Bimodal multi-response fluorescent probe and application thereof

Abstract

The invention relates to a bimodal multi-response fluorescent probe and application thereof, the fluorescent probe has a structural general formula as shown in formula (I): # imgabs0 #, in the formula (I), Ar1 is a conjugated aromatic ring group, and R1 is a substituent group at any position in Ar1; ar2 is a conjugated aromatic ring group, R2 is a substituent group at any position in Ar2, and R2 is a maleimide derivative group. In the molecular structure of the fluorescent probe provided by the invention, R2 is a maleimide derivative group, and the maleimide derivative group can be reacted and combined with sulfydryl in amino acid, so that the fluorescent probe molecule can be endowed with the ability of targeting reaction of amino acid, protein and polypeptide chemical substances on the surface of various latent fingerprint traces; therefore, the purpose of detecting various latent fingerprints by using the fluorescent probe is achieved.

Description

Technical Field

[0001] The present application relates to the technical field of fluorescent probes, and in particular to a dual-modal multi-response fluorescent probe and its application. Background Art

[0002] Fingerprints are different for each individual and will not change throughout life. Therefore, fingerprints often play an important role in forensic science and criminal investigation. Most of the fingerprints at the crime scene are latent fingerprints, which cannot be directly observed by the human eye. Therefore, many means and methods of latent fingerprint detection and imaging provide great convenience for evidence collectors. Latent fingerprints are divided into sweat latent fingerprints and blood latent fingerprints. Sweat latent fingerprints refer to the sweat or other liquids secreted by the human body that are stained by human fingers in daily production and life. Then the sweat latent fingerprints are left by the contact between the fingers and the relevant objects. Blood latent fingerprints refer to the latent traces produced by the contact between the fingers and the relevant objects after being stained with blood. After a period of aging or artificial washing, the human eye is usually unable to intuitively judge whether the latent fingerprint exists or not, what its detailed characteristics are, etc. Therefore, some latent fingerprint detection or imaging methods are needed to help people observe latent fingerprints (including blood latent fingerprints and sweat latent fingerprints) more intuitively.

[0003] The chemical substances on the surface of sweat latent fingerprint traces are analyzed based on the main body fluids secreted by the human body, and mainly include lipids, amino acids, peptides, sodium chloride, lysozyme, glucose, urea, etc. The chemical substances on the surface of blood latent fingerprint traces are basically the same as the main components of blood, mainly including: protein, electrolytes, and glucose, etc. Therefore, there are a certain amount of protein and amino acids on the surface of both types of latent fingerprint traces. The existing latent fingerprint detection method based on aggregation-induced luminescence has many defects, such as (1) it can only detect a single type of latent fingerprint trace; (2) it can only make the latent fingerprint emit fluorescence under specific excitation light; (3) the operation is cumbersome, etc. Summary of the invention

[0004] The present application provides a dual-modal multi-response fluorescent probe and its application to solve the following technical problem: how to realize fluorescent probe detection of multiple latent fingerprints.

[0005] In a first aspect, the present application provides a dual-modal multi-response fluorescent probe, wherein the fluorescent probe has a general structural formula as shown in formula (1):

[0006]

[0007] In formula (1), Ar1 is a conjugated aromatic ring group, and R1 is a substituent at any position of Ar1; Ar2 is a conjugated aromatic ring group, and R2 is a substituent at any position of Ar2, and R2 is a maleimide derivative group.

[0008] Optionally, R2 includes one of the following:

[0009]

[0010] Optionally, Ar2 includes one of the following:

[0011]

[0012] Optionally, the R1 includes one of the following:

[0013] Hydrogen, chlorine, bromine, iodine, nitro, cyano, carboxyl, hydroxyl, ester, alkyl, amino-terminal alkyl, hydroxy-terminal alkyl, water-soluble group.

