A poly(alpha-ketoselenoamide) compound and a preparation method and application thereof

Abstract

The application discloses a kind of poly (alpha-ketone selenium amide) compound and its preparation method and application.The application is by under protective atmosphere, taking elemental selenium, poly alpha-halo aryl ethanone compound monomer and polyamine compound monomer mixing, adding base and organic solvent, stirring is carried out polymerization reaction;After reaction, precipitation, drying preparation the poly (alpha-ketone selenium amide) compound of described.The application directly converts abundant and economic, stable, low-toxicity elemental selenium into novel selenium-containing functional polymer, enriches the structure of selenium-containing polymer;Reaction atomic utilization rate is 100%, no toxic and harmful byproduct is generated;Reaction is carried out at room temperature, without metal catalyst, simple operation, polymerization reaction yield is high;The obtained series poly (alpha-ketone selenium amide) has non-traditional luminescent property, and is expected to be applied in optoelectronic device field.

Description

Technical Field

[0001] This invention belongs to the fields of organic chemistry, polymer chemistry and materials science, and specifically relates to a poly(α-ketoselenoamide) compound and its preparation method and application. Background Technology

[0002] Selenium-containing polymers are a class of functional polymers with unique structures, properties, and applications. Due to their unique metal ion coordination, high refractive index, high carrier mobility, dynamic covalent bonds, stimulus responsiveness, and biomedical activity, they are widely used in many fields such as heavy metal detection, optoelectronic devices, biodegradable micelles, and drug delivery systems. However, the types of selenium-containing polymers reported so far are still very limited, mainly including monoselenopolymers, diselenopolymers, and selenium-containing heterocyclic polymers. They are usually prepared from selenium-containing monomers such as diselenoides, selenophenols, and sodium selenide through ring-opening polymerization, free radical polymerization, and transition metal-catalyzed polycondensation (Small, 2018, 14, 1703732). Therefore, the key limitations in the development of selenium-containing polymers are the lack of economical and safe monomers, the lack of effective and convenient synthetic methods, and the poor stability of selenium involved in covalent bonds.

[0003] Elemental selenium is a common byproduct in many metal refining industries, most commonly in the electrolytic refining of copper and as a decolorizing agent in glass manufacturing. Selenium's unique properties can be attributed to its larger atomic radius than its group of oxygen and sulfur atoms, coupled with its relatively low electronegativity. This combination results in its low bond energy ((C-Se) ~244 kJ / mol < (CS) ~272 kJ / mol). Therefore, elemental selenium, as an economical, low-toxicity, and stable industrial raw material, is an ideal selenium source for synthesizing selenium-containing functional polymers. Furthermore, multicomponent polymerization, as an efficient and convenient method for polymer construction, offers advantages such as simple raw materials, mild conditions, convenient operation, diverse products, and atom economy, allowing for the one-step conversion of simple monomers into polymers with rich structures and functions. Developing multicomponent polymerization based on elemental selenium holds promise for the efficient, rapid, and safe preparation of selenium-containing functional polymers from elemental selenium. Summary of the Invention

[0004] In order to address the shortcomings of existing technologies and to develop novel selenium-containing polymer structures, the primary objective of this invention is to provide a poly(α-ketoselenoamide) compound.

[0005] Another objective of this invention is to provide a method for preparing the above-mentioned poly(α-ketoselenoamide) compounds with different structures. In an organic solvent, under alkaline conditions, elemental selenium, α-haloaryl ketone monomers, and amine monomers are reacted, and post-treatment yields poly(α-ketoselenoamide). This invention directly converts abundant, economical, stable, and low-toxic elemental selenium into novel selenium-containing functional polymers, enriching the structure of selenium-containing polymers; the reaction has 100% atom utilization and produces no toxic or harmful byproducts; the reaction is carried out at room temperature, requires no metal catalyst, is simple to operate, and has a high polymerization yield; the resulting series of poly(α-ketoselenoamides) possesses non-traditional luminescent properties and is expected to be applied in the field of optoelectronic devices.

[0006] Another object of the present invention is to provide the application of the above-mentioned poly(α-ketoselenoamide) compounds.

[0007] The objective of this invention is achieved through the following technical solution:

[0008] A poly(α-ketoselenoamide) compound is obtained by polymerization of elemental selenium, a multi-component α-haloaryl ethyl ketone monomer, and a multi-component amine monomer.

