CN101486901A - Luminescent material with platinum center having sensing function to halogenated hydrocarbon, method and use - Google Patents
Luminescent material with platinum center having sensing function to halogenated hydrocarbon, method and use Download PDFInfo
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Abstract
The invention relates to a sensing material for detecting the halogenated hydrocarbon, which is characterized in that the center is the divalent platinum; the two ligands coordinated with the platinum are 2-phenylpyridine; and simultaneously, the phenyl is provided with the aryl substituent. The sensing material comprises platinum, 2-phenylpyridine ligands and aryl on the phenyl or oligomer and polymer further constructed by aryl. The aryl comprises the further constructed oligomer or polymer as well as ramification of aryl. The detection method is realized through detecting the change of the fluorescence intensity of the luminescent material by using fluorescence means. The provided luminescent material is applicable to the detection of the volatile halogenated hydrocarbon.
Description
Technical field
The present invention relates to a kind ofly has luminescent material, the method at the platinum center of sensing function to halohydrocarbon, with and in the application of halohydrocarbon context of detection.
Background technology
Methylene dichloride, trichloromethane, tetracol phenixin, 1,2-ethylene dichloride, 1,1,1-trichloroethane, vinyl trichloride, 1,1,2, halohydrocarbon such as 2-tetrachloroethane, methenyl bromide, trieline, zellon all are organic solvent or the Chemicals of using always.But these halohydrocarbon mostly are toxic substance greatly, and particularly their high volatile volatiles of having threaten very big to environment and human health.China's " hazardous substance file store in the burst Pollution accident " has included 1361 kinds of hazardous and noxious substances, wherein has 68 kinds to be listed in priority pollutant, has 10 kinds to be halohydrocarbon in these 68 kinds of priority pollutants.Therefore, to halohydrocarbon fast, Sensitive Detection is very necessary when the sudden environmental pollution incident of reply.
At present to the emergent detection method in the scene of halohydrocarbon mainly contain water quality detection pipe method, directly intake sample vapor-phase chromatography, rapid detection pipe method, portable gas chromatography method and gas speed is surveyed pipe (German Dreager company product).But it is too low that these detection methods are not sensitivity, is exactly that sense cycle is oversize, can not satisfy outburst surroundings pollution incident emergency requirement.The common method that detects halohydrocarbon in the laboratory is headspace gas chromatography, chromatogram/mass spectrometry method.These methods analyst processes are very loaded down with trivial details, and sense cycle is long, and is costly, are not suitable for using aspect environment protection.
Chemical sensor is the special sensor that a class is specifically designed to detection, perception chemical substance, be generally used for the particular chemical composition in detected gas or the liquid, and the concentration signal of this chemical ingredients is converted to the curtage signal that can detect, have sensitivity, characteristics fast and accurately.No matter liquid phase or the chemical substance of gas phase or pollution substance, chemical sensor all plays an important role in analyte detection process, and along with chemical sensor development of technology and development, the sensing detection method will replace conventional traditional analysis method gradually, and along with the progress that detects automatic technology, the application of transmitter will be general more and extensive, and usage quantity also can grow with each passing day.
Be used for H at present
2S, NO
X, NH
3, HCN, HF, CO
X, HCl, Cl
2, SO
X, CH
4Report arranged Deng the transmitter of poisonous volatile organic compounds such as toxic and harmful and benzene, toluene, formaldehyde more, the production marketing of existing relevant type of commercial sensor.Yet, also seldom report at the chemical sensor of halohydrocarbon.Based on halohydrocarbon with contain the variation that the platinum complex effect causes the fluorescence spectrum of material, exploitation is at methylene dichloride, trichloromethane, tetracol phenixin, 1,2-ethylene dichloride, 1,1,1-trichloroethane, vinyl trichloride, 1,1,2, the transmitter of halohydrocarbon traces commonly used such as 2-tetrachloroethane, methenyl bromide, rapid detection, and the Demonstration Application by transmitter, but realize the mass production of transmitter, the public safety and the environmental protection cause of serving China.
The title complex of platinum has excellent room temperature luminous performance, and it can addition reaction take place with some gas molecules (as halides) and become tetravalence platinum by divalence platinum, thereby the luminosity of material is changed; Utilize this principle can realize the selectivity of some gas molecule is discerned.Previous stage, domestic and international research mainly concentrates on platiniferous oxygen sensing material [Inorganic Chemistry, 2006,45 (12), 4735; J.Phys.Chem.A 2004,108,3485-34922; Inorganic Chemistry, 2004,43 (12), 3724-3732.].Recently begun the title complex of platinum abroad at sarin [J.Am.Chem.Soc.1998,120,12359], sulfurous gas [Chem.Eur.J.2000,6 (8), 1431], the correlative study of cyanogen bromide sensing aspects such as [J.Am.Chem.Soc.2006,128,16641-16648].According to the literature, at present the shortcoming of the small molecules title complex sensing material of platinum is: sensitivity is low, poor selectivity and can not independent film forming, has seriously hindered the application of platinum complex aspect the chemical substance sensing.