[0014] Optionally, Ar1 includes one of the following:

[0015]

[0016] In a second aspect, the present application provides an application of the fluorescent probe described in any one of claims 1 to 5 of the first aspect in fingerprint trace detection imaging.

[0017] Optionally, the application includes the following steps:

[0018] A solution containing a fluorescent probe is brought into contact with a latent fingerprint trace, and under the action of light excitation, the latent fingerprint trace is specifically marked to achieve fluorescent imaging of the latent fingerprint.

[0019] Optionally, the concentration of the fluorescent probe in the solution containing the fluorescent probe is 5 μmol / L to 100 μmol / L.

[0020] Optionally, the lighting includes one of the following: visible blue light, white light, and natural light.

[0021] Optionally, the latent fingerprint includes one of the following: sweat latent fingerprint and blood latent fingerprint.

[0022] The above technical solution provided by the embodiment of the present application has the following advantages compared with the prior art:

[0023] The fluorescent probe provided in the embodiment of the present application has a cyano group connected to one end of the double bond in its molecular structure. The cyano group can enhance the conjugated structure in the fluorescent probe and enhance the push-pull electron effect within the molecular structure of the fluorescent probe, thereby being beneficial to the stability of the fluorescence emission and the red shift of the fluorescence emission band to a certain extent; the conjugated aromatic ring groups Ar1 and Ar2 connected to both ends of the double bond can ensure the aggregation-induced luminescence effect of the probe molecule and enhance the push-pull electron effect, which is beneficial to the enhancement of fluorescence emission and the red shift of the emission band; R2 is a maleimide derivative group, which can react and combine with the thiol group in some amino acids in the human body, thereby giving the fluorescent probe molecule the ability to target the amino acids, proteins, and polypeptide chemicals on the surface of various latent fingerprint traces, thereby achieving the purpose of detecting various latent fingerprints with the fluorescent probe. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the present application and, together with the description, serve to explain the principles of the present application.

[0025] In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, for ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative labor.

[0026] Figure 1 This is a sweat latent fingerprint staining imaging image of a fluorescent probe provided in Example 1 of the present application on a stainless steel background;

[0027] Figure 2 This is a blood latent fingerprint staining imaging image of a fluorescent probe provided in Example 1 of the present application on a stainless steel background;

[0028] Figure 3 This is a sweat latent fingerprint staining imaging image of a fluorescent probe provided in Example 2 of the present application on a stainless steel background;

[0029] Figure 4 This is a blood latent fingerprint staining imaging image of a fluorescent probe provided in Example 2 of the present application on a stainless steel background;

[0030] Figure 5 This is a sweat latent fingerprint staining imaging image of a fluorescent probe provided in Example 3 of the present application on a stainless steel background;

[0031] Figure 6 This is a blood latent fingerprint staining imaging image of a fluorescent probe provided in Example 3 of the present application on a stainless steel background. DETAILED DESCRIPTION

[0032] In order to make the purpose, technical solution and advantages of the embodiments of the present application clearer, the technical solution in the embodiments of the present application will be clearly and completely described below in conjunction with the drawings in the embodiments of the present application. Obviously, the described embodiments are part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of this application.

[0033] Various embodiments of the present application may be presented in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be understood as a rigid limitation on the scope of the present application; therefore, the range description should be considered to have specifically disclosed all possible sub-ranges and single numerical values ​​within the range. For example, the range description from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which apply regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fractional or integer) within the indicated range.

[0034] In this application, unless otherwise specified, directional words such as "upper" and "lower" used refer specifically to the directions of the drawings in the accompanying drawings. In addition, in the description of the specification of this application, the terms "include", "comprise", etc. mean "including but not limited to".

[0035] Unless otherwise specified, various raw materials, reagents, instruments and equipment used in this application can be purchased from the market or prepared by existing methods.