[0009] Preferably, the monomer of the multi-component α-haloaryl ethyl ketone compound is a binary, trivalent, or tetravalent α-haloaryl ethyl ketone compound monomer; and the multi-component amine compound is a binary, trivalent, or tetravalent amine compound.

[0010] More preferably, the structural formula of the binary α-haloaryl ethyl ketone monomer is:

[0011]

[0012] Where X is Cl, Br, or I, and R 5 It represents a subarylene.

[0013] More preferably, the binary α-haloaryl ethyl ketone compound is selected from any one of the following:

[0014]

[0015] Where X is Cl, Br, or I;

[0016] More preferably, the diamine compound is selected from any one of the following:

[0017]

[0018] Where j and k are integers from 1 to 20;

[0019] More preferably, the triamine compound is selected from any one of the following:

[0020]

[0021] Where h is an integer from 1 to 20.

[0022] Preferably, the poly(α-ketoselenoamide) compound has the following linear structure of Formula 1 and hyperbranched / crosslinked structure of Formula 2:

[0023]

[0024] Where m, n, and i are integers between 2 and 400; R 1 For a aryl group, R 2 R is an alkylene or alkeneoxy group. 3 H or alkyl, R 4 It is a pentaalkyl group.

[0025] A method for one-pot preparation of the above-mentioned poly(α-ketoselenoamide) compounds includes the following steps:

[0026] Under a protective atmosphere, elemental selenium, a multi-component α-haloaryl ethyl ketone monomer, and a multi-component amine monomer were mixed, and an alkali and an organic solvent were added. The mixture was stirred to carry out a polymerization reaction. After the reaction was completed, the mixture was precipitated and dried to obtain the poly(α-ketoselenoamide) compound.

[0027] Preferably, the molar ratio of elemental selenium: carbonyl group of the monomer of the poly(α-haloaryl ketone) compound: amino group of the monomer of the poly(amine) compound is 1-2:1-1.2:1-1.2;

[0028] Preferably, the concentration of the poly(α-haloaryl ethyl ketone) compound in the organic solvent is 0.125–0.5 mol / L, and the organic solvent is hexamethylphosphoric triamine.

[0029] Preferably, the base is one of 1,8-diazabicyclo-bicyclo(5,4,0)-7-undecene or sodium hydride, and the concentration of the base in the organic solvent is 0.125 to 0.75 mol / L.

[0030] Preferably, the stirring speed is 300-600 rpm, the polymerization reaction time is 6-24 h, the polymerization reaction temperature is room temperature, and the precipitation is achieved by adding the mother liquor after the reaction to a precipitant for precipitation.

[0031] More preferably, the precipitant is a mixed solution of n-hexane / dichloromethane; and the room temperature is 20–30°C.

[0032] The aforementioned poly(α-ketoselenoamide) compounds are used as optoelectronic materials and Cu 2+Applications in ion detection.

[0033] Compared with existing technologies, the present invention has the following advantages:

[0034] (1) The preparation method of the present invention converts abundant elemental selenium into high-value selenium-containing functional polymers, thus enriching the structural library of selenium-containing polymers.

[0035] (2) The preparation method of the present invention does not require a metal catalyst, the reaction can be carried out at room temperature, the polymerization conditions are mild, the process is simple, and the polymerization efficiency is high.

[0036] (3) The preparation method of the present invention has good universality and can be applied to a variety of different types of monomers.

[0037] (4) The poly(α-ketoselenoamide) compound prepared by this invention is a non-traditional luminescent material with particularly outstanding properties compared with existing materials.

[0038] (5) The poly(α-ketoselenoamide) compounds prepared in this invention have a positive effect on Cu. 2+ It exhibits fluorescence quenching effect and can be used for qualitative or quantitative detection of Cu. 2+ . Attached Figure Description

[0039] Figure 1 The images show the hydrogen and carbon NMR spectra of the poly(α-ketoselenoamide) compound prepared in Example 1 of this invention in deuterated DMSO.

[0040] Figure 2 The X-ray photoelectron spectra of the poly(α-ketoselenoamide) compound prepared in Example 1 of this invention and the 3d orbitals of elemental selenium (Se) are shown.

