JP4869871B2 - Mercapto group-containing substance detection apparatus and method - Google Patents

Description

  The present invention relates to an apparatus and method for detecting a mercapto group-containing substance.

Malodorous components such as toilets and kitchens are substances having mercapto groups (SH groups) such as methyl mercaptan (CH ₃ -SH) and hydrogen sulfide (H-SH). There is a need for an apparatus that can detect a gas concentration of a substance within a range of several ppb to several ppm.
Therefore, as a detection device for detecting hydrogen sulfide and mercaptans, one using an oxide semiconductor as a sensitive layer has been proposed (for example, see Patent Document 1). In addition, a detection device using an oxine metal complex or a porphyrin metal complex as a fluorescent substance has been proposed (see, for example, Patent Document 2).
On the other hand, 2-pyridylaminoethylmaleimide hydrochloride and the like are known as a compound for fluorescently labeling a substance having a thiol group, and this compound has a property of emitting fluorescence by binding to a thiol group (for example, , See Patent Document 3).

JP 2004-245726 A JP-A-4-335141 JP-A-6-122679

In the conventional detection device using an oxide semiconductor described in Patent Document 1, since the sensitivity is low, a limit concentration of a human olfactory mercapto group-containing substance, for example, a concentration of about 0.7 ppb as a concentration of methyl mercaptan can be detected. In addition, since the oxide semiconductor also reacts with the aromatic volatile organic compound, there is a problem that the distinguishability is low.
The conventional detection device described in Patent Document 2 has a problem that the sensitivity cannot be sufficiently obtained because the fluorescence intensity decreases as the malodorous substance concentration increases.
Patent Document 3 does not describe any application of 2-pyridylaminoethylmaleimide hydrochloride or the like to a detection device.
Accordingly, the present invention has been made to solve the above-described problems, and has high discrimination with respect to mercapto group-containing substances such as methyl mercaptan and hydrogen sulfide, and can be detected with high sensitivity. The object is to obtain a mercapto group-containing substance detection device.

で表されることを特徴とする。
また、この発明に係るメルカプト基含有物質検知方法は、マレイミド基が直接または他の機能原子団を介して蛍光機能団に結合され、メルカプト基含有物質と反応することにより蛍光収率が増大する蛍光物質とメルカプト基含有物質とを反応させ、その反応生成物を励起したときの蛍光光度を測定し、測定された蛍光光度に基づいてメルカプト基含有物質の濃度を求めるものであり、前記蛍光物質が、下記式：

で表されることを特徴とする。 The mercapto group-containing substance detection device according to the present invention includes a fluorescent substance in which a maleimide group is bonded to a fluorescent functional group directly or via another functional atomic group and reacts with the mercapto group-containing substance to increase the fluorescence yield. , A reaction part for reacting the fluorescent substance and the mercapto group-containing substance, a light source for irradiating the reaction product of the fluorescent substance and the mercapto group-containing substance with excitation light, and receiving the fluorescence emitted by the reaction product, a fluorescence detecting section for outputting an electric signal corresponding to the intensity state, and are not provided with a calculation unit for calculating the concentration of the mercapto group-containing material based on an electric signal output from the fluorescence detection unit, the fluorescent substance The following formula:

It is represented by .
Further, the mercapto group-containing substance detection method according to the present invention is a fluorescence in which a maleimide group is bonded to a fluorescent functional group directly or via another functional atomic group and reacts with the mercapto group-containing substance to increase the fluorescence yield. reacting the material with a mercapto group-containing material state, and are not seeking fluorometer to measure the concentration of the mercapto group-containing material based on the measured fluorescence intensity when excited and the reaction product, the fluorescent substance But the following formula:

It is represented by .

  According to the present invention, it is possible to provide a mercapto group-containing substance detection device and method which have high discrimination with respect to mercapto group-containing substances such as methyl mercaptan and hydrogen sulfide and can detect with high sensitivity.

