Alkenyl sulfone type fluorescent material as well as synthesis and application thereof

Abstract

The invention discloses an alkenyl sulfone type fluorescent material as well as synthesis and application thereof. The alkenyl sulfone type fluorescent material comprises a compound # imgabs0 # as shown in a formula I, and the material shows high brightness and stable fluorescence emission characteristics in a solid state and a liquid state. The method can be effectively applied to rapid visual detection of various aromatic explosives in an actual water sample.

Description

Technical Field

[0001] The present invention relates to the technical field of materials, and particularly relates to an alkenyl sulfone-based fluorescent material and its synthesis and application. Background Art

[0002] Dual-state emission (DSE) fluorescent molecules can emit light efficiently both in the aggregated state and in good solvents, overcoming the limitations of traditional fluorescent molecules. Their design is based on the donor-acceptor (D-A) structure. By adjusting the donor / acceptor strength or combining specific recognition sites, fluorescence regulation and selective detection are achieved, and they have broad application potential in the fields of fluorescence detection and bioimaging.

[0003] For example, related technologies have constructed a series of DSE molecular structural patterns of D-A molecules based on aurones as electron acceptors and common electron-donating groups; there are also related technologies that have constructed DSE molecules with a D-A structural pattern based on chalcone skeletons and pyrrolidinyl groups; or a series of AIE and DSE fluorescent molecules with a D-A structural pattern have been developed based on various benzoxazoles as electron acceptors and electron-rich aryl groups as electron donors.

[0004] Although a considerable number of electron acceptors (including benzoxazoles, mono / dicyanoethylenes, and BODIPYs, etc.) and various electron-withdrawing groups have been widely reported, strong acceptors used to reduce the HOMO-LUMO energy level are still limited.

[0005] Currently, among the reported sulfone-based fluorescent molecules, it is more common to link electron donors with a sulfone bridge or have a cyclic sulfone structure; however, their stability is still insufficient. Summary of the Invention

[0006] The present invention aims to at least solve one of the above technical problems in the prior art. To this end, the purpose of the present invention is to provide an alkenyl sulfone-based fluorescent material and its synthesis and application.

[0007] To achieve the above purpose, the technical solutions adopted by the present invention are as follows:

[0008] In the first aspect of the present invention, a compound of formula I is provided:

[0009]

[0010] Wherein, R 1 , R 2 are each independently selected from C 1 -C 4 alkyl, phenyl, or R 1 and R 2 together with the atoms to which they are attached form a 9- to 21-membered heteroaryl group; the heteroaryl group is unsubstituted or substituted by one or more C 1 -C4 Alkyl substitution;

[0011] R 3 Selected from C 1 ~C 4 alkyl, phenyl; the phenyl is unsubstituted or substituted by one or more C 1 ~C 4 alkyl.

[0012] In some embodiments of the present invention, the R 1 and R 2 and the atoms connected thereto form a group selected from carbazolyl indolyl dihydroindolyl dihydroacridinyl

[0013] In some embodiments of the present invention, the compound of formula I is selected from

[0014] The second aspect of the present invention provides a method for preparing a compound of formula I-1, comprising the following steps:

[0015]

[0016] Reacting a compound II of formula II with a compound III of formula III to obtain a compound of formula I-1

[0017] wherein X is a halogen (such as F, Cl, Br, I);

[0018] Y is selected from O, N, S;

[0019] R a , R b are each independently selected from hydrogen, C 1 ~C 4 alkyl, phenyl, or R 1 and R 2 and the atoms connected thereto form a 9-21 membered heteroaryl group; the heteroaryl group is unsubstituted or substituted by one or more C 1 ~C 4 alkyl;

[0020] and R a , R b are not both hydrogen at the same time; the definition of R 3 is as described above.

[0021] In some embodiments of the present invention, the compound of formula I-1 is selected from:

[0022] In some embodiments of the present invention, the reaction is a Suzuki-Miyaura coupling reaction; the catalysts used in the reaction include Pd(PPh 3 ) 2 Cl 2 、Pd(PPh 3 ) 4 、PdCl 2 (dppf), PdCl 2 、Pd(OAc) 2 、NiCl 2 (dppf), Ni(COD) 2 any one of them.