[0041] Figure 3 The thermogravimetric curve of the poly(α-ketoselenoamide) compound prepared in Example 1 of this invention is shown.

[0042] Figure 4 The image shows the excitation pattern of the poly(α-ketoselenoamide) P1 solution prepared in Example 1 of this invention under light with a wavelength of 280-400 nm.

[0043] Figure 5 The poly(α-ketoselenoamide) P1 prepared in Example 1 of this invention is used to treat Cu 2+ The fluorescence quenching effect diagram.

[0044] Figure 6 The poly(α-ketothioamide) P4 prepared for Comparative Example 2 of this invention is used to modify Cu. 2+ The fluorescence quenching effect diagram. Detailed Implementation

[0045] The present invention will be further described in detail below with reference to specific embodiments and accompanying drawings, but the implementation of the present invention is not limited thereto.

[0046] A poly(α-ketoselenoamide) compound having the following linear form (Formula 1) and hyperbranched / crosslinked forms (Formula 2):

[0047]

[0048] Where m, n, and i are integers between 2 and 400; R 1 For a aryl group, R 2 R is an alkylene or alkeneoxy group. 3 H or alkyl, R 4 It is a pentaalkyl group.

[0049] A method for one-pot preparation of the above-mentioned poly(α-ketoselenoamide) compounds, wherein the poly(α-ketoselenoamide) compounds include poly(α-ketoselenoamide) compounds with a chain structure of Formula 1 and a hyperbranched / crosslinked structure of Formula 2; the method includes the following steps:

[0050] (1) Under nitrogen conditions, elemental selenium, α-haloaryl ethyl ketone monomers and diamine monomers are mixed, alkali and organic solvent are added, and the mixture is stirred at room temperature to carry out polymerization reaction; after the reaction is complete, the reaction mother liquor is added to a precipitant for precipitation, the precipitate is collected and dried to constant weight, thus obtaining the chain-structured poly(α-ketoselenoamide) compound.

[0051] (2) Under nitrogen conditions, elemental selenium, α-haloaryl ethyl ketone monomers and triamine compounds are mixed, alkali and organic solvent are added, and the polymerization reaction is carried out by stirring at room temperature. After the reaction is complete, the reaction mother liquor is added to a precipitant for precipitation, the precipitate is collected and dried to constant weight, thus obtaining the hyperbranched / crosslinked poly(α-ketoselenoamide) compounds.

[0052] Preferably, the molar ratio of elemental selenium in steps (1) and (2) to the carbonyl group of α-haloaryl ketone compounds to the amino group of amine compounds is 1-2:1-1.2:1-1.2;

[0053] Preferably, the concentration of the α-haloaryl ethyl ketone compound in steps (1) and (2) in the organic solvent is 0.125–0.5 mol / L;

[0054] Preferably, the organic solvent is hexamethylphosphoric acid triamine (HMPA).

[0055] Preferably, the α-haloaryl ethyl ketone compound is a binary α-haloaryl ethyl ketone compound;

[0056] Preferably, the amine compound is a diamine compound or a triamine compound.

[0057] More preferably, the α-haloaryl ethyl ketone compound is selected from any one of the following:

[0058]

[0059] Where X is Cl, Br, or I, and R 5 It represents a subarylene.

[0060] Preferably, the diamine compound is selected from any one of the following:

[0061]

[0062] Where j and k are integers from 1 to 20;

[0063] The triamine compound is selected from any one of the following:

[0064]

[0065] Where h is an integer from 1 to 20.

[0066] Preferably, the base mentioned in steps (1) and (2) is one of 1,8-diazabicyclo-bicyclo(5,4,0)-7-undecene or sodium hydride, and the concentration of the base in the organic solvent is 0.125 to 0.75 mol / L.

[0067] Preferably, the stirring speed in steps (1) and (2) is 300-600 rpm, and the polymerization reaction time is 6-24 h;

[0068] Preferably, the precipitant in steps (1) and (2) is a mixed solution of n-hexane and dichloromethane;

[0069] Preferably, the room temperature in steps (1) and (2) is 20 to 30°C.

[0070] The aforementioned poly(α-ketoselenoamide) compounds are used as optoelectronic materials and Cu 2+ Applications in ion detection.