[0036] In a first aspect, the present application provides a dual-modal multi-response fluorescent probe, wherein the fluorescent probe has a general structural formula as shown in formula (1):

[0037]

[0038] In formula (1), Ar1 is a conjugated aromatic ring group, and R1 is a substituent at any position of Ar1; Ar2 is a conjugated aromatic ring group, and R2 is a substituent at any position of Ar2, and R2 is a maleimide derivative group.

[0039] In the embodiment of the present application, in the molecular structure of the fluorescent probe, a cyano group is connected to one end of the double bond, and the cyano group can enhance the conjugated structure in the fluorescent probe, as well as the push-pull electron effect within the molecular structure of the fluorescent probe, thereby being beneficial to the stability of the fluorescence emission and the red shift of the fluorescence emission band to a certain extent; the conjugated aromatic ring groups Ar1 and Ar2 connected to both ends of the double bond can ensure the aggregation-induced emission effect of the probe molecule, as well as enhance the push-pull electron effect, which is beneficial to the enhancement of fluorescence emission and the red shift of the emission band; the Ar1-R1 structure can mainly provide a hydrophobic effect, targeting lipid substances in latent fingerprint traces; R2 is a maleimide derivative group, which can react and combine with the thiol group in the amino acid, thereby giving the fluorescent probe molecule the ability to target the amino acids, proteins, and polypeptide chemicals on the surface of various latent fingerprint traces, thereby achieving the purpose of using fluorescent probes to detect various latent fingerprints.

[0040] In some embodiments, R2 comprises one of the following:

[0041]

[0042] In the embodiment of the present application, the above-mentioned R2 substituent is a maleimide derivative group, which can react and combine with the sulfhydryl group in the amino acid, thereby giving the probe molecule the ability to target and react to amino acids, proteins and polypeptide chemicals on the surface of blood latent fingerprints and sweat latent fingerprints.

[0043] In some embodiments, the Ar2 comprises one of the following:

[0044]

[0045] In the embodiment of the present application, the above-mentioned Ar2 can be a heteroaromatic ring structure, which is beneficial to further control the electronic properties of the probe molecule and the intensity and wavelength of the fluorescence emission.

[0046] In some embodiments, the R1 comprises one of the following:

[0047] Hydrogen, chlorine, bromine, iodine, nitro, cyano, carboxyl, hydroxyl, ester, alkyl, amino-terminal alkyl, hydroxy-terminal alkyl, water-soluble group.

[0048] In the embodiment of the present application, R1 can be one of hydrogen, chlorine, bromine, iodine, nitro, cyano, carboxyl, hydroxyl, ester, alkyl, amino-terminated alkyl, hydroxy-terminated alkyl, and water-soluble groups; wherein the water-soluble group can be one of the following:

[0049]

[0050] The water-soluble group R1 can enhance the water solubility of the fluorescent probe, dissolve it in a solvent with a higher polarity, and increase its shelf life in the developer solvent.

[0051] In some embodiments, the Ar1 comprises one of the following:

[0052]

[0053] In the embodiment of the present application, the above-mentioned Ar1 can be a larger multi-rotor structure similar to triphenylamine or a larger heteroaromatic ring structure, which can give the probe the property of aggregation-induced emission, while enhancing the intramolecular push-pull electron effect and the red shift of the fluorescence emission wavelength.

[0054] In a second aspect, the present application provides an application of the fluorescent probe described in any one of claims 1 to 5 of the first aspect in fingerprint trace detection imaging.

[0055] In some embodiments, the application comprises the following steps:

[0056] A solution containing a fluorescent probe is brought into contact with a latent fingerprint trace, and under the action of light excitation, the latent fingerprint trace is specifically marked to achieve fluorescent imaging of the latent fingerprint.

[0057] In the embodiment of the present application, the solution containing the fluorescent probe is in contact with the latent fingerprint trace, and under the irradiation of the excitation light, the latent fingerprint trace is made to emit strong fluorescence, and then the latent fingerprint trace can be fixed using a photographing device. In addition, after the fluorescent probe is gathered at the ridge of the latent fingerprint, the excess fluorescent probe solution can be removed.

