, R is preferably an alkyl group which may have a substituent. In this case, from the viewpoint of solubility, the number of carbon atoms in the alkyl group is preferably 1 to 20, particularly preferably 1 to 5, and the alkyl group is most preferably a methyl group. In addition, when the alkyl group has a substituent, examples of the substituent include an alkoxy group, a fluorine atom, a carboxyl group, etc., but it is preferable that the alkyl group of R has no substituent from the viewpoint of fluorescence deactivation.

[0031] A is a spacer. As long as A functions as a spacer, it is not particularly limited, and examples thereof include -O- (oxygen atom), -CH2- (methylene group), -CH2-C6H4- (methylenephenylene group), and the like. From the viewpoint of electron transfer, A is preferably an aromatic hydrocarbon group or a heterocyclic group, more preferably a methylenephenylene group, and the benzene ring of the methylenephenylene group may have a substituent such as a cyano group, a trifluoromethyl group, or an acetyl group.

[0032] Z is an atomic group that exhibits fluorescent emission upon photoexcitation. The atomic group that exhibits fluorescence emission upon photoexcitation may be one that can be confirmed to have a luminescence quantum yield of 2% or more, calculated using the following formula from the number of absorbed photons and the number of fluorescent photons measured using a method conforming to JIS R 1697:2015. Luminescence quantum yield (%) = Number of fluorescent photons / Number of absorbed photons x 100 Examples of such atomic groups include those having a skeleton of anthracene, pyrene, coumarin, BODIPY (boron-dipyrromethene), xanthene, porphyrin, pyrrolopyrrol cyanine (PPCy), cyanine dye, phthalocyanine, rhodamine, etc. From the viewpoint of luminous efficiency, atomic groups having a skeleton selected from the group consisting of anthracene, pyrene, coumarin, BODIPY, and xanthene are preferred.

[0033] From the viewpoint of ease of photoinduced electron transfer, the group adjacent to the nitrogen atom in formula 1 among Z is preferably an alkylene group having 1 to 4 carbon atoms or a phenylene group.

[0034] In terms of photoinduced electron transfer properties, the fluorescent substance of the present invention is preferably a fluorescent substance having a structure represented by the following formula 2, but is not limited thereto.

[0035] [ka]

[0036] Such a fluorescent substance of the present invention can be produced, for example, by the method described in J. Am. Chem. Soc. 2017, 139, 5568-5578. In addition, the fluorescent substance having the structure represented by the formula 2 can be produced, for example, by the method described in New J. Chem., 2022, 46, 21037-21046.

[0037] <Amine> In terms of reactivity with the fluorescent substance of the present invention, examples of the amines to be detected in the present invention include alkylamines, arylamines, and amines of heterocyclic compounds having a nitrogen atom, each of which has a pKa of 6 or more, preferably 7 or more, and more preferably 8 or more.

[0038] Specific examples of amines to be detected in the present invention include primary amines such as ethylamine, phenethylamine, and aniline; secondary amines such as diethylamine and N-methyltyramine; and tertiary amines such as triethylamine, dimethyltryptamine, and pyridine, but are not limited to these and include biogenic amines.

[0039] Of these, the amine to be detected is preferably a secondary or tertiary amine from the viewpoint of basicity.

[0040] <Amine detection method> There are no particular limitations on the specific method for carrying out the amine detection method of the present invention, but the method can be carried out by the amine detection method of the present invention, which includes the steps of preparing solution B by dissolving the fluorescent substance of the present invention in solvent A, measuring the maximum fluorescence intensity X1 of solution B, and adding a measurement sample containing the amine to be detected to solution B and measuring the maximum fluorescence intensity X2.

[0041] In this case, the solvent A may be any solvent capable of dissolving the fluorescent substance of the present invention, and is not particularly limited thereto. Examples of the solvent A include protic solvents such as water and alcohol, water-soluble aprotic solvents such as acetonitrile, and mixed solvents thereof.

[0042] The concentration of the fluorescent substance of the present invention in the solution B is preferably 1 μM or more and 500 μM or less. If the fluorescent substance concentration is equal to or more than the lower limit, sufficient fluorescence intensity can be obtained. If the fluorescent substance concentration is equal to or less than the upper limit, problems such as precipitation of the fluorescent substance can be suppressed. A more preferable concentration of the fluorescent substance is 10 μM or more and 50 μM or less. Note that μM is 10 -6 Expressed in mol / L.

[0043] There is no particular restriction on the amount of the measurement sample added to solution B, but it is preferable that the amine equivalent (molar number) is 1 to 10 equivalents, particularly 1 to 8 equivalents. If the amine equivalent is equal to or greater than the lower limit, the maximum fluorescence intensity X2 can be made smaller than the maximum fluorescence intensity X1, and the detection accuracy of the amine can be improved. If the amine equivalent is equal to or less than the upper limit, the detection sensitivity of the amine can be improved.