[0071] Example 1

[0072] A poly(α-ketoselenoamide) compound, the structural formula of which is shown in P1:

[0073]

[0074] The poly(α-ketoselenoamide) compound was prepared by a one-pot direct reaction of elemental selenium, α-haloaryl ethyl ketone, and amine, as shown in equation (I):

[0075]

[0076] The monomers used, 2a, are 1,1'-(1,4-phenylene)bis(2,2-dichloroethane-1-one), and 3a is 1,10-diaminodecane. Monomer 2a was prepared according to the reference (Org. Lett. 2020, 22, 21, 8193-8197). Monomers 1 and 3a are commercially available; in this example, 3a was purchased from Anage Chemicals, and the selenium powder was also purchased from Anage Chemicals.

[0077] The preparation steps of the poly(α-ketoselenoamide) compound are as follows:

[0078] Under a nitrogen atmosphere, monomers 1 (237 mg, 3 mmol), 2a (298 mg, 1 mmol), 3a (172 mg, 1 mmol), and sodium hydride (60% dispersed in mineral oil, 80 mg, 2 mmol) were added sequentially to a 25 mL polymerization tube, followed by 4 mL of hexamethylphosphoric triamine (HMPA). The mixture was stirred at 520 rpm for 15 hours at room temperature. After the reaction was completed, the mother liquor was added dropwise to a mixed solution of n-hexane / dichloromethane, then allowed to stand, filtered, and dried to obtain the poly(α-ketoselenoamide) compound P1.

[0079] Analysis revealed that the yield of poly(α-ketoselenoamide) compound P1 was 93%, with a weight-average molecular weight of 8,900 and a molecular weight distribution of 1.36. The proton NMR spectrum of this poly(α-ketoselenoamide) compound (* represents solvent peaks) is shown below. Figure 1 A in the figure, its carbon NMR spectrum is shown in [reference needed]. Figure 1 B in Figure 1 The chemical shift of 196.41 ppm in B corresponds to the characteristic peak of the carbon atom on C=Se in the poly(α-ketoselenoamide) compound. Figure 1 The chemical shift of B at 190.61 ppm corresponds to the characteristic peak of the carbon atom at C=O in the poly(α-ketoselenoamide) compound. Elemental analysis of the poly(α-ketoselenoamide) compound P1 shows a C:H:N ratio of 41.13:5.62:6.87 (C... 20 H 26 N₂O₂Se₂, calcd. C:H:N = 41.19:5.43:6.86), therefore, the polymer can be identified as a poly(α-ketoselenoamide) compound. Furthermore, Figure 2X-ray photoelectron spectroscopy of the 3d orbitals of the poly(α-ketoselenoamide) compound prepared in Example 1 of this invention and elemental selenium. Figure 2 The presence of selenium in the polymer was observed, and its peak position was completely different from that of elemental selenium, thus ruling out the possibility of residual elemental selenium in the product. Furthermore, Figure 3 The thermogravimetric curve of P1 is shown below. Figure 3 It can be seen that the temperature corresponding to a 5% weight loss is 249℃, indicating that the poly(α-ketoselenoamide) compound P1 has good thermal stability.

[0080] Example 2

[0081] A poly(α-ketoselenoamide) compound, the structural formula of which is shown on P2:

[0082]

[0083] The poly(α-ketoselenoamide) compound was prepared by a one-pot direct reaction of elemental selenium, α-haloaryl ethyl ketone, and amine, as shown in equation (II):

[0084]

[0085] All monomers used were commercially available. 2b was 4,4'-bis(2-bromoacetyl)biphenyl, which was purchased from Anage Chemicals in this example. 3b was 1,3-di-4-piperidinylpropane, which was also purchased from Anage Chemicals in this example. The selenium powder used in this example was also purchased from Anage Chemicals.

[0086] The preparation steps of the poly(α-ketoselenoamide) compound are as follows:

[0087] Under a nitrogen atmosphere, monomers 1 (237 mg, 3 mmol), 2b (396 mg, 1 mmol), 3b (210 mg, 1 mmol), and sodium hydride (60% dispersed in mineral oil, 80 mg, 2 mmol) were added sequentially to a 25 mL polymerization tube, followed by 4 mL of hexamethylphosphoric triamine (HMPA). The mixture was stirred at 520 rpm for 15 hours at room temperature. After the reaction was completed, the mother liquor was added dropwise to a mixed solution of n-hexane / dichloromethane, then allowed to stand, filtered, and dried to obtain the poly(α-ketoselenoamide) compound P2.