[0058] In some embodiments, the concentration of the fluorescent probe in the solution containing the fluorescent probe is 5 μmol / L to 100 μmol / L.

[0059] In an embodiment of the present application, the concentration of the fluorescent probe in the solution containing the fluorescent probe can be 5 μmol / L to 100 μmol / L, which can be conducive to the appropriate concentration of the aggregation-induced emission effect, and this concentration reduces the background fluorescence while ensuring good imaging effects, saving raw materials. Exemplarily, the concentration of the fluorescent probe in the solution containing the fluorescent probe can be 5 μmol / L, 10 μmol / L, 15 μmol / L, 20 μmol / L, 25 μmol / L, 30 μmol / L, 35 μmol / L, 40 μmol / L, 45 μmol / L, 50 μmol / L, 100 μmol / L, etc.

[0060] In some embodiments, the illumination comprises one of the following: visible blue light, white light, and natural light.

[0061] In the embodiment of the present application, the latent fingerprint traces can still show red traces under the illumination of visible blue light, white light and natural light, and the wavelength of the above visible blue light is 450 nanometers to 560 nanometers.

[0062] In some embodiments, the latent fingerprint includes one of the following: sweat latent fingerprint, blood latent fingerprint.

[0063] In the embodiment of the present application, the fluorescent probe is a probe molecule that can perform targeted response to multiple latent fingerprint traces (blood latent fingerprints and sweat latent fingerprints) in multiple modes of visible blue light, white light, and natural light. Therefore, the fluorescent probe can simultaneously meet the needs of detecting sweat latent fingerprints and blood latent fingerprints, and can show red fluorescence under blue light excitation, and also has red traces under natural white light irradiation, thereby solving the defects of the existing method of single detection target, limited conditions for excitation and manifestation, and complex operation.

[0064] The application of the dual-modal multi-responsive fluorescent probe in fingerprint fluorescence imaging is realized based on the above-mentioned fluorescent probe. The specific molecular structure of the dual-modal multi-responsive fluorescent probe can refer to the above-mentioned embodiment. Since the application of the dual-modal multi-responsive fluorescent probe in fingerprint fluorescence imaging adopts part or all of the technical solutions of the above-mentioned embodiments, it has at least all the beneficial effects brought by the technical solutions of the above-mentioned embodiments, which will not be described one by one here.

[0065] In summary, the fluorescent probe provided in the embodiment of the present application has a group for amino acid targeted reaction binding and a structure for lipid physical adsorption binding due to the particularity of its structure, so it can simultaneously detect and image blood latent fingerprints and sweat latent fingerprints; the fluorescent probe provided in the embodiment of the present application has a good property of aggregation-induced luminescence due to its special molecular structure; using the fluorescent probe provided in the embodiment of the present application, with the help of an ordinary SLR camera, the latent fingerprint on the surface of a smooth object can be immersed in the fluorescent probe solution, and then the traces and related detailed features of the latent fingerprint can be observed under the excitation irradiation of blue light or natural white light; the fluorescent probe molecule provided in the embodiment of the present application emits red fluorescence, has strong penetrating ability, and its red traces can also be identified by the naked eye under natural white light, simplifying the latent fingerprint imaging step.

[0066] The present application will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are intended only to illustrate the present application and are not intended to limit the scope of the present application. The experimental methods for which specific conditions are not specified in the following examples are usually measured according to national standards. If there is no corresponding national standard, then the conditions recommended by the manufacturer are followed.

[0067] Example 1

[0068] The molecular structure of a dual-modal multi-response fluorescent probe is shown in formula (1):

[0069]

[0070] In formula (1), Ar1 is R1 is H; Ar2 is R2 is

[0071] A method for preparing a dual-modal multi-response fluorescent probe, comprising:

[0072] 4-(Diphenylamino)benzaldehyde (1 eq) and 4-(isocyanomethyl)pyridine (1 eq) were added to the reaction flask, and ethanol was added as the reaction solvent. A magnetic bar was placed in the flask, and the temperature was raised to 80°C. The reaction was stirred evenly and heated for about 24 hours. The final product was generated, and finally purified by column chromatography to obtain compound 1.