[0044] <Fluorescent substance form> In the present invention, in addition to dissolving a fluorescent substance in a solvent and contacting it with the amine to be detected, the amine to be detected can be contacted with a film having a fluorescent substance formed on its surface or a resin composition into which a fluorescent substance has been kneaded, and the amine can be detected from the maximum fluorescence intensity X1 before contact with the amine and the maximum fluorescence intensity X2 of the fluorescent substance after contact with the amine. More specifically, the fluorescent substance of the present invention can be used by forming a film on the surface of a substrate such as a resin such as polyvinyl alcohol (PVA), polymethyl methacrylate (PMMA), polyethylene terephthalate (PET), polycarbonate (PC), glass, or metal.

[0045] The substrate is preferably a PVA film. For example, a PVA film can be immersed in the solution containing the fluorescent substance of the present invention, then removed, washed with methanol or the like, and dried to form a film.

[0046] When a fluorescent film thus formed is used, the amine may be detected by immersing the fluorescent film in an amine-containing solution and observing the change in maximum fluorescence intensity before and after the immersion, or by exposing the fluorescent film to amine vapor and observing the change in maximum fluorescence intensity before and after the exposure. In either case, the fluorescent substance of the present invention formed on a substrate forms intermolecular hydrogen bonds between the substrate and the fluorescent substance in a dry state, resulting in a PET inactive state and fluorescent emission. However, upon contact with an amine, this intermolecular hydrogen bond is broken, resulting in a PET active state and quenching of the fluorescence. EXAMPLES

[0047] The present invention will be described more specifically below with reference to examples.

[0048] [Fluorescence intensity measurement method] The fluorescence intensity of each of the fluorescent substances or films thereof in the Examples and Comparative Examples was measured using the following apparatus and conditions. Fluorescence spectrum measuring device: HITACHI F-4500 <Measurement conditions> Scan speed: 1200nm / min Excitation side slit: 5.0 nm Fluorescence side slit: 5.0 nm Photomultiplier: 400V Response time: 0.004s

[0049] [Fluorescent material] The fluorescent substances used for the evaluation were synthesized in the following manner.

[0050] <Production Example 1: Synthesis of fluorescent substance (TF-2)> Anthracene-AminoMeCN-PhenylB(OH)2 (TF-2) was synthesized from 3-(((anthracen-9-ylmethyl)(methyl)amino)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (OF-2) by the method shown below.

[0051] (Synthesis of OF-2) [ka]

[0052] 4-bromo-3-methylbenzonitrile (2.0g, 10.2mmol), bis(pinacolato)diboron (2.58g, 10.2mmol), potassium acetate (2.0g, 20.4mmol) and PdC12(dppf) (0.24g, 0.3mmol) were dissolved in N,N-dimethylformamide (30ml) and stirred at 80°C for 24 hours under argon atmosphere. Water was added to the reaction mixture and the aqueous layer was extracted with dichloromethane. After vacuum concentration, the resulting concentrate was separated by silica gel column chromatography (developing solvent: dichloromethane) to obtain compound 2 as a white solid (1.85g, yield 75%). The analytical results of compound 2 are as follows: mp:135-137℃ IR(ATR):ν ~ =2234,1605,1346,1134cm -1 1 HNMR(400MHz,acetone-d6):δ=1.37(s,12H),2.57(s,3H),7.55-7.57(m,2H),7.85(d,J=7.6Hz,1H)ppm HRMS(APCI):m / z(%):[M+H+]calcd for C14H 19 BNO2:244.15034 found:244.15030

[0053] Next, the compound 2 (0.5 g, 2.1 mmol), N-bromosuccinimide (0.37 g, 2.1 mmol), and benzoylperoxide (0.003 g, 0.01 mmol) were dissolved in carbon tetrachloride (5 ml), and the solution was stirred at 80° C. for 24 hours under an argon atmosphere. The reaction mixture was separated and concentrated, dissolved in ethyl acetate, and washed with 0.5M HCl aqueous solution and water. The obtained organic extract was dried over MgSO4, separated, concentrated, and reprecipitated with dichloromethane-hexane to obtain compound 3 (0.34 g, yield 52%) as a white powder. The analytical results of compound 3 are as follows: MP:108-110℃ IR(ATR):ν ~ =2234,1607,1346,1142cm -1 1 HNMR(400MHz,acetone-d6):δ=1.41(s,12H),5.00(s,2H),7.73(dd,J=1.6 and 7.7Hz,1H),7.89(d,J=1.6Hz,1H),7.93(d,J=7.7Hz,1H)ppm HRMS(APCI):m / z(%):[M+H+]calcd for C14H 18 BNO2Br:322.06085 found:322.06085