[0088] Analysis revealed that the yield of poly(α-ketoselenoamide) compound P2 was 82%, with a weight-average molecular weight of 13,600 and a molecular weight distribution of 1.43.

[0089] Example 3

[0090] A hyperbranched poly(α-ketoselenoamide) compound, the structural formula of which is shown on P3:

[0091]

[0092] The poly(α-ketoselenoamide) compound was prepared by a one-pot reaction of elemental sulfur, α-haloaryl ethyl ketone, and amine, as shown in equation (III):

[0093]

[0094] In this example, monomer 2a is 1,1'-(1,4-phenylene)bis(2,2-dichloroethane-1-one), and 3c is tris(3-aminopropyl)amine. Monomer 2a was prepared according to the reference (Org. Lett. 2020, 22, 21, 8193-8197). Monomers 1 and 3c are commercially available. In this example, 3d was purchased from Anage Chemicals, and the selenium powder was also purchased from Anage Chemicals.

[0095] Under a nitrogen atmosphere, monomers 1 (237 mg, 3 mmol), 2a (298 mg, 1 mmol), 3c (125 mg, 0.66 mmol), and sodium hydride (60% dispersed in mineral oil, 80 mg, 2 mmol) were added sequentially to a 25 mL polymerization tube, followed by 4 mL of hexamethylphosphoric triamine (HMPA). The mixture was stirred at 520 rpm for 15 hours at room temperature. After the reaction was completed, the mother liquor was added dropwise to a mixed solution of hexane / dichloromethane, then allowed to stand, filtered, and dried to obtain the poly(α-ketoselenoamide) compound P3.

[0096] Analysis revealed that the yield of poly(α-ketoselenoamide) compound P3 was 85%, with a weight-average molecular weight of 22,300 and a molecular weight distribution of 1.50.

[0097] Comparative Example 1

[0098] An attempt was made to prepare polyselenoamide compounds using elemental selenium, 1,4-di(bromomethyl)benzene, and amines under the reaction conditions of this invention. The reaction process is as follows:

[0099] Under a nitrogen atmosphere, elemental selenium (237 mg, 3 mmol), 1,4-di(bromomethyl)benzene (262 mg, 1 mmol), 1,10-diaminodecane (172 mg, 1 mmol), and sodium hydride (60% dispersed in mineral oil, 80 mg, 2 mmol) were added sequentially to a 25 mL polymerization tube, followed by 4 mL of hexamethylphosphoric acid triamine (HMPA). The reaction was carried out at room temperature, but the desired polyselenoamide structure could not be obtained. The monomers 1,4-di(bromomethyl)benzene, 1,10-diaminodecane, and selenium powder used were all purchased from Anaiji Chemical.

[0100] Comparative Example 2

[0101] A poly(α-ketothioamide) compound, the structural formula of which is shown on page 4:

[0102]

[0103] The poly(α-ketothioamide) compound was prepared by a one-pot reaction of elemental sulfur, α-haloaryl ethyl ketone, and amine, as shown in equation (IV):

[0104]

[0105] In this example, monomer 2a is 1,1'-(1,4-phenylene)bis(2,2-dichloroethane-1-one), and monomer 3c is 1,10-diaminodecane. Monomer 2a was prepared according to the reference (Org. Lett. 2020, 22, 21, 8193-8197). Monomers 4 and 3c are commercially available; in this example, 3c was purchased from Anaiji Chemical, and sublimed sulfur was purchased from Guangzhou Chemical Reagent Factory.

[0106] The preparation steps of the poly(α-ketothioamide) compound are as follows:

[0107] Monomers 4 (96 mg, 3 mmol), 2a (298 mg, 1 mmol), and 3c (172 mg, 1 mmol) were added sequentially to a 25 mL polymerization tube, followed by 4 mL of N,N-dimethylformamide. The mixture was stirred at 520 rpm for 24 hours at room temperature. After the reaction was completed, the mother liquor was added dropwise to a mixed solution of n-hexane / dichloromethane, then allowed to stand, filtered, and dried to obtain the poly(α-ketothioamide) compound P4.

[0108] Analysis revealed that the yield of poly(α-ketothioamide) compound P4 was 78%, with a weight-average molecular weight of 9,900 and a molecular weight distribution of 1.34.