Hereinafter, embodiments of the present invention will be described with reference to the drawings.
Embodiment 1 FIG.
FIG. 1 is a diagram for explaining a configuration of a mercapto group-containing substance detection device according to Embodiment 1 of the present invention. In FIG. 1, the mercapto group-containing substance detection apparatus according to the first embodiment has a fluorescence yield obtained by reacting a maleimide group with a fluorescent functional group directly or via another functional atomic group and reacting with the mercapto group-containing substance. Fluorescence generated by a reaction product of a reaction part 1 made of a fluorescent film containing a fluorescent substance that increases in intensity, a light source 2 arranged to irradiate the fluorescent film with excitation light, and a reaction product of the fluorescent substance and a mercapto group-containing substance Is disposed between the reaction unit 1 and the fluorescence detection unit 3, and absorbs or reflects the excitation light L1 from the light source 2 and transmits the fluorescence signal. And an optical filter 4 that selectively transmits the fluorescence L2 emitted from the reaction product, and a calculation unit 5 that calculates the concentration of the mercapto group-containing substance based on the electrical signal output from the fluorescence detection unit 3. That. The reaction unit 1 is formed on a substrate 6 such as an aluminum plate or a glass plate. The reaction unit 1 is disposed in a reaction cell 9 that can transmit the excitation light L1 from the light source 2 and the fluorescence L2 emitted from the reaction product. The reaction cell 9 is used for introducing a sample gas. A sample gas introduction pipe 7 and a sample gas discharge pipe 8 are connected to discharge the sample gas. Furthermore, the fluorescence detection unit 3 includes a light receiving element 10 and a light detection circuit board 11, and the light detection circuit board 11 is connected to the calculation unit 5 through a signal line. The fluorescent functional group of the fluorescent substance used here preferably has a porphyrin skeleton, pyrene skeleton or coumarin skeleton, and more preferably a porphyrin skeleton.

Next, a method for detecting a mercapto group-containing substance of the mercapto group-containing substance detection apparatus configured as described above will be described. First, the sample gas is introduced into the reaction cell 9 through the sample gas introduction pipe 7. When the sample gas contains a mercapto group-containing substance such as methyl mercaptan, the mercapto group-containing substance reacts with the fluorescent substance, and the reaction product is excited by the excitation light L1 emitted from the light source 2 to become fluorescent. L2 is emitted. The fluorescence L2 emitted here passes through the optical filter 4 and enters the light receiving element 10, and the light receiving element 10 outputs an electrical signal (voltage or current) corresponding to the fluorescence intensity. The light source 2 only needs to be able to sufficiently excite a fluorescent substance in which a maleimide group is bonded to a fluorescent functional group directly or through another functional atomic group, and is preferably ultraviolet light or visible light. From the viewpoint of reduction, visible light in the wavelength range of 400 to 450 nm is more preferable.
For example, as a fluorescent substance in which a maleimide group is bonded to a fluorescent functional group directly or through another functional atomic group, the following formula (1):

で表される化合物（ポルフィリン骨格を有する化合物）を用いる場合、中心波長４３０ｎｍの青色光を照射できる青色発光ダイオードを光源２として用いることで、反応生成物（メルカプトマレイミドポルフィリン）が約６２０ｎｍにピークを有する赤色の蛍光を発するようになる。この蛍光の波長は、代表的な受光素子であるフォトダイオードの最も感度の高い領域であるため、低コストで高感度の検出が可能となる。

When a compound represented by the formula (compound having a porphyrin skeleton) is used, a blue light emitting diode capable of irradiating blue light with a central wavelength of 430 nm is used as the light source 2, so that the reaction product (mercaptomaleimide porphyrin) has a peak at about 620 nm. It has red fluorescence. Since the fluorescence wavelength is the most sensitive region of a photodiode, which is a typical light receiving element, detection with high sensitivity is possible at low cost.