Summary of the invention
The object of the present invention is to provide a kind ofly has the luminescent material, method of sensing function and in the application of halohydrocarbon context of detection to halohydrocarbon.Hyperbranched conjugated polymer sensor material based on platinum has following advantage:.
Present method utilizes the title complex at platinum center as sensing material, interact by the coordination between the sensing material of halohydrocarbon and excited state, cause the rapid cancellation of the fluorescence of sensing material,, can realize identification halohydrocarbon by detecting the fluorescence intensity of sensing material.Swager[J.Am.Chem.Soc.2006,128,16641] etc. the halohydrocarbon sensing material of present bibliographical information only has response to BrCN gas, and can not independent film forming; Steven C.F.Kui[J.Am.Chem.Soc.2006,128,8297-8309] etc. report phosphorous title complex except that with the halohydrocarbon effect, also interaction is arranged with ethyl acetate, ether, tetrahydrofuran (THF), acetone, dithiocarbonic anhydride, Skellysolve A, selectivity is relatively poor.
The luminescent material of sensing function provided by the present invention is a kind of organic coordination compound of platinum, it is characterized in that by on the phenyl base, introducing aromatic yl group, make sensing material have the extinction ability of very strong UV-light on the one hand, make sensing material that good film-forming properties is arranged on the other hand, in addition, the most important is the suitable electron donation of aryl, makes that the energy level of title complex is favourable to selectivity, and will help improving the selectivity of material to different halohydrocarbon from molecular conformation analysis.Therefore, sensing material of the present invention had both had good film-forming properties, again halogenated hydrocarbon gas was had good selectivity and high sensitivity simultaneously.The sensing material at platinum provided by the invention center also has the characteristics of synthetic simple and easy large-scale production, for the exploitation of the halohydrocarbon transmitter of practicability is laid a good foundation.Simultaneously, the luminescent material with sensing function provided by the invention can also be used for electroluminescent, photovoltaic cell, chemistry and field of biosensors.
Specifically the present invention at first the invention provides a kind of luminescent material with sensing function of effective detection volatility halohydrocarbon.
The chemical structure of general formula of luminescent material provided by the present invention is shown in Fig. 1, Ar is the aryl of aryl or replacement in the formula, the center is a divalence platinum, with two parts of platinum coordinate be the 2-phenylpyridine, the substituting group that has aryl on the phenyl, wherein the site that links to each other with phenyl of aryl can be 2,3 of a phenyl, 4 or 5, mode of connection also can be singly-bound, two key and triple bond.
This shows, the described luminescent material with the platinum center with sensing function comprises the chemical structural formula of aryl on platinum, 2-phenylpyridine and the phenyl or oligomer that further is built into by aryl and polymkeric substance as (shown in Figure 2), and wherein aryl can be three arylamine, diaryl-amine, carbazole, pyrroles, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, indole carbazole, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, triazine, acridine or the thiazole to electronics; N in the chemical structure of general formula is the positive integer of 2-150.
Also comprise on the aryl and can further increase solvability, extinction ability and give the chromophore that is subjected to electronic capability.Here the purpose that adopts different aryl is that the level structure of title complex and molecular conformation are carried out meticulous adjusting, makes it to adapt to the detection of different halohydrocarbon.Described aryl is characterized in that also comprising the derivative of listed aryl.Comprise and contain alkyl, alkoxyl group, alkylthio, fatty amido, carboxyl, sulfonic group, boronate, cyano group, nitro, amino, ammonium, hydrogen atom, chlorine atom, bromine atoms, iodine atom and ester group on the aryl, also comprise three arylamine, diaryl-amine, carbazole and, a kind of among the pyrroles, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, indole carbazole, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, triazine, acridine, thiazole.
The present invention simultaneously also provides a kind of analysing and detecting method that utilizes the fluorescence means based on the volatile halohydrocarbon of detection of described platinum center luminescent material.Exist coordination to interact between the excited state of assay and platinum center luminescent material, coordination interaction itself is selective, the aryl of high extinction ability or the derivative of aryl have improved the sensitivity of analyzing, the selectivity of the material that the steric factor that the conformation of while aryl causes also further improves.Present method need not detected material is carried out pre-treatment, need not to carry out mark, can directly carry out nondestructive testing to the trace assay.Wherein said platinum centered complex luminescent material can also be regulated by changing aryl the selectivity and the sensitivity of specific halohydrocarbon.The sensing of halohydrocarbon changed by the fluorescence intensity that detects luminescent material realize.
The present invention says that the sensing material that provides has following advantage: 1, response is fast; 2, selectivity is good; 3, easy film forming; 4, synthetic easily.