[0023] In some embodiments of the present invention, the reaction is carried out under alkaline conditions, and at least one of sodium carbonate, potassium carbonate, and cesium carbonate is used to adjust the reaction conditions to be alkaline; the temperature of the reaction is 30-90 °C, such as 40-70 °C; the reaction time is 6-12 h; the solvent used in the reaction includes a mixture of toluene and water in a volume ratio of (1-3):1.

[0024] The third aspect of the present invention provides a fluorescence sensing material including the compound of formula I-1.

[0025] The fourth aspect of the present invention provides a fluorescence detection device including the compound of formula I-1 or the fluorescence sensing material.

[0026] In some embodiments of the present invention, in the fluorescence detection device, the molar concentration of the compound of formula I-1 is 1 μM - 1 M, such as 1 μM - 0.1 M, 5 μM - 0.05 M, etc.

[0027] In some embodiments of the present invention, the fluorescence detection device includes a fluorescence detection test strip.

[0028] In some embodiments of the present invention, the compound of formula I-1 is loaded on the fluorescence detection test strip.

[0029] In some embodiments of the present invention, the loading amount of the compound of formula I-1 on the fluorescence detection test strip is 0.05 - 0.5 mg / cm 2 , such as 0.1 mg / cm 2 .

[0030] The fifth aspect of the present invention provides an application of the compound of formula I-1, or the fluorescence sensing material, or the fluorescence detection device in the detection of aromatic explosives.

[0031] The beneficial effects of the present invention are as follows:

[0032] (1) Using phenylacetylene and sodium sulfite as raw materials, the present invention generates an iodoalkenyl sulfone intermediate under the action of hydroiodic acid, and then reacts with arylboronic acid through Suzuki-Miyaura coupling reaction to synthesize a novel fluorescent sensing material in only two steps. This method avoids the high cost, complex steps and harsh conditions of traditional synthesis, uses inexpensive and easily available raw materials, and does not require expensive catalysts or special drugs and equipment. The reaction conditions are easy to control, the product purification is simple, the yield is as high as 80%, and the material structure is verified by 1 HNMR, 13 C NMR and HRMS and other analytical means.

[0033] (2) The alkenyl sulfone compounds in the specific embodiments of the present invention exhibit high brightness and stable fluorescence emission characteristics in both solid and liquid states.

[0034] (3) The dual-state emission fluorescent sensing material in the specific embodiments of the present invention can be effectively applied to the rapid visual detection of various aromatic explosives (NACs) in actual water samples. In addition, the material can be made into a portable test strip through a simple process to achieve rapid, highly sensitive and visual identification of explosives. Brief Description of the Drawings

[0035] Figure 1 It is the X-ray single crystal diffraction pattern of compound 3b in Example 1 of the present invention.

[0036] Figure 2 It is the X-ray single crystal diffraction pattern of compound 3d in Example 3 of the present invention.

[0037] Figure 3 It is the fluorescence emission spectrum of compound 3c in Example 5 of the present invention for different aromatic explosives.

[0038] Figure 4 It is the response time of compound 3c in Example 6 of the present invention to different aromatic explosives.

[0039] Figure 5 It is the visual detection result of the portable test strip loaded with compound 3c in Example 7 of the present invention for different aromatic explosives. Detailed Description of the Specific Embodiments

[0040] The content of the present invention will be further described in detail through specific embodiments below. The raw materials, reagents or devices used in the embodiments and comparative examples can be obtained from conventional commercial channels or can be obtained by existing technical methods without special instructions. Unless otherwise specified, the test or testing methods are conventional methods in the art.

[0041] Example 1

[0042] Compound 3b was prepared in this example The specific process is as follows:

[0043] In a 25 mL pressure-resistant tube, phenylacetylene (1.2 equiv.), sodium 4-toluenesulfinate (2.6 equiv.) and hydroiodic acid (2.4 equiv.) were added respectively, and then 5 mL of a mixed solvent of CH 3 CN:H 2 O = 1:1 (v / v) was added. The mixture was magnetically stirred at 70 °C for 6 h. After the reaction was completed, the reaction solution was quenched with an excessive amount of saturated aqueous sodium thiosulfate solution and extracted with dichloromethane (3 × 15 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain a crude product. Column chromatography separation (petroleum ether / ethyl acetate = 20 / 1, v / v) was carried out to obtain the pure intermediate iodoalkenyl sulfone compound 1a