Next, the electrical signal output from the light receiving element 10 is sent to the light detection circuit board 11, amplified there, and then sent to the calculation unit 5. The computing unit 5 calculates the concentration of the mercapto group-containing substance in the sample gas based on the transmitted electrical signal. As a method for calculating the concentration of the mercapto group-containing substance here, for example, using the fact that there is a correlation between the fluorescence intensity and the concentration of the mercapto group-containing substance in the sample gas, For example, a calibration curve showing a relationship with voltage or current is prepared in advance, and the electric signal sent and the calibration curve are compared to obtain. When such a calculation method is adopted, it is desirable that the calculation unit 5 has a function of storing the transmitted electric signal, a function of comparing with a calibration curve, and the like.
On the other hand, a part of the excitation light L1 is reflected or scattered by the fluorescent film or the reaction cell 9 and becomes reflected / scattered light L3 toward the light receiving element 10, but is blocked (cut) by the optical filter 4 and received by the light receiving element 10. Is hardly incident. Although the light receiving element 10 generally has a wavelength dependency but outputs an electric signal when light is incident, the optical filter 4 is disposed in the optical path of the reflected / scattered light L3 as in the present embodiment. Therefore, it is possible to detect the intensity of fluorescence with high sensitivity while suppressing the influence of excitation light. In the case of the configuration using the fluorescent substance and the blue light emitting diode as described above, the optical filter 4 is a blue cut filter (for example, a band pass filter that transmits only red light or a low pass filter that blocks only blue light). May be arranged between the fluorescent film and the light receiving element 10 at a position where the excitation light L1 irradiated from the light source 2 to the fluorescent film is not shielded as much as possible. The above-described filter is realized by using a dye or using a vapor deposition laminated film. Note that some types of light emitting diodes emit near-infrared rays of about 1000 nm. Therefore, when such a light-emitting diode is used as the light source 2, an infrared cut filter or a near-infrared cut filter is used as a blue light cut filter. It is desirable to stack them or to arrange them appropriately between the light source 2 and the fluorescent film.

Thus, according to the first embodiment, since the concentration of the mercapto group-containing substance is calculated from the fluorescence intensity when the reaction product of the specific fluorescent substance and the mercapto group-containing substance is excited, the mercapto group-containing substance is calculated. A mercapto group-containing substance can be detected with high sensitivity with little influence from substances other than substances.
Such a mercapto group-containing substance detection device can be suitably used as a rot monitor in food storage such as a refrigerator or a cold and dark room, a odor monitor indoors or outdoors, or a leak detector for gas odorized with a mercapto group-containing substance. In addition, the present invention can be applied to operation control of an air purifier or a ventilator that operates only when a bad odor occurs.

Embodiment 2. FIG.
FIG. 2 is a diagram for explaining the configuration of a mercapto group-containing substance detection device according to Embodiment 2 of the present invention. In FIG. 2, in the mercapto group-containing substance detection device according to Embodiment 2, the optical filter 4 and the reaction part 1 made of a fluorescent film are stacked in this order on the light receiving surface of the light receiving element 10, and the reaction part 1, the optical filter 4 and the fluorescence detection part 3 are integrated. Therefore, the fluorescence emitted from the reaction product is efficiently incident on the light receiving element 10. Of the light receiving element 10, the optical filter 4 and the fluorescent film, only the fluorescent film is disposed in the reaction cell 9. The light source 2 is disposed on the opposite side of the surface in contact with the optical filter 4 so that the fluorescent film can be irradiated with excitation light. From the viewpoint of obtaining higher sensitivity, it is preferable that the light receiving surface of the light receiving element, the optical filter 4, and the fluorescent film are closely stacked in parallel. Since other configurations and detection methods are the same as those of the mercapto group-containing substance detection device according to the first embodiment, in this embodiment, the same parts as those in FIG. To do.

