Naphthalene ring derivative, synthetic method and application

Abstract

The invention discloses a naphthalene ring derivative, a synthesis method and application, and provides a series of novel naphthalene ring derivatives substituted by different functional groups. Compared with the existing naphthalene ring derivative, the naphthalene ring derivative provided by the invention is a functional group substituted naphthalene ring, and is easily subjected to subsequent chemical conversion and further converted into a high-added-value compound. According to the efficient synthesis method of the naphthalene ring derivative, the substrate applicability is wide, raw materials are cheap, synthesis is easy, high temperature and use of a catalyst are not needed in the reaction process, and various substituent-substituted naphthalene ring compounds can be prepared. The reaction process is milder, the safety is high, the post-treatment difficulty is reduced, high temperature and high pressure are not needed, only visible light irradiation is needed, meanwhile, the use of expensive metal catalysts and organic photocatalysts is avoided, and the post-treatment difficulty is reduced. The method also has the advantages of simple operation, simple steps, high yield, large-scale synthesis and the like.

Description

(I) Technical Field

[0001] This invention belongs to the field of chemical synthesis technology, specifically relating to a multifunctional substituted naphthalene ring derivative, an efficient synthesis method, and its application. (II) Background Technology

[0002] Naphthalene rings, especially polysubstituted naphthalene rings, are among the most representative aromatic structures and are widely found in many natural products, bioactive molecules, and drugs. Furthermore, due to their excellent electronic properties, they are widely used in catalysis (as ligands for metal or organic catalysts), optoelectronic materials, and fluorescent bioimaging probes. For example, the fluorescent material fluoranthene contains a naphthalene ring skeleton; the commercially available antidepressant duloxetine and the antihypertensive drug propranolol also belong to polysubstituted naphthalene ring structures. With the widespread application of polysubstituted naphthalene ring skeletons in various fields, the development of simple and efficient naphthalene ring skeleton molecules is increasingly attracting the attention of chemists. The highly selective synthesis of specific naphthalene ring skeletons that are easily modified later is currently an important research trend.

[0003] Naphthalene ring derivatives can be directly constructed via an intramolecular didehydrogenation-Diesell-Alder reaction of styrene. However, this intramolecular reaction requires harsh reaction conditions and often leads to the polymerization of styrene. Compared to intramolecular reactions, intermolecular dehydrogenation-Diesell-Alder reactions provide a more direct and efficient route for the synthesis of polysubstituted naphthalenes. However, the high reaction energy barrier usually requires harsh reaction conditions such as high temperatures, which poses a significant challenge to achieving chemoselectivity and regioselectivity. In the past decade, photoredox-catalyzed single-electron oxidation of olefins has become a promising strategy to overcome this limitation. The Lei Aiwen research group developed an elegant [4+2] cyclization / dehydration reaction between styrene and alkynes. This reaction uses a photo / cobalt dual-catalyst system to construct the naphthalene ring. Styrene is photo-excited to generate a radical cation intermediate via single-electron oxidation of an acridinium salt, which is then converted to a naphthalene ring via C2O2. / C The relay catalytic cycle completes the conversion and releases hydrogen. In such systems, the formation of radical cationic intermediates via single-electron transfer (SET) of the diene component is crucial. Although some progress has been made in the photocatalytic synthesis of naphthalene rings, limitations remain, such as the difficulty in synthesizing starting materials and the limited substrate range.

[0004] Naphthalene ring derivatives are an important class of organic fluorescent materials with significant application value in the field of bioimaging. These materials are based on a single-photon excitation mechanism, typically using high-energy, short-wavelength excitation light to emit low-energy, long-wavelength fluorescence.

[0005] Currently, there is no universal [4+2] cycloaddition system that can simultaneously accommodate electron-deficient dienes and electron-rich and electron-deficient dienophiles to achieve the synthesis of naphthyl ring derivatives. (III) Summary of the Invention

[0006] The purpose of this invention is to provide a novel, efficient method and application for the photocatalytic synthesis of naphthalene ring derivatives. This method utilizes a [4+2]-dominant intermolecular cycloaddition reaction between olefin and alkyne derivatives, avoiding the use of high temperature, high pressure, and expensive metal and organic photocatalysts. It exhibits good functional group tolerance, excellent regioselectivity and stereoselectivity, and follows a novel triplet reaction pathway, enabling the synthesis of naphthalene rings with different functional group substitutions, significantly expanding the substrate types and scope. This invention solves the problems of harsh reaction conditions, expensive reagents, narrow substrate range, and low selectivity in existing technologies.