[0044] In a 25 mL pressure-resistant tube, compound 1a (1.0 equiv.), N,N-dimethyl-4-boraniline (1.2 equiv.), potassium carbonate (1.2 equiv.), Pd(PPh 3 ) 2 Cl 2 (0.1 equiv.) and 3 mL of a mixed solvent of toluene:water = 2:1 (v / v) were added. After replacing the nitrogen to protect, the reaction was carried out at 60 °C for 8 h. After the reaction was completed, the reaction was quenched with an excessive amount of saturated ammonium chloride solution and extracted with dichloromethane (3 × 15 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain a crude product. Column chromatography separation (petroleum ether / ethyl acetate = 8 / 1, v / v) was carried out to obtain pure 3b, which is a pale yellowish-green solid with a yield of 81% and the melting point test result is m.p. = 111.9 - 113.0 °C

[0045] 1 H NMR (600 MHz, CDCl 3 ), δ, ppm: 2.34 (s, 3H, CH 3 -1), 2.95 (s, 6H, NCH 3 -22,23), 6.56 (d, J = 9.0 Hz, 2H, ArH-18,20), 6.88 (s, 1H, =CH-8), 7.02 (d, J = 9.0 Hz, 2H, ArH-17,21), 7.08 (m, 4H, ArH-3,4,12,14), 7.24 (d, J = 7.2 Hz, 2H, ArH-11,15), 7.32 (t, J = 7.2 Hz, 1H, ArH-13), 7.40 (d, J = 8.4 Hz, 2H, ArH-5,6);

[0046] 13 C NMR (150 MHz, CDCl 3 ), δ, ppm: 21.7 (C-1), 40.3 (C-22,23), 111.6 (C-8), 123.8 (C-13), 127.65 (C-18,20), 127.7 (C-3,4), 128.5 (C-11,15), 129.3 (C-17,21), 129.7 (C-12,14), 129.9 (C-5,6), 132.0 (C-16), 136.2 (C-2), 139.7 (C-7), 143.3 (C-10), 151.7 (C-9), 155.1 (C-19);

[0047] ESI-HRMS, m / z: Calcd for C 23 H 24 NO 2 S [M+H] + : 378.1522, Found: 378.1521.

[0048] X-ray single crystal diffraction pattern of compound 3b, as Figure 1 shown.

[0049] Example 2

[0050] Compound 3c was prepared in this example The specific procedure was as follows:

[0051] In a 25 mL pressure tube, compound 1a (1.0 equiv.), 4-borotriphenylamine (1.2 equiv.), potassium carbonate (1.2 equiv.), Pd(PPh 3 ) 2 Cl 2 (0.1 equiv.) and 3 mL of a mixed solvent of toluene:water = 2:1 (v / v) were added respectively. After replacing with nitrogen for protection, the reaction was carried out at 60 °C for 8 h. After the reaction was completed, the reaction was quenched by adding an excess of saturated ammonium chloride solution, and extracted with dichloromethane (3 × 15 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain a crude product. Column chromatography separation (petroleum ether / ethyl acetate = 8 / 1, v / v) gave the pure product 3c, which was a pale yellowish green solid with a yield of 75% and the melting point test result was m.p. = 125.8 - 127.1 °C.

[0052] 1 H NMR (600 MHz, CDCl 3 ), δ, ppm: 2.37 (s, 3H, CH 3-1), 6.88 (d, J = 9.0 Hz, 2H, ArH-18, 20), 6.95 (s, 1H, =CH-8), 7.03 (d, J = 9.0 Hz, 2H, ArH-23, 23'), 7.05 - 7.09 (m, 8H, ArH-24, 24', 25, 25', 26, 26', 27, 27'), 7.12 (d, J = 8.4 Hz, 2H, ArH-3, 4), 7.24 - 7.29 (m, 6H, ArH-11, 12, 14, 15, 17, 21), 7.33 - 7.36 (m, 1H, ArH-13), 7.43 (d, J = 8.4 Hz, 2H, ArH-5, 6);