Since the fluorescence emitted from the reaction product is emitted in all directions, the fluorescence intensity incident on the light receiving element decreases as the distance between the light receiving surface of the light receiving element and the fluorescent film increases, but the light is received as in the second embodiment. By sequentially laminating an optical filter and a fluorescent film on the light receiving surface of the element, fluorescence emitted from the reaction product is efficiently incident on the light receiving element, so that a mercapto group-containing substance can be detected with extremely high sensitivity. .
In the second embodiment, the fluorescent film is disposed in the reaction cell 9, but as shown in FIG. 3, a hole 12 is appropriately provided on the bottom surface of the reaction cell 9 so that the sample gas can come into contact with the fluorescent substance. You may arrange | position so that a fluorescent film may closely_contact | adhere via the O ring 13 grade | etc., To a bottom face. By arranging the fluorescent film outside the reaction cell 9 in this way, the fluorescent film can be easily exchanged.

Embodiment 3 FIG.
In the mercapto group-containing substance detection device according to Embodiment 3, a fluorescent substance solution formed by dissolving or suspending a fluorescent substance in a hardly volatile organic solvent is contained in a reaction cell from a fluorescent substance solution holding unit held on a support. The reaction part is arranged in place of the substrate 6 and the reaction part 1 formed thereon in FIG. The hardly volatile organic solvent used here may be any one that can dissolve or suspend a fluorescent substance and hardly volatilize, and examples thereof include dimethyl sulfoxide. The fluorescent substance is desirably dissolved or suspended in a hardly volatile organic solvent so as to be close to a saturated concentration from the viewpoint of further increasing the fluorescence intensity. In addition, as a support for holding the fluorescent substance solution, filter paper or nonwoven fabric made of fibers such as cellulose, acetylcellulose, glass fiber, glass-coated silica substrate (usually used for thin-layer chromatography), aluminum plate, Examples of the glass plate include micropores formed by electrolysis or hydrofluoric acid dissolution. The fluorescent substance solution holding part can be formed by dropping, applying, or impregnating the fluorescent substance solution to these supports. What is necessary is just to form. The fluorescent substance solution holding part may be fixed in a frame, or may be adhered to a substrate such as an aluminum plate or a glass plate. Other configurations and detection methods are the same as those of the mercapto group-containing substance detection device according to the first embodiment, and thus the description thereof is omitted in this embodiment.

  According to the third embodiment, since the fluorescent substance is in a free state in the hardly volatile organic solvent, it is possible to increase the conveyance speed and the fluorescence yield with the mercapto group-containing substance, and to achieve higher sensitivity. Can detect a mercapto group-containing substance.

Since the effect of the present invention has been confirmed by experiments, the contents thereof will be specifically described below.
<Example 1>
[Synthesis of fluorescent substance (maleimidoporphyrin)]
5,10,15,20-tetrakis- (4-aminophenyl) -21H, 23H-porphine (Tokyo Chemical Industry Co., Ltd.) 100 mg (0.148 mmol) and maleic anhydride (Tokyo Chemical Industry Co., Ltd.) 145 mg ( 1.48 mmol) was added to 500 ml of dichloromethane (manufactured by Kanto Chemical Co., Inc.) and refluxed for 24 hours. After allowing to cool, the precipitate was collected by suction filtration. Furthermore, it was dried under vacuum to obtain an intermediate.
20 mg (0.02 mmol) of the obtained intermediate and 50 mg (0.38 mmol) of zinc chloride (manufactured by Kanto Chemical Co., Ltd.), 27 ml of benzene (manufactured by Kanto Chemical Co., Ltd.) and N, N-dimethylformamide (Kanto Chemical Co., Ltd.) (Product made) In addition to the mixed solution with 3 ml, a suspension solution was prepared. When 1,1,1,3,3,3-hexamethyldisilazane (Tokyo Chemical Industry Co., Ltd.) 400 μl (1.89 mmol) was added to this solution, the solution became transparent. Reflux was performed for 10 hours. After allowing to cool, the precipitate was removed by suction filtration, and benzene in the filtrate was distilled off under reduced pressure. The remaining N, N-dimethylformamide solution was poured into cold water and cooled. The resulting precipitate was collected by suction filtration. Furthermore, it dried under vacuum and the maleimide porphyrin which is a target substance was obtained. This reaction scheme is shown in FIG. Further, FIG. 5 shows a ¹ H-NMR (300 MHz) spectrum of maleimide phenylporphyrin. In addition, the dimethyl sulfoxide purchased from MERK company was used for the deuterated solvent for NMR. It was confirmed that the target substance was obtained. In the above synthesis, dichloromethane was used as a solvent, but it could also be synthesized using acetic acid or chloroform. However, dichloromethane is preferably used from the viewpoint of yield.