[0007] The technical solution adopted in this invention is:

[0008] In a first aspect, the present invention provides a naphthalene ring derivative, the structural formula of which is shown in Figure 1:

[0009] 1

[0010] In compound 1, R 1 It is any one of hydrogen, C1-C5 alkyl, silane or aryl; R 2 It is any one of C1-C5 alkyl, substituted phenyl, or aryl; R 5 It is any one of hydrogen, C1-C2 alkyl or aryl; R 6 It is any one of hydrogen, C1-C5 alkyl, C1-C5 alkoxy, aryl, and halogen.

[0011] Furthermore, R is preferred. 1 The components are hydrogen, ethyl, methyl formate, benzene, thiophene, formaldehyde, trimethylsilyl, and R. 2 It is phenyl, 4-propylphenyl, or thiophene; R 5 It is hydrogen; R 6 It is hydrogen, 7-bromo, or 7-methoxy.

[0012] Furthermore, the naphthalene ring derivative is one of the following:

[0013]

[0014] 1-1 1-2

[0015]

[0016] 1-3 1-4.

[0017] Secondly, the present invention provides an efficient method for synthesizing a naphthalene ring derivative (1), wherein the method uses compound A and compound B as raw materials to synthesize the naphthalene ring derivative (1) under organic solvent and light irradiation.

[0018]

[0019] AB 1

[0020] In compound A, R 1 It is any one of hydrogen, C1-C5 alkyl, silane or aryl; R 2 It is any one of hydrogen, C1-C5 alkyl, substituted phenyl or aryl;

[0021] R in compound B 3 It is any one of phenyl or substituted phenyl, wherein the substituent of the substituted phenyl is R. 6 ;R 4 It is any one of alkylsulfonyl, alkylsulfinyl, halogen, arylsulfonyl, or arylsulfinyl; R 5 It is any one of hydrogen, C1-C2 alkyl, or aryl; R 6 It is hydrogen, a polysubstituted C1-C5 alkoxy group, or a polysubstituted halogen;

[0022] In compound 1, R 1 R 2 Same as compound A; R 5 R 6 Same as compound B.

[0023] Preferred, R 1 The components are hydrogen, ethyl, methyl formate, phenyl, 4-propylphenyl, thiophene, formaldehyde, and R. 2 It is hydrogen, phenyl, or trimethylsilane; R 3 It is phenyl, 7-methoxyphenyl, 7-bromophenyl; R 4 It is methanesulfonyl (Ms), chlorine, methylsulfinyl, benzenesulfonyl; R 5 It is hydrogen; R 6 It can be hydrogen, 7-methoxy, or 7-bromine.

[0024] Preferably, the organic solvent is any one of acetonitrile, methanol, ethanol, dioxane, dichloromethane, dichloroethane, toluene, chlorobenzene, N,N-dimethylformamide, or dimethyl sulfoxide, with acetonitrile being the most preferred.

[0025] Preferably, the light source is any wavelength in the range of 365~470 nm, and more preferably 400 nm.

[0026] Preferably, the method is carried out according to the following steps: organic solvent, compound A and compound B are added sequentially to the reaction tube, the reaction tube is sealed, argon gas is evacuated three times, and then the reaction is carried out at room temperature for 1 to 15 h under light source irradiation. After removing the solvent, the product is separated and purified by silica gel column chromatography and concentrated to dryness under reduced pressure to obtain the naphthalene ring derivative (1).

[0027] Preferably, the ratio of compound B to compound A is 1:1 to 1:4 (preferably 1:2), and the volume of organic solvent used is 5 to 30 mL / mmol (preferably 20 mL / mmol) based on the amount of compound B.