[0053] 13 C NMR (150 MHz, CDCl 3 ), δ, ppm: 21.7 (C-1), 121.1 (C-18, 20), 124.3 (C-3, 4), 125.3 (C-8), 125.5 (C-23, 23', 27, 27'), 126.3 (C-13), 127.7 (C-25, 25'), 127.8 (C-17, 21), 129.2 (C-11, 15), 129.3 (C-12, 14), 129.6 (C-24, 24', 26, 26'), 128.8 (C-5, 6), 131.3 (C-16), 135.7 (C-2), 139.2 (C-7), 143.6 (C-10), 146.8 (C-22, 22'), 150.1 (C-19), 154.3 (C-9);

[0054] ESI-HRMS, m / z: Calcd for C 33 H 28 NO 2 S [M + H] + : 502.1835, Found: 502.1828.

[0055] Example 3

[0056] In this example, compound 3d was prepared The specific process was as follows:

[0057] In a 25 mL pressure tube, compound 1a (1.0 equiv.), 4-boronophenylcarbazole (1.2 equiv.), potassium carbonate (1.2 equiv.), Pd(PPh 3 ) 2 Cl 2(0.1 equiv.) and 3 mL of a toluene:water = 2:1 (v / v) mixed solvent. After replacing the nitrogen protection, the reaction was carried out at 60 °C for 8 h. After the reaction was completed, an excessive amount of saturated ammonium chloride solution was added to quench the reaction, and it was extracted with dichloromethane (3 × 15 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain the crude product. Column chromatography separation (petroleum ether / ethyl acetate = 8 / 1, v / v) gave the pure product 3d, which was a white solid with a yield of 78% and the melting point test result was m.p. = 181.1 - 181.8 °C.

[0058] 1 H NMR(600MHz,CDCl 3 ),δ,ppm:2.41(s,3H,CH 3 -1),7.12(s,1H,=CH-8),7.18 - 7.21(m,4H,ArH-11,15,25,25'),7.28 - 7.31(m,2H,ArH-24,24'),7.36 - 7.43(m,7H,ArH-12,13,14,17,18,20,21),7.45(d,J=8.4Hz,2H,ArH-3,4),7.51 - 7.55(m,4H,ArH-5,6,23,23'),8.13(d,J=7.8Hz,2H,ArH-26,26');

[0059] 13 C NMR(150MHz,CDCl 3 ),δ,ppm:21.7(C-1),109.8(C-23,23'),120.5(C-26,26'),120.6(C-25,25'),123.8(C-8),126.2(C-27,27'),126.8(C-26,26'),127.9(C-17,21),128.2(C-11,15),129.2(C-13),129.6(C-5,5,12,14),129.8(C-3,4),129.9(C-22,22'),135.4(C-16),137.9(C-19),139.8(C-2),140.5(C-7),135.4(C-9),144.0(C-10),153.7(C-9);

[0060] ESI-HRMS,m / z:Calcd for C 33 H 26 NO 2 S[M+H] + :500.1679,Found:500.1670.

[0061] The X-ray single crystal diffraction pattern of Compound 3d is as follows Figure 2 shown

[0062] Example 4

[0063] Compound 3e was prepared in this example The specific process is as follows

[0064] In a 25 mL pressure-resistant tube, phenylacetylene (1.2 equiv.), sodium ethanesulfinate (2.6 equiv.), and hydroiodic acid (2.4 equiv.) were added respectively, and then 5 mL of a mixed solvent of CH 3 CN:H 2 O = 1:1 (v / v) was added. The reaction was stirred magnetically at 70 °C for 6 h. After the reaction was completed, the reaction solution was quenched with an excessive amount of saturated sodium thiosulfate aqueous solution and extracted with dichloromethane (3 × 15 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain a crude product. Column chromatography separation (petroleum ether / ethyl acetate = 20 / 1, v / v) was carried out to obtain the pure intermediate iodoalkenyl sulfone compound 1b

[0065] In a 25 mL pressure-resistant tube, Compound 1b (1.0 equiv.), 4-borotriphenylamine (1.2 equiv.), potassium carbonate (1.2 equiv.), Pd(PPh 3 ) 2 Cl 2 (0.1 equiv.) and 3 mL of a mixed solvent of toluene:water = 2:1 (v / v) were added. After replacing the nitrogen to protect, the reaction was carried out at 60 °C for 8 h. After the reaction was completed, the reaction was quenched by adding an excessive amount of saturated ammonium chloride solution and extracted with dichloromethane (3 × 15 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain a crude product. Column chromatography separation (petroleum ether / ethyl acetate = 8 / 1, v / v) was carried out to obtain pure 3e, which is a white solid with a yield of 81% and the melting point test result is m.p. = 175.4 - 176.7 °C