[Preparation of fluorescent film (maleimide porphyrin film)]
The fluorescent film used in the mercapto group-containing substance detection device was produced as follows. After adding polystyrene to acetonitrile, it was slowly stirred to prepare a polystyrene solution. To this polystyrene solution, the ethanol solution of maleimide porphyrin synthesized above was added and stirred slowly. Air was prevented from entering at this time. This was coated on a slide glass and then naturally dried to obtain a fluorescent film made of maleimide porphyrin.

[Preparation of sample gas]
The sample gas was prepared as follows. Mercaptoethanol (molecular weight 78, specific gravity 1.114), which is a mercapto group-containing substance, was dissolved in ethanol to a volume ratio of 0.1% to prepare a mercaptoethanol solution. Next, 1 μL of a mercaptoethanol solution was dropped with a microsyringe into a fluororesin odor collection bag (10 L), and then inflated to about 9 L using odorless air. Waiting for all of the mercaptoethanol solution to evaporate, odorless air was added to make the whole 10 L. The temperature was 25 ° C. Since the number of moles = pressure × volume / (gas constant × absolute temperature), the total number of moles of gas in the odor collection bag is 1 × 10 / (0.0821 × (273.15 + 25) = 0.41 mole. On the other hand, the number of moles of mercaptoethanol is 0.001 × 0.001 × 1.114 / 78 = 1.4 × 10 ⁻⁸ mol, so the mercaptoethanol concentration in this sample gas is 1 4 × 10 ⁻⁸ /0.41×10 ⁹ = 35 ppb This sample gas and odorless air are appropriately mixed by an air pump to obtain seven values of 0, 1, 2, 5, 10, 20, and 35 ppb. A sample gas was obtained.

[Mercapto group-containing substance detection experiment using mercapto group-containing substance detector]
The sample gas prepared above was detected using a mercapto group-containing substance detector (light source: blue light-emitting diode capable of emitting blue light having a center wavelength of 430 nm) having the same configuration as that shown in FIG. The relationship between the mercaptoethanol concentration and the response amount (voltage) at this time is shown in FIG. Although it responds even when the mercaptoethanol concentration is 0, this is considered to be due to excitation light transmitted through the optical filter and fluorescence from unreacted maleimide porphyrin. The cause of the former is that the optical filter did not completely block blue light and that the light source emits light having a longer wavelength than blue although the amount is small. The reason for the latter is that the fluorescence quenching of porphyrin by the maleimide group is incomplete. However, for very dilute mercaptoethanol, a linear relationship was obtained between concentration and response. That is, by using the mercapto group-containing substance detector according to the present invention, the concentration of a mercapto group-containing substance in the sample gas could be detected with high sensitivity. There was no response to ethanol.

  In this example, mercaptoethanol was used as the mercapto group-containing substance. However, even if hydrogen sulfide (which is one in which hydrogen is added to a mercapto group), which is said to be one of the four major life malodor substances, is used, the fluorescence intensity is high. Because of the increase, hydrogen sulfide can be detected. As hydrogen sulfide, dilute hydrochloric acid was added to 100 mg of iron (II) sulfide, and the generated hydrogen sulfide was collected by water replacement.

  Further, it is presumed that the same effect can be obtained with methyl mercaptan (which is a product obtained by adding a methyl group to a mercapto group) or other substances. In fact, even when put in the same container as the rotten food (raw saury, grilled saury, fresh cabbage, grilled cabbage, fresh cucumber, raw beef, grilled beef, rice, etc.), it fluoresced. It is thought that methyl mercaptan and hydrogen sulfide were generated from these spoiled foods.