[0028] Preferably, the silica gel column separation and purification method is as follows: the product is separated by reverse silica gel chromatography column, the eluent is a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:5-10, TLC detection is performed, the developing solvent is a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:5-10, the eluent with an Rf value of 0.6 is collected, and the solution is concentrated to dryness under reduced pressure to obtain the naphthalene ring derivative (1).

[0029]

[0030] Thirdly, the present invention provides an application of the naphthalene ring derivative in the preparation of luminescent materials.

[0031] Furthermore, the luminescent material includes biopharmaceutical intermediates, cosmetic raw materials, biological probes, and fluorescent dyes.

[0032] Compared with the prior art, the beneficial effects of the present invention are mainly reflected in:

[0033] (1) This invention provides a series of new naphthalene ring derivatives with different functional groups substituted. Compared with existing naphthalene ring derivatives, the naphthalene rings of this invention with functional groups substituted are more likely to undergo subsequent chemical transformations and be further transformed into high value-added compounds.

[0034] (2) This invention provides an efficient method for synthesizing naphthalene ring derivatives. The method has broad substrate applicability, uses inexpensive and easily synthesized raw materials, and does not require high temperature or catalyst during the reaction process. It can prepare naphthalene ring compounds with various substituents. The reaction process is milder, safer, and reduces the difficulty of post-processing. It does not require high temperature or high pressure, but only visible light irradiation, thus avoiding the use of expensive metal catalysts and organic photocatalysts and reducing the difficulty of post-processing. This invention also has the advantages of simple operation, concise steps, high yield, and large-scale synthesis.

[0035] (3) The naphthalene ring derivatives provided by this invention can absorb light of 365~410nm at low concentrations and emit fluorescence with a longer wavelength (Example 8), demonstrating their application potential in biological probes and fluorescent dyes. This provides more options for the source of raw materials for further research on the application of multi-substituted naphthalene rings in biomedicine, cosmetics, and luminescent materials. (iv) Description of the attached drawings

[0036] Figure 1 For product 1-1 of Example 1 1 HNMR spectrum (600 MHz, DMSO-d6).

[0037] Figure 2 For product 1-1 of Example 1 13 CNMR spectrum (150 MHz, DMSO-d6).

[0038] Figure 3 Products 1-2 of Example 5 1 HNMR spectrum (600 MHz, DMSO-d6).

[0039] Figure 4 Products 1-2 of Example 5 13 CNMR spectrum (150 MHz, DMSO-d6).

[0040] Figure 5 Products 1-3 of Example 6 1 HNMR spectrum (600 MHz, DMSO-d6).

[0041] Figure 6 Products 1-3 of Example 6 13 CNMR spectrum (150 MHz, DMSO-d6).

[0042] Figure 7 Products 1-4 of Example 7 1 HNMR spectrum (600 MHz, DMSO-d6).

[0043] Figure 8 Products 1-4 of Example 7 13 CNMR spectrum (150 MHz, DMSO-d6).

[0044] Figure 9 Example 8: Ultraviolet emission spectrum of compound 1-1. (V) Detailed Implementation Methods

[0045] The present invention will be further described below with reference to specific embodiments, but the scope of protection of the present invention is not limited thereto: the room temperature of the present invention refers to 25-30℃.

[0046] Example 1: Synthesis of naphthalene ring derivative (1-1)

[0047]

[0048] B1 A1 1-1

[0049] 50.2 mg of 3-methanesulfonyl-4-phenylmaleimide (B1, 0.2 mmol) and 40.2 mg of phenylacetylene (A1, 0.4 mmol) were placed in a 25 mL reaction tube, followed by the addition of 4 mL of acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 4 h under 400 nm light. After the reaction was complete, the solvent was removed, and the product was separated by reversed-phase silica gel chromatography. The eluent was a mixture of ethyl acetate and petroleum ether (v / v, 1:10). TLC was performed using a mixture of ethyl acetate and petroleum ether (v / v, 1:10) as the developing solvent. The eluent with an Rf value of 0.6 was collected and concentrated to dryness under reduced pressure to give 45.9 mg of a white solid, namely 5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione (1-1), with a yield of 84%. 1 HNMR image see Figure 1 , 13 See the C NMR spectrum. Figure 2 .