[0054] Next, 9-(methylaminomethyl)anthracene (0.17 g, 0.62 mmol), the compound 3 (0.2 g, 0.6 mmol), and Na2CO3 (0.26 g, 2.5 mmol) were dissolved in N,N-dimethylformamide (5 ml) and stirred at room temperature for 24 hours under an argon atmosphere. Water was added to the reaction mixture, and the aqueous layer was extracted with dichloromethane. The organic extract was dried over MgSO4, separated, and concentrated. The obtained substance was dissolved in toluene and purified by high performance liquid chromatography to obtain a yellow solid of OF-2 (0.03 g, yield 10%). The results of the OF-2 analysis are as follows: MP:129-131℃ IR(ATR):ν ~ =2228,1605,1342,1136cm -1 1 HNMR(400MHz,acetone-d6):δ=1.29(s,12H),2.28(s,3H),4.01(s,2H),4.47(s,2H),7.47-7.54(m,4H),7.65(dd,J=1.6 and 7.6Hz,1H),7.75(d,J=1.0Hz,1H),7.89(d,J=7.6Hz,1H),8.04-8.06(m,2H),8.39(d,J=8.8Hz,2H),8.51(s,1H)ppm HRMS(APCI):m / z:[M+H+]calcd for C30H 32 BN2O2:463.25514 found:463.25510 Anal.calcd for C30H 31 BN2O2: C77.93, H6.76, N6.06 Found:C77.67,H6.74,N5.92

[0055] (Synthesis of TF-2) [ka]

[0056] OF-2 (50 mg, 0.10 mmol) was dissolved in water / EtOH = about 1 / 3 (v / v), filtered and allowed to stand to give TF-2 as white crystals (13 mg, 32%). The anthracene skeleton of TF-2 is a known atomic group that exhibits fluorescent emission, and the emission quantum yield is 2% or more. The results of the TF-2 analysis are as follows: MP:177-180℃ FT-IR(ATR):υ ~ =2227,1346,1294,1195,889,732,601cm -1 1 HNMR(500MHz,acetonitrile-d3):2.35(s,3H),3.96(s,2H),4.96(s,2H),7.29-7.33(m,2H),7 .42-7.46(m,2H),7.53-7.57(m,2H),7.97(d,J=7.5Hz,1H),8.03-8.10(m,4H),8.56(s,1H)ppm 13 CNMR(125MHz,acetonitrile-d3):δ=42.06,51.85,63.10,112.47,119.83,125.63,125.98,1 26.91,128.72,129.44,129.84,130.13,131.16,131.73,131.82,133.93,136.09,144.14ppm HRMS(ESI):m / z(%):[M+H + ]calcd for C 24 H 22 N2O2B:381.17688 found:381.17675

[0057] [Example 1] A 20 μM solution of a fluorescent substance (TF-2) was prepared by dissolving it in a mixed solvent of acetonitrile and water (1:1), and the fluorescence spectrum of the solution was measured before adding ethylamine (EA) (pKa: 10.6). Next, ethylamine was added to each of the solutions to give the concentrations shown in Table 1 below, and the fluorescence spectrum was measured. The maximum fluorescence intensity was obtained from the measurement results of the fluorescence spectrum, and the difference was calculated. The results are shown in FIG. In FIG. 1, the fluorescence intensity curves are in the order of TF-2, EA1, EA2, EA3, EA5, EA8, EA10, EA20, EA30, EA40, and EA50 from the top. As shown in FIG. 1 and Table 1, the addition of ethylamine reduces the maximum fluorescence intensity depending on the concentration of the ethylamine added.

[0058] [Table 1]

[0059] [Example 2] The measurement was carried out in the same manner as in Example 1, except that diethylamine (DEA) (pKa: 10.9) was used instead of ethylamine. The results are shown in FIG. In Figure 2, the fluorescence intensity curves are in the following order from top to bottom: TF-2, DEA1, DEA2, DEA3, DEA5, DEA8, DEA10, DEA20, DEA30, DEA40, and DEA50.

[0060] [Table 2]

[0061] [Example 3] The measurement was carried out in the same manner as in Example 1, except that triethylamine (TEA) (pKa: 11.9) was used instead of ethylamine. The results are shown in FIG. In FIG. 3, the fluorescence intensity curves are in the following order from top to bottom: TF-2, TEA1, TEA2, TEA3, TEA5, TEA8, TEA10, TEA20, TEA30, TEA40, and TEA50.

[0062] [Table 3]

[0063] It can also be seen from the results in Table 2 and FIG. 2 and Table 3 and FIG. 3 that the maximum fluorescence intensity tends to decrease with an increase in the concentration of amine present in the solution.