  The maleimide porphyrin used in this example contains zinc as a porphyrin central metal. However, when maleimide porphyrin obtained by treating maleimide porphyrin with sulfuric acid or the like to remove zinc is used, the fluorescence intensity increases and the sensitivity is improved. It is estimated that there is. However, maleimide porphyrin from which zinc has been removed is presumed to be less stable because the probability of degradation increases.

Moreover, although the present Example showed about the maleimide porphyrin in which three maleimide groups were introduce | transduced, it is convinced that the same effect is acquired also in the case of 1, 2 or 4 pieces. In addition, a compound in which the maleimide group is bonded to the porphyrin skeleton through one phenyl group is shown, but a compound in which the maleimide group is bonded to two or three phenyl groups, or the maleimide group is bonded to the porphyrin skeleton. We are convinced that the same effect can be obtained in the case of a directly bonded compound. In this example, the maleimide group is added to the para position of the phenyl group bonded to the porphyrin skeleton. In this case, as described above, unreacted maleimidoporphyrin also emits a slight fluorescence, but by adding it to the meta or ortho position of the phenyl group, the fluorescence intensity of unreacted maleimidoporphyrin could be reduced. Furthermore, it is convinced that the same effect can be obtained in the case where about 1 to 4 methylene groups (—CH ₂ —) are linked in place of the phenyl group, or in the case of other functional atomic groups. .

In this example, maleimide porphyrin was used as the fluorescent material, but it has been confirmed that similar effects can be obtained even when maleimide pyrene or maleimide coumarin is used. For example, 7-dimethylamino-3- (4′-maleimidoylphenyl) -4-methylcoumarin as maleimidocoumarin was dissolved in dimethylsulfoxide to obtain a fluorescent substance solution. A fluorescent substance solution was dropped on a high purity filter paper or a glass-coated silica substrate to prepare a fluorescent substance solution holding part. Instead of the reaction part and the substrate of the mercapto group-containing substance detection apparatus shown in FIG. 1, a fluorescent substance solution holding part was arranged in the reaction cell. Using this mercapto group-containing substance detection device (light source: light-emitting diode capable of irradiating light in the wavelength range of 380 to 420 nm), sample gas was detected in the same manner as maleimide porphyrin. Fluorescence was detected. Even when the light source was changed to a light emitting diode capable of emitting light in the wavelength range of 360 to 380 nm, blue fluorescence was detected in the same manner as described above. Further, instead of introducing the sample gas, the fluorescence was detected even if the sample gas was put in the same container as the spoiled food. However, when the fluorescent substance solution was dried and the same operation was performed, the detection sensitivity of blue fluorescence decreased. This is presumably because the fact that the fluorescent material is in a free state in the hardly volatile organic solution contributes to an increase in the transportation speed with respect to the mercapto group-containing material and an increase in the fluorescence yield. Unlike maleimide porphyrin, maleimidocoumarin needs to use ultraviolet light as an excitation light source, which increases costs.
In the case of maleimidopyrene, since the excitation wavelength is ultraviolet light of about 340 nm, a light emitting diode cannot be used as a light source. For this purpose, it is necessary to use an ultraviolet lamp, which can naturally be used in the future when a light emitting diode emitting ultraviolet light of this wavelength is developed. It is necessary to use an optical filter that transmits the fluorescence emitted from the fluorescent material.
In addition, even if it is another fluorescent functional group, the same effect can be expected by introducing a maleimide group.