[0050] 1 H NMR (600 MHz, DMSO- d 6 ) δ 11.34 (s, 1H), 8.94 – 8.88 (m, 1H), 7.92(d, J = 8.4 Hz, 1H), 7.83 (ddd, J = 8.4, 6.6, 1.2 Hz, 1H), 7.72 (ddd, J =8.4, 6.6, 1.2 Hz, 1H), 7.65 – 7.58 (m, 2H), 7.57 – 7.52 (m, 3H).

[0051] 13 C NMR (151 MHz, DMSO- d 6) δ 171.0, 169.9, 147.3, 139.2, 134.4, 131.9,130.2, 129.9, 129.4, 129.2, 128.9, 128.9, 127.2, 127.0, 124.9, 119.3. HRMS(ESI, m / z ): Calcd for C 18 H 12 NO2 + [M+H] + : 274.0863, found: 274.0862.

[0052] Example 2: Synthesis of naphthalene ring derivative (1-1)

[0053]

[0054] B2 A1 1-1

[0055] 41.5 mg of 3-chloro-4-phenylmaleimide (B2, 0.2 mmol) and 40.2 mg of phenylacetylene (A1, 0.4 mmol) were placed in a 25 mL reaction tube, followed by the addition of 4 mL of acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 4 h under 400 nm light. After the reaction was complete, the solvent was removed using the method described in Example 1, and the product was separated by column chromatography to obtain 29.5 mg of a white solid. The structure of this solid was identified using the method described in Example 1, yielding 5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione (1-1) in 55% yield.

[0056] Example 3: Synthesis of naphthalene ring derivative (1-1)

[0057]

[0058] B3 A1 1-1

[0059] 41.0 mg of 3-methylsulfinyl-4-phenylmaleimide (B3, 0.2 mmol) and 40.2 mg of phenylacetylene (A1, 0.4 mmol) were placed in a 25 mL reaction tube, followed by the addition of 4 mL of acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 4 h under 400 nm light. After the reaction was complete, the solvent was removed using the method described in Example 1, and the product was separated by column chromatography to obtain 12.0 mg of a white solid. The structure of this solid was identified using the method described in Example 1, yielding 5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione (1-1) in 22% yield.

[0060] Example 4: Synthesis of naphthalene ring derivative (1-1)

[0061]

[0062] B4 A1 1-1

[0063] 62.6 mg of 3-benzenesulfonyl-4-phenylmaleimide (B4, 0.2 mmol) and 40.2 mg of phenylacetylene (A1, 0.4 mmol) were placed in a 25 mL reaction tube, followed by the addition of 4 mL of acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 4 h under 400 nm light. After the reaction was complete, the solvent was removed using the method described in Example 1, and the product was separated by column chromatography to obtain 35.6 mg of a white solid. The structure of this solid was identified using the method described in Example 1, yielding 5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione (1-1) in 22% yield.

[0064] Example 5: Synthesis of Naphthalene ring derivatives (1-2)

[0065]

[0066] B5 A1 1-2

[0067] 56.2 mg of 3-methanesulfonyl-4-methoxyphenylmaleimide (B5, 0.2 mmol) and 40.2 mg of phenylacetylene (A1, 0.4 mmol) were placed in a 25 mL reaction tube, followed by the addition of 4 mL of acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 24 h under 400 nm light. After the reaction was complete, the solvent was removed using the method described in Example 1, and the product was separated by column chromatography to obtain 24.8 mg of a yellow solid, namely 7-methoxy-5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione, in 41% yield. 1 See H NMR spectrum Figure 3 , 13 See the C NMR spectrum. Figure 4 .

[0068] 1 H NMR (600 MHz, DMSO- d 6 ) δ 11.23 (s, 1H), 8.79 (d, J = 9.0 Hz, 1H), 7.59 (dd, J= 9.0, 5.4 Hz, 3H), 7.56 – 7.51 (m, 3H), 7.48 (dd, J = 9.4, 2.4Hz, 1H), 7.22 (d, J = 2.4 Hz, 1H), 3.74 (s, 3H). 13 C NMR (151 MHz, DMSO- d 6 ) δ171.0, 170.0, 159.7, 145.4, 139.4, 136.3, 129.9, 129.3, 129.3, 128.8, 127.3,126.6, 123.7, 122.1, 119.9, 105.9, 55.6. HRMS (ESI, m / z ): Calcd for C 19 H 14 NO3 + [M+H] + :304.0968, found: 304.0969.