[0066] 1 H NMR (600 MHz, CDCl 3 ), δ, ppm: 1.25 (t, J = 7.2 Hz, 3H, CH 3 -1), 2.68 (q, J = 7.2 Hz, 2H, CH 2-2), 6.68 (s, 1H, =CH-3), 6.93 (d, J=9.0 Hz, 2H, ArH-12, 13), 7.08 - 7.13 (m, 8H, ArH-14, 15, 18, 18', 20, 20', 22, 22'), 7.27 - 7.30 (m, 4H, ArH-19, 19', 21, 21'), 7.35 - 7.37 (m, 2H, ArH-7, 9), 7.42 - 7.44 (m, 3H, ArH-6, 8, 10);

[0067] 13 C NMR (150 MHz, CDCl 3 ), δ, ppm: 7.3 (C-1), 49.5 (C-2), 121.1 (C-3), 122.9 (C-20, 20'), 124.4 (C-12, 13), 125.7 (C-18, 18', 22, 22'), 128.2 (C-7, 9), 129.3, (C-8), 129.4 (C-6, 10), 129.7 (C-19, 19', 21, 21'), 129.8 (C-14, 15), 131.2 (C-16), 135.9 (C-11), 146.8 (C-17, 17'), 150.2 (C-5), 155.3 (C-4);

[0068] ESI-HRMS, m / z: Calcd for C 28 H 26 NO 2 S [M + H] + : 440.1679, Found: 440.1676.

[0069] Example 5

[0070] Prepare 14 groups of 10 μM aqueous solutions of the sensing material compound 3c;

[0071] Add 10 equiv. of different aromatic explosives to 13 of these groups for standby;

[0072] Select a fluorescence spectrometer, set appropriate parameters, and test the fluorescence emission spectra of the 14 groups of solutions. The results are as Figure 3 shown.

[0073] From Figure 3It can be found that the aqueous solution of the sensing material compound 3c has strong fluorescence. When PA (2,4,6-trinitrophenol, i.e., picric acid), DNP (2,4-dinitrophenol), DNA (2,4-dinitroaniline), and NA (2-nitroaniline) are added, it will cause a strong quenching of the fluorescence of the solution. However, when TNT (2,4,6-trinitrotoluene), DNT (2,4-dinitrotoluene), NT (4-nitrotoluene), NB (2-nitrobenzene), NBA (4-nitrobenzaldehyde), NBAc (4-nitrobenzoic acid), HBAc (4-hydroxybenzoic acid), Phenol (phenol), and NM (nitromethane) are added, there is no obvious change in the fluorescence of the solution. This indicates that the fluorescent material can effectively identify a variety of aromatic explosives in the liquid state.

[0074] Example 6

[0075] In this example, the response time of the sensing material compound 3c was tested. The specific process was as follows:

[0076] Four groups of 10 μM aqueous solutions of the sensing material compound 3c were prepared;

[0077] One group of the solution was added to a quartz cuvette and placed in a fluorescence spectrometer. 10 equiv. of NACs solution was quickly added, and the relationship between the maximum intensity and time was recorded.

[0078] Without any external force, the fluorescence intensity decreased strongly and rapidly, and the fluorescence weakened to the minimum within 10 s and no longer changed significantly.

[0079] From Figure 4 It can be found that when 20 equivalents of explosives were added to the aqueous solution of the sensing material compound 3c, the fluorescence of compound 3c was quickly quenched within 10 s. This indicates that compound 3c can quickly detect four aromatic explosives.

[0080] Example 7

[0081] In this example, a portable test strip loaded with the sensing material compound 3c was prepared and a visual recognition test was carried out. The specific process was as follows:

[0082] Five blank filter papers of the same size were cut and set aside for use;

[0083] 10 mL of a solution of the fluorescent material compound 3c (DCM, 10 -3 M) was prepared;

[0084] They were soaked in a solution of the fluorescent material 3c (DCM, 10 -3 M) for 1 minute, taken out and dried, and the preparation of the portable test strip was completed;

[0085] On the filter paper strips of the 4 groups of fluorescent material compounds 3c, 3 drops of aromatic explosives (10 -7 M) were respectively added dropwise. Under the ultraviolet lamp at 365 nm, the results as shown Figure 5 could be observed.