[0073] Compound 1 (1 eq) and 1-(2-bromoethyl)-1H-pyrrole-2,5-dione (1 eq) were added to the reaction bottle. DMF was added as the reaction solvent, a magnetic bar was placed, the temperature was raised to 120°C, and the reaction was stirred evenly for about 6 hours. The probe molecule was generated and purified by column chromatography to obtain a dual-modal multi-responsive fluorescent probe.

[0074] Application of the dual-modal multi-response fluorescent probe prepared in Example 1

[0075] (1) Using the fluorescent probe of Example 1, a solution containing the fluorescent probe at 50 μmol / L was prepared. The solution containing the fluorescent probe was used to stain the latent fingerprint traces on the surface of the stainless steel substrate. Under blue light irradiation, the latent fingerprint traces emitted red fluorescence, which was photographed using a SLR camera.

[0076] (2) Using the fluorescent probe of Example 1, a solution containing the fluorescent probe was prepared at 50 μmol / L. The solution containing the fluorescent probe was used to stain the blood latent fingerprint traces on the surface of the stainless steel substrate. Under the irradiation of natural white light, red traces were produced at the latent fingerprint traces, which were photographed and fixed using a SLR camera.

[0077] Example 2

[0078] The molecular structure of a dual-modal multi-response fluorescent probe is shown in formula (1):

[0079]

[0080] In formula (1), Ar1 is R1 is H; Ar2 is R2 is

[0082] A method for preparing a dual-modal multi-response fluorescent probe, comprising:

[0083] 4-(Diphenylamino)benzaldehyde (1eq), 4-(isocyanomethyl)quinoline (1eq) were added to the reaction flask, and ethanol was added as the reaction solvent. A magnetic bar was placed in the flask, and the temperature was raised to 80°C. The reaction was stirred evenly and heated for about 24 hours. The final product was generated, and finally purified by column chromatography to obtain compound 1.

[0084] Compound 1 (1 eq) and 1-(2-bromoethyl)-1H-pyrrole-2,5-dione (1 eq) were added to the reaction bottle. DMF was added as the reaction solvent, a magnetic bar was placed, the temperature was raised to 120°C, and the reaction was stirred evenly for about 6 hours. The probe molecule was generated and purified by column chromatography to obtain a dual-modal multi-responsive fluorescent probe.

[0085] Example 2 Application of the prepared dual-modal multi-response fluorescent probe

[0086] (1) Using the fluorescent probe of Example 2, a solution containing the fluorescent probe was prepared at 50 μmol / L. The solution containing the fluorescent probe was used to stain the latent fingerprint traces on the surface of the stainless steel substrate. The latent fingerprint traces emitted red fluorescence under blue light irradiation, and a single-lens reflex camera was used to photograph them.

[0087] (2) Using the fluorescent probe of Example 2, a solution containing the fluorescent probe was prepared at 50 μmol / L. The solution containing the fluorescent probe was used to stain the blood latent fingerprint traces on the surface of the stainless steel substrate. Under natural white light, red traces were produced at the latent fingerprint traces, which were photographed and fixed using a SLR camera.

[0088] Example 3

[0089] The molecular structure of a dual-modal multi-response fluorescent probe is shown in formula (1):

[0090]

[0091] In formula (1), Ar1 is R1 is H; Ar2 is R2 is

[0092] A method for preparing a dual-modal multi-response fluorescent probe, comprising:

[0093] 4-(9H-carbazole-9-yl)benzaldehyde (1eq), 4-(isocyanomethyl)pyridine (1eq) were added to the reaction bottle, and ethanol was added as the reaction solvent. A magnetic bar was placed in the reaction bottle, and the temperature was raised to 80°C. The reaction was stirred evenly and heated for about 24 hours. The final product was generated and purified by column chromatography to obtain compound 1.