[0109] Non-traditional luminescent properties of polymers

[0110] Test parameters: excitation wavelength 290nm, test concentration 10 -4 M (solvent is N,N-dimethylformamide), added Cu 2+ The molar ratio of the polymer to the polymer is 5:1.

[0111] All polymers prepared in this invention exhibit luminescent properties. For example, the poly(α-ketoselenoamide) compound P1 prepared in Example 1, its solution ( Figure 4 When excited by light in the 280-400 nm wavelength range, both in its solid and solid states, Cu emits green fluorescence and reacts with Cu.2+ It has a fluorescence quenching effect ( Figure 5 ), is a new type of non-traditional luminescent material.

[0112] Figure 6 The poly-α-ketothioamide P4 prepared for Comparative Example 2 is effective against Cu. 2+ Fluorescence quenching. Among them, the fluorescence intensity of poly(α-ketothioamide) P4 is weaker than that of poly(α-ketoselenoamide) P1, and its fluorescence intensity is also weaker than that of Cu. 2+ The fluorescence quenching effect is poor.

[0113] The above embodiments of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the implementation of the present invention. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively describe all possible implementations here. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention should be included within the scope of protection of the claims of the present invention.

Claims

1. A poly(α-ketoselenoamide) compound, characterized in that, It is obtained by polymerization reaction of elemental selenium, multi-component α-haloaryl ethyl ketone monomers and multi-component amine monomers; wherein the multi-component amine is a binary, ternary or tetramethylamine compound; The structural formula of the monomer of the multi-component α-haloaryl ethyl ketone compound is: Where X is Cl, Br, or I, and R 5 It represents a subarylene.

2. The poly(α-ketoselenoamide) compound according to claim 1, characterized in that, The multi-component α-haloaryl ethyl ketone compounds are selected from any one of the following: Where X is Cl, Br, or I; The diamine compound is selected from any one of the following: Where j and k are integers from 1 to 20; The triamine compound is selected from any one of the following: Where h is an integer from 1 to 20.

3. The poly(α-ketoselenoamide) compound according to claim 1, characterized in that, The poly(α-ketoselenoamide) compounds have the following linear structure (Formula 1) and hyperbranched / crosslinked structure (Formula 2): Formula 1 Formula 2 Where m, n, and i are integers between 2 and 400; R 1 For a aryl group, R 2 R is an alkylene or alkeneoxy group. 3 H or alkyl, R 4 It is a pentaalkyl group.

4. A method for one-pot preparation of the poly(α-ketoselenoamide) compound according to any one of claims 1-3, characterized in that, Includes the following steps: Under a protective atmosphere, elemental selenium, a multi-component α-haloaryl ethyl ketone monomer, and a multi-component amine monomer were mixed, and an alkali and an organic solvent were added. The mixture was stirred to carry out a polymerization reaction. After the reaction was completed, the product was precipitated and dried to obtain the poly(α-ketoselenoamide) compound.

5. The method for one-pot preparation of poly(α-ketoselenoamide) compounds according to claim 4, characterized in that, The molar ratio of elemental selenium to the carbonyl group of the monomer of the poly(α-haloaryl ketone) compound to the amino group of the monomer of the poly(amine) compound is 1-2:1-1.2:1-1.2; The concentration of the poly(α-haloaryl ethyl ketone) compound in the organic solvent is 0.125~0.5 mol / L, and the organic solvent is hexamethylphosphoric triamine.

6. The method for one-pot preparation of poly(α-ketoselenoamide) compounds according to claim 4, characterized in that, The base is one of 1,8-diazabicyclo-bicyclo(5,4,0)-7-undecene or sodium hydride, and the concentration of the base in the organic solvent is 0.125~0.75 mol / L.

7. The method for one-pot preparation of poly(α-ketoselenoamide) compounds according to claim 4, characterized in that, The stirring speed is 300~600 rpm, the polymerization reaction time is 6~24h, the polymerization reaction temperature is room temperature, and the precipitation is carried out by adding the mother liquor after the reaction to a precipitant. The precipitant is a mixed solution of n-hexane and dichloromethane; the room temperature is 20~30℃.

8. The poly(α-ketoselenoamide) compound according to any one of claims 1-3, as a photoelectric material and Cu 2+ Applications in ion detection.

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