[0069] Example 6: Synthesis of Naphthalene ring derivatives (1-3)

[0070]

[0071] B6 A2 1-3

[0072] 56.2 mg of 3-methanesulfonyl-4-methoxyphenylmaleimide (B6, 0.2 mmol) and 40.2 mg of phenylacetylene (A2, 0.4 mmol) were placed in a 25 mL reaction tube, followed by the addition of 4 mL of acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 4 h under 400 nm light. After the reaction was complete, the solvent was removed using the method described in Example 1, and the product was separated by column chromatography to obtain 65.4 mg of a white solid, namely 7-bromo-5-(4-propylphenyl)-1H-benzo[e]isoindole-1,3(2H)-dione, in 83% yield. 1 See H NMR spectrum Figure 5 , 13 See the C NMR spectrum. Figure 6 .

[0073] 1 H NMR (400 MHz, CDCl3) δ 8.91 (d, J = 9.0 Hz, 1H), 8.22 (d,J = 1.98Hz, 1H), 7.85 (s, 1H), 7.84 (m, 2H), 7.75 (s, 1H), 7.40 (m, 4H), 2.74 (m,2H), 1.79 (dt, J = 15.0, 7.2 Hz, 2H), 1.06 (t, J = 7.2 Hz, 3H). 13 C NMR (101MHz, CDCl3) δ 168.9, 168.1, 147.6, 143.6, 136.1, 135.8, 132.8, 131.5, 129.6,129.6, 129.0, 127.3, 126.7, 126.6, 124.0, 120.7, 76.7, 37.9, 24.5, 14.0. HRMS(ESI, m / z ): Calcd for C 21 H 17 BrNO2 + [M+H] + : 394.0437, found: 394.0439.

[0074] Example 7: Synthesis of Naphthalene ring derivatives (1-4)

[0075]

[0076] B7 A2 1-4

[0077] 3-Methanesulfonyl-4-methoxyphenylmaleimide (56.2 mg) and phenylethynyltrimethylsilane (69.6 mg) were placed in a 25 mL reaction tube, followed by the addition of 4 mL acetonitrile as the reaction solvent. The reaction tube was sealed, and the mixture was purged three times with argon gas. The reaction was carried out at room temperature for 4 h under 400 nm light. After the reaction was complete, the solvent was removed using the method described in Example 1, and the product was separated by column chromatography to obtain 35.1 mg of a white solid, namely 5-(thiophene-2-yl)-4-(trimethylsilyl)-1H-benzo[e]isoindole-1,3(2H)-dione, in 50% yield. 1 See H NMR spectrum Figure 7 , 13 See the C NMR spectrum. Figure 8 .

[0078] 1 H NMR (600 MHz, DMSO- d 6) δ 11.31 (s, 1H), 8.96 (d, J = 8.4 Hz, 1H),7.80 – 7.74 (m, 1H), 7.60 (ddd, J = 8.4, 6.6, 1.2 Hz, 1H), 7.55 – 7.50 (m,3H), 7.39 (d, J = 8.4 Hz, 1H), 7.36 – 7.28 (m, 2H), -0.05 (s, 9H). 13 C NMR (151 MHz, DMSO-) d 6 ) δ 171.2, 171.0, 153.9, 141.0, 136.4, 135.0, 132.9, 130.9,129.8, 129.2, 128.7, 128.6, 128.0, 127.7, 124.5, 1.6. HRMS (ESI, m / z ): Calcdfor C 21 H 20 NO2Si + [M+H] + :346.1258, found: 346.1257.

[0079] Example 8: Fluorescence emission spectrum of naphthalene ring derivative 1-1

[0080] The 5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione (1-1) prepared in Example 1 was used to prepare a 0.01 mM solution with acetonitrile as the solvent. The solution was detected by fluorescence spectroscopy at room temperature. Under illumination at 400 nm, photoluminescence was induced, and fluorescence was excited at room temperature with a significant red shift in the emission wavelength. The excited fluorescence wavelength ranged from 408 to 525 nm. The fluorescence emission spectrum is shown below. Figure 9 It can be seen that the acetonitrile solution of 5-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione (1-1) emits obvious fluorescence.