[0094] Compound 1 (1 eq) and 1-(2-bromoethyl)-1H-pyrrole-2,5-dione (1 eq) were added to the reaction bottle. DMF was added as the reaction solvent, a magnetic bar was placed, the temperature was raised to 120°C, and the reaction was stirred evenly for about 6 hours. The probe molecule was generated and purified by column chromatography to obtain a dual-modal multi-responsive fluorescent probe.

[0095] Example 3 Application of the prepared dual-modal multi-response fluorescent probe

[0096] (1) Using the fluorescent probe of Example 3, a solution containing the fluorescent probe was prepared at 50 μmol / L. The solution containing the fluorescent probe was used to stain the sweat latent fingerprint traces on the surface of the stainless steel substrate. Under blue light irradiation, the latent fingerprint traces emitted red fluorescence, which was photographed using a SLR camera.

[0097] (2) Using the fluorescent probe of Example 3, a solution containing the fluorescent probe was prepared at 50 μmol / L. The solution containing the fluorescent probe was used to stain the blood latent fingerprint traces on the surface of the stainless steel substrate. Under natural white light, red traces were produced at the latent fingerprint traces, which were photographed and fixed using a SLR camera.

[0098] Result analysis:

[0099] Figure 1 This is a latent fingerprint staining imaging image of a fluorescent probe provided in Example 1 of the present application on a stainless steel background; see Figure 1 After the sweat latent fingerprint is stained with the solution of the probe molecule provided in the embodiment of the present application, it will emit red fluorescence under the excitation of blue light. Based on the structural particularity of the probe molecule shown in the embodiment of the present application, the probe molecule in the solution will be physically adsorbed to the lipids on the surface of the sweat latent fingerprint trace, and will react and combine with the sulfhydryl groups in the surface amino acid substances. The two effects occur simultaneously, so that the probe molecule emits red fluorescence on the surface of the latent fingerprint trace based on the principle of aggregation and luminescence, thereby successfully detecting the sweat latent fingerprint trace.

[0100] Figure 2 This is a latent fingerprint staining imaging image of a fluorescent probe provided in Example 1 of the present application on a stainless steel background; see Figure 2 There are many amino acids on the surface of the latent fingerprint traces. The probe molecules provided in the embodiments of the present application will react and combine with the thiol groups in the amino acids on the surface of the latent fingerprint traces. Based on the principle of aggregation-induced luminescence, fluorescence is emitted on the surface of the latent fingerprint traces. In addition, under the irradiation of natural white light, there will also be red traces of the probe molecules on the latent fingerprints after being stained with the solution, further truly restoring the original appearance of the latent fingerprints.

[0101] Figure 3This is a staining image of a latent fingerprint of sweat on a stainless steel background using a fluorescent probe provided in Example 2 of the present application; it shows that the fluorescent probe synthesized in Example 2 can combine with lipid substances in latent fingerprint traces through physical adsorption and other effects, induce the aggregation state of the probe molecules, and illuminate the latent fingerprint of sweat based on the effect of aggregation-induced luminescence.

[0102] Figure 4 This is an imaging diagram of a blood latent fingerprint staining on a stainless steel background using a fluorescent probe provided in Example 2 of the present application; it indicates that the fluorescent probe synthesized in Example 2 can combine with free thiol-containing amino acids and polypeptides such as cysteine ​​in the blood latent fingerprint traces through chemical reactions, thereby inducing an aggregation state, emitting fluorescence based on the aggregation-induced luminescence effect, and ultimately lighting up the blood latent fingerprint.