Further, in this example, a maleimide porphyrin membrane obtained by applying an ethanol solution of maleimide porphyrin on a slide glass and drying was used. However, a maleimide porphyrin membrane prepared by the following methods (1) and (2) But similar results were obtained.
(1) An ethanol solution of maleimide porphyrin is dropped onto a glass substrate coated with silica gel and dried to obtain a fluorescent film made of maleimide porphyrin.
(2) A pure aluminum substrate and a platinum substrate are immersed in a sulfuric acid aqueous solution, and the aluminum substrate is applied with a positive potential and a negative potential is applied to the platinum substrate with a DC power source. Then, the aluminum substrate gradually becomes cloudy. In this state, it is washed with distilled water and dried. An ethanol solution of maleimide porphyrin is added dropwise thereto and dried to obtain a maleimide porphyrin film.

<Example 2>
An experiment similar to that of Example 1 was performed using a mercapto group-containing substance detection device having the same configuration as that shown in FIG. The amount of response (voltage) at this time was 10 times greater than that in Example 1. However, the response amount in the case of not containing mercaptoethanol was also four times or more. This is because the optical filter cannot completely remove the excitation light from the light source. However, the so-called S / N ratio improved by 2.5 times. Thus, the optical filter does not need to completely block the excitation light from the light source.

It is a figure for demonstrating the structure of the mercapto group containing material detection apparatus by Embodiment 1 of this invention. It is a figure for demonstrating the structure of the mercapto group containing substance detection apparatus by Embodiment 2 of this invention. It is a figure for demonstrating the modification of the mercapto group containing substance detection apparatus by Embodiment 2 of this invention. 2 is a synthesis scheme of maleimide porphyrin used in Example 1. FIG. 2 is an NMR spectrum of maleimide porphyrin used in Example 1. 2 is a graph showing the relationship between the concentration of mercaptoethanol and voltage in Example 1. FIG.

Explanation of symbols

  DESCRIPTION OF SYMBOLS 1 Reaction part, 2 Light source, 3 Fluorescence detection part, 4 Optical filter, 5 Calculation part, 6 Substrate, 7 Sample gas introduction pipe, 8 Sample gas discharge pipe, 9 Reaction cell, 10 Light receiving element, 11 Photodetection circuit board, 12 Hole, 13 O-ring.

Claims (5)

The fluorescent substance and the mercapto group-containing substance react with each other , including a fluorescent substance whose fluorescence yield increases when the maleimide group is bonded to the fluorescent functional group directly or through another functional group and reacts with the mercapto group-containing substance. A reaction part
A light source that irradiates a reaction product of a fluorescent substance and a mercapto group-containing substance with excitation light;
A fluorescence detector that receives fluorescence emitted from the reaction product and outputs an electrical signal corresponding to the fluorescence intensity ;
A Rume mercapto group-containing substance detection apparatus comprising a <br/> a calculation unit for calculating the concentration of the mercapto group-containing material based on an electric signal output from the fluorescence detection unit,
The fluorescent material has the following formula:

A mercapto group-containing substance detection device represented by: The mercapto according to claim 1 , wherein the reaction unit includes a fluorescent material solution holding unit in which a fluorescent material solution obtained by dissolving or suspending the fluorescent material in a hardly volatile organic solvent is held on a support. Group-containing substance detection device. 3. The mercapto group-containing substance detection according to claim 1, further comprising an optical filter that is disposed between the reaction unit and the fluorescence detection unit and selectively transmits fluorescence emitted from a reaction product. apparatus. The reaction part is made of a fluorescent film containing the fluorescent substance, the fluorescence detection part is made of a light receiving element and a light detection circuit board, and the reaction part made of the optical filter and the fluorescent film is formed on the light receiving surface of the light receiving element. The mercapto group-containing substance detection device according to claim 3 , wherein the mercapto group-containing substance detection device is laminated in order. Fluorescent substance whose maleimide group is bonded to the fluorescent functional group directly or via other functional atomic group and reacts with the mercapto group-containing substance to increase the fluorescence yield, and the mercapto group-containing substance are reacted, and the reaction A method for detecting a mercapto group-containing substance by measuring a fluorescence intensity when the product is excited and obtaining a concentration of the mercapto group-containing substance based on the measured fluorescence intensity ,
The fluorescent material has the following formula:

A method for detecting a mercapto group-containing substance, characterized by:

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