[0064] [Example 4] <Fabrication of PVA Film> A polyvinyl alcohol (PVA) film with its surface modified by a fluorescent substance (TF-2) was fabricated according to the following procedure. (1) PVA (0.24 g) was added to water (4 mL) and dissolved at 80 °C. (2) 0.3 mL of the PVA solution was dropped onto a silicon substrate, heated to 80 °C, and left standing for 24 hours to fabricate a PVA film. (3) The fabricated PVA film on the silicon substrate was immersed in a solution of the fluorescent substance (TF-2) (2.0×10 -5 M) dissolved in methanol and held for 24 hours. (4) The silicon substrate with the PVA film was taken out of the TF-2 solution, washed with methanol, and then dried.

[0065] <Measurement of TF-2 Adsorption Amount> A calibration curve was prepared by measuring the absorption spectra of TF-2 solutions with several concentrations. For the residual solution of the TF-2 solution when the PVA film was fabricated in the above <Fabrication of PVA Film>, the absorption spectrum was measured, and the amount of TF-2 adsorbed on the film was calculated. As a result, it was confirmed that about 2 mass% of TF-2 was adsorbed on the fabricated PVA film.

[0066] <Detection of Triethylamine> The fabricated TF-2-adsorbed PVA film was exposed to triethylamine (TEA) vapor, and the fluorescence spectra before and after that were measured to evaluate the triethylamine sensitivity. The results are shown in Figure 4. As shown in Figure 4, when the TF-2-adsorbed PVA film is exposed to triethylamine vapor, the fluorescence intensity decreases.

[0067] [Example 5] Using pyridine (pKa: 5.3) instead of triethylamine, the pyridine sensitivity was evaluated in the same manner as in Example 4. The results are shown in Figure 5.

[0068] [Example 6] The aniline sensitivity was evaluated in the same manner as in Example 4, except that aniline (pKa: 4.6) was used instead of triethylamine. The results are shown in Figure 6.

[0069] As shown in Figures 5 and 6, the fluorescence intensity also decreased when the TF-2-adsorbed PVA film was exposed to pyridine or aniline vapor.

[0070] From the above results, it is apparent that amines can be detected with high sensitivity and good reproducibility by using the fluorescent substance of the present invention. [Industrial Applicability]

[0071] According to the amine detection method of the present invention, amines can be detected with high sensitivity, high selectivity, good reproducibility and high response, and is expected to be used in monitoring air pollution and environmental pollution, food quality checks, medical diagnosis of specific diseases, etc.

Claims

1. 1. A method for detecting an amine, comprising: A method for detecting an amine, comprising the steps of: detecting an amine from the difference between a maximum fluorescence intensity X1 of a fluorescent substance represented by the following formula 1 before contacting the amine with the amine and a maximum fluorescence intensity X2 of the fluorescent substance after contacting the fluorescent substance with the amine: 【Chemistry 1】 (In formula 1, R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted benzyl group, or an optionally substituted aryl group, A is a spacer, Z represents an atomic group that exhibits fluorescent emission upon photoexcitation.

2. 2. The method for detecting an amine according to claim 1, wherein said Z is an atomic group having a skeleton selected from the group consisting of anthracene, pyrene, coumarin, BODIPY, and xanthene.

3. The method for detecting an amine according to claim 1 , wherein A is an aromatic hydrocarbon group or a heterocyclic group.

4. 2. The method for detecting an amine according to claim 1, wherein the group adjacent to the nitrogen atom in formula 1 among Z is an alkylene group having 1 to 4 carbon atoms or a phenylene group.

5. The method for detecting an amine according to claim 1 , wherein the fluorescent substance represented by formula 1 has a structure represented by formula 2 below: 【Chemistry 2】

6. The method for detecting an amine according to claim 1 , wherein the amine is a secondary or tertiary amine.

7. The method for detecting an amine according to claim 1 , wherein the fluorescent substance represented by formula 1 is formed as a film on a surface of the film.

8. The method for detecting an amine according to claim 1 , wherein the fluorescent substance represented by the formula 1 is kneaded into a resin composition.

9. 1. A method for detecting an amine in a measurement sample, comprising the steps of: A step of preparing a solution B by dissolving a fluorescent substance represented by the following formula 1 in a solvent A; Measuring the maximum fluorescence intensity X1 of the solution B; and measuring a maximum fluorescence intensity X2 after adding the measurement sample to the solution B. 【Chemistry 3】 (In formula 1, R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted benzyl group, or an optionally substituted aryl group, A is a spacer, Z represents an atomic group that exhibits fluorescent emission upon photoexcitation.

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