[0103] Figure 5 This is a staining image of a latent fingerprint of sweat on a stainless steel background using a fluorescent probe provided in Example 3 of the present application; it shows that the fluorescent probe synthesized in Example 3 can combine with lipid substances in latent fingerprint traces through physical adsorption and other effects, induce the aggregation state of the probe molecules, and illuminate the latent fingerprint of sweat based on the effect of aggregation-induced luminescence.

[0104] Figure 6 This is a staining image of a blood latent fingerprint provided by a fluorescent probe in Example 3 of the present application on a stainless steel background. It shows that the fluorescent probe synthesized in Example 3 can combine with amino acids and polypeptides containing free sulfhydryl groups such as cysteine ​​in the blood latent fingerprint traces through chemical reactions, thereby inducing aggregation, emitting fluorescence based on the aggregation-induced luminescence effect, and finally lighting up the blood latent fingerprint.

[0105] One or more technical solutions in the embodiments of the present application also have at least the following technical effects or advantages:

[0106] (1) The dual-mode multi-response fluorescent probe provided in the embodiment of the present application can detect sweat latent fingerprints and blood latent fingerprints at the same time. This makes the operation steps of latent fingerprint trace detection simpler, and the result of multi-target trace response can greatly reduce the omission of trace detection and more comprehensively detect latent fingerprint traces;

[0107] (2) After the latent fingerprint is stained, it will emit red fluorescence under the excitation of blue light; at the same time, during the day, under the irradiation of natural white light, the surface of the latent fingerprint will also have red marks to help observe the latent fingerprint. Therefore, the double excitation latent fingerprint development method further simplifies the operation steps and greatly improves the convenience of latent fingerprint detection;

[0108] (3) In-situ latent fingerprint detection, development and imaging based on aggregation-induced luminescence effectively reduce the interference of background fluorescence and greatly improve the clarity and recognition of latent fingerprint imaging.

[0109] The above description is only a specific implementation of the present application, so that those skilled in the art can understand or implement the present application. Various modifications to these embodiments will be apparent to those skilled in the art, and the general principles defined herein can be implemented in other embodiments without departing from the spirit or scope of the present application. Therefore, the present application will not be limited to the embodiments shown herein, but will conform to the widest range consistent with the principles and novel features applied for herein.

Claims

1. A dual-modal multi-response fluorescent probe, characterized in that: The fluorescent probe has a general structural formula as shown in formula (1): In formula (1), Ar1 is a conjugated aromatic ring group, and R1 is a substituent at any position of Ar1; Ar2 is a conjugated aromatic ring group, and R2 is a substituent at any position of Ar2, and R2 is a maleimide derivative group.

2. The fluorescent probe according to claim 1, characterized in that R2 includes one of the following:

3. The fluorescent probe according to claim 1 or 2, characterized in that Ar2 includes one of the following:

4. The fluorescent probe according to claim 1, characterized in that The R1 includes the following: Hydrogen, chlorine, bromine, iodine, nitro, cyano, carboxyl, hydroxyl, ester, alkyl, amino-terminal alkyl, hydroxy-terminal alkyl, water-soluble group.

5. The fluorescent probe according to claim 1 or 4, characterized in that The Ar1 includes the following:

6. Use of the fluorescent probe according to any one of claims 1 to 5 in fingerprint trace detection imaging.

7. The use according to claim 6, characterized in that: The application comprises the following steps: A solution containing a fluorescent probe is brought into contact with a latent fingerprint trace, and under the action of light excitation, the latent fingerprint trace is specifically marked to achieve fluorescent imaging of the latent fingerprint.

8. The use according to claim 6, characterized in that: The concentration of the fluorescent probe in the solution containing the fluorescent probe is 5 μmol / L to 100 μmol / L.

9. The use according to claim 6, characterized in that: The illumination includes one of the following: visible blue light, white light, and natural light.

10. The use according to claim 6, characterized in that: The latent fingerprint includes the following: sweat latent fingerprint and blood latent fingerprint.

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