[0081] Compounds 1-2, 1-3, and 1-4 were tested using the same method, and the results showed that they all exhibited photoluminescence and could be used to prepare luminescent materials.

[0082] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Any simple modifications, equivalent substitutions, and improvements made by those skilled in the art to the above embodiments without departing from the scope of the technical solution of the present invention, based on the technical essence of the present invention, shall still fall within the protection scope of the technical solution of the present invention.

Claims

1. A naphthalene ring derivative, with the structural formula shown in Figure 1: 1 In compound 1, R 1 It is any one of hydrogen, C1-C5 alkyl, silane or aryl; R 2 It is any one of C1-C5 alkyl, substituted phenyl, or aryl; R 5 It is any one of hydrogen, C1-C2 alkyl or aryl; R 6 It is any one of hydrogen, C1-C5 alkyl, C1-C5 alkoxy, aryl, and halogen.

2. The naphthalene ring derivative as described in claim 1, characterized in that, R 1 The components are hydrogen, ethyl, methyl formate, benzene, thiophene, formaldehyde, trimethylsilyl, and R. 2 It is phenyl, 4-propylphenyl, or thiophene; R 5 It is hydrogen; R 6 It is hydrogen, 7-bromo, or 7-methoxy.

3. The naphthalene ring derivative as described in claim 1, characterized in that, The naphthalene ring derivative is one of the following: 1-1 1-2 1-3 1-4。 4. A highly efficient method for synthesizing the naphthalene ring derivative of claim 1, characterized in that, The method uses compound A and compound B as raw materials to synthesize naphthalene ring derivative 1 under organic solvent and light irradiation; AB 1 In compound A, R 1 It is any one of hydrogen, C1-C5 alkyl, silane or aryl; R 2 It is any one of hydrogen, C1-C5 alkyl, substituted phenyl or aryl; R in compound B 3 It is any one of phenyl or substituted phenyl, wherein the substituent of the substituted phenyl is R. 6 ;R 4 It is any one of alkylsulfonyl, alkylsulfinyl, halogen, arylsulfonyl, or arylsulfinyl; R 5 It is any one of hydrogen, C1-C2 alkyl, or aryl; R 6 It is hydrogen, a polysubstituted C1-C5 alkoxy group, or a polysubstituted halogen; In compound 1, R 1 R 2 Same as compound A; R 5 R 6 Same as compound B.

5. The method as described in claim 4, characterized in that, The organic solvent is any one of acetonitrile, methanol, ethanol, dioxane, dichloromethane, dichloroethane, toluene, chlorobenzene, N,N-dimethylformamide, or dimethyl sulfoxide.

6. The method as described in claim 4, characterized in that, The method is carried out as follows: organic solvent, compound A and compound B are added sequentially to the reaction tube, the reaction tube is sealed, argon gas is evacuated three times, and then the reaction is carried out at room temperature for 1 to 15 hours under light source irradiation. After removing the solvent, the product is separated and purified by silica gel column chromatography and concentrated to dryness under reduced pressure to obtain the naphthalene ring derivative.

7. The method as described in claim 4, characterized in that, The ratio of compound B to compound A in terms of their amounts is 1:1 to 1:4, and the volume of organic solvent used is 5 to 30 mL / mmol based on the amount of compound B.

8. The method as described in claim 4, characterized in that, The method for separation and purification using silica gel column chromatography is as follows: the product is separated by reverse silica gel chromatography column, the eluent is a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:5-10, TLC detection is performed, the developing solvent is a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:5-10, the eluent with an Rf value of 0.6 is collected, and the solution is concentrated to dryness under reduced pressure to obtain the naphthalene ring derivative.

9. The use of the naphthalene ring derivative of claim 1 in the preparation of luminescent materials.

10. The application as described in claim 9, characterized in that, The luminescent materials include biopharmaceutical intermediates, cosmetic raw materials, biological probes, and fluorescent dyes.

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