The luminescent material that halohydrocarbon is had the platinum center of sensing function of the present invention, derivative that comprises Fig. 1, Fig. 2 general structure and aryl etc. can be applicable to the detection to volatile halohydrocarbon, and described halohydrocarbon is chloroform, methylene dichloride, tetracol phenixin, ethylene dichloride, trichloroethane, tetrachloroethane, methenyl bromide or zellon.For example:
Compound 1 synthetic sees embodiment 1, and visible sensing material of the present invention also has easy high yield synthetic characteristics, and the synthetic method of the compound of other aryl is synthetic with compound 1, and productive rate is between 60～90%.
Fig. 4 has provided the tetrahydrofuran solution of compound 1 and the absorption and the fluorescence spectrum of spin-coated thin film, in the specific absorption solution of its film red shift about 10 nanometers, fluorescence than blue shift in the solution about 5 nanometers, its emission peak positions is in 405 nanometers, with it is all response curves of sensing material, being excitation wavelength is 354 nanometers, and emission wavelength is that fluorescence intensity is to the response curve of time under the 405 nanometer conditions.
With compound 1 is example, investigated 1 with the interaction of chloroform, specifically see embodiment 2.In its film chloroform saturated vapo(u)r at room temperature in 200 seconds fluorescence be at present based on the sensitive material of fluoroscopic examination by fully cancellation [Fig. 7].
Adopt compound 1 can effectively discern methenyl bromide as the transmitter of sensing material as embodiment 3, concrete fluorescence spectrum cancellation curve as shown in Figure 8.As can be seen in 100 seconds time, the fluorescence intensity of compound 1 by cancellation 57%.
Can be to 1 as embodiment 4 employing compounds 1 as the transmitter of sensing material, the 2-ethylene dichloride is effectively discerned, and concrete fluorescence spectrum cancellation curve is as shown in Figure 9.Its fluorescence response is different with chloroform and tetrachloroethane as can be seen, and fluorescence strengthened earlier in preceding 6 seconds, fluorescent quenching after this, in 100 seconds time, its fluorescence intensity by cancellation 20%.
Adopt compound 1 can effectively discern sym.-tetrachloroethane as the transmitter of sensing material as embodiment 5, concrete fluorescence spectrum cancellation curve as shown in Figure 8.As can be seen in 100 seconds time, the fluorescence intensity of compound 1 by cancellation 70%.
Adopt compound 1 can effectively discern zellon as the transmitter of sensing material as embodiment 6, concrete fluorescence spectrum cancellation curve as shown in figure 10.Its fluorescence response is different with other halohydrocarbon as can be seen, and it is about 28% that its fluorescence has strengthened earlier in preceding 40 seconds, fluorescent quenching after this, in 150 seconds time, its fluorescence intensity by cancellation 10%.
It is sensing material that embodiment 8 adopts compound 2, has studied the interaction curve of its film and chloroform, the results are shown in Figure 11.In 180 seconds, the fluorescence maximum value of compound 2 has descended about 95%.In 50 seconds cancellation more than 80%.
It is sensing material that embodiment 9 adopts compound 2, has studied the interaction curve of its film and sym.-tetrachloroethane, the results are shown in Figure 12.In 180 seconds, the fluorescence maximum value of compound 2 has descended about 80%.In 100 seconds, the compound 2 frequently cancellation degree of compound 1 has improved 50%.
It is sensing material that embodiment 11 adopts compound 3, has studied the interaction curve of its film and methylene dichloride, the results are shown in Figure 13.In 20 second second, the fluorescence maximum value of compound 3 has descended about 95%.
It is sensing material that embodiment 12 adopts compound 3, has studied the interaction curve of its film and chloroform, the results are shown in Figure 14.In 180 seconds, the fluorescence maximum value of compound 3 has descended about 50%.In 100 seconds, the compound 2 frequently cancellation degree of compound 1 has improved 50%.In 60 second second, the fluorescence of compound 3 cancellation about 40%.
It is sensing material that embodiment 13 adopts compound 3, has studied the interaction curve of its film and tetracol phenixin, the results are shown in Figure 15.In 60 seconds, the fluorescence maximum value of compound 3 has descended about 65%, after this reaches capacity.
Although describe the present invention in conjunction with preference, but the present invention is not limited to the foregoing description, should be understood to, claims have been summarized scope of the present invention, under the guiding of the present invention's design, those skilled in the art will realize that certain change that the various embodiments of the present invention scheme is carried out, all will be covered by the spirit and scope of claims of the present invention.
Description of drawings
Fig. 1. the platinum that halohydrocarbon is had a sensing function provided by the invention is the chemical structure of general formula of the luminescent material at center, and Ar is the aryl of aryl and replacement.
Fig. 2. the oligomer of halohydrocarbon sensing material and the general structure of polymkeric substance.
Fig. 3. the chemical structure of compound 1-3.
Fig. 4. the tetrahydrofuran solution of compound 1 and the absorption of film and fluorescence spectrum.
Fig. 5. the tetrahydrofuran solution of compound 2 and the absorption of film and fluorescence spectrum.
Fig. 6. the absorption of the film of compound 3 and fluorescence spectrum.
Fig. 7. the interaction of compound 1