[0086] Example 8

[0087] In this example, the sensing material compound 3c was used to detect NACs in actual water samples. The specific process was as follows:

[0088] Tap water was used as the actual water sample and THF was used to jointly prepare a solution of compound 3c (10 μM, H 2 O / THF, 9 / 1, v / v);

[0089] Subsequently, NACs solutions with known concentrations were respectively added, and their fluorescence intensities were measured;

[0090] By comparing with the calculated concentration of NACs obtained from the titration fitting straight line, the experiment was repeated three times, and the recovery rate and relative standard deviation (RSD) were calculated to characterize the detection effect of the fluorescent material compound 3c. The results of relevant tests and calculations are summarized in Table 1.

[0091] Table 1

[0092]

[0093]

[0094] It can be seen from the table that the recovery rate range of the fluorescent material compound 3c for the simulated experiment detection of NACs is 99.43% - 100.80%, and the relative standard deviation is less than 1%. Compared with the actual water sample detection of the reported probes, it has a better effect. This indicates that the fluorescent material compound 3c as a NACs probe can more accurately detect PA, DNA, DNP, and NA in actual water samples and has the potential for application in actual detection.

[0095] The above embodiments are the preferred embodiments of the present invention, but the embodiments of the present invention are not limited by the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications made without departing from the spirit and principle of the present invention shall be equivalent replacement methods and are all included in the protection scope of the present invention.

Claims

1. Compounds of formula I: in, R1 and R2 are independently selected from C1-C4 alkyl, phenyl, or R1 and R2 and the atoms connected thereto form a 9-21-membered heteroaryl; the heteroaryl is unsubstituted or substituted by one or more C1-C4 alkyl; R3 is selected from C1-C4 alkyl and phenyl; the phenyl is unsubstituted or substituted by one or more C1-C4 alkyl.

2. The compound of formula (I) according to claim 1, characterized in that: The R1 and R2 and the atoms connected thereto form a group selected from carbazolyl, indolyl, dihydroindole and dihydroacridinyl.

3. The compound of formula (I) according to claim 1, characterized in that: The compound of formula I is selected from 4. A method for preparing a compound of formula I-1, comprising the following steps: The compound of formula II With the compound of formula III Reaction is carried out to obtain a compound of formula I-1 Wherein, X is a halogen; Y is selected from O, N, S; R a , R b are independently selected from hydrogen, C1-C4 alkyl, phenyl, or R1 and R2 and the atoms connected thereto form a 9-21-membered heteroaryl; the heteroaryl is unsubstituted or substituted by one or more C1-C4 alkyl groups; And R a , R b are not hydrogen at the same time; R3 is defined as in any one of claims 1 to 3.

5. The preparation method according to claim 4, characterized in that: The compound of formula I-1 is selected from:

6. The preparation method according to claim 4, characterized in that: The reaction satisfies at least one of the following conditions: (a) the reaction is a Suzuki-Miyaura coupling reaction; (b) The catalyst used in the reaction includes any one of Pd(PPh3)2Cl2, Pd(PPh3)4, PdCl2(dppf), PdCl2, Pd(OAc)2, NiCl2(dppf), and Ni(COD)2; (c) the reaction is carried out under alkaline conditions; (d) the reaction temperature is 30 to 90° C.; (e) The reaction time is 6 to 12 hours.

7. A fluorescent sensing material, characterized in that: The invention comprises the compound of formula I-1 as claimed in claim 4.

8. A fluorescence detection device, characterized in that: The method comprises the compound of formula I-1 as described in claim 4 or the fluorescent sensing material as described in claim 7.

9. The fluorescence detection device according to claim 8, characterized in that: The fluorescence detection device comprises a fluorescence detection test paper.

10. Use of the compound of formula I-1 as claimed in claim 4, or the fluorescent sensing material as claimed in claim 7, or the fluorescent detection device as claimed in claim 8 or 9 in the detection of aromatic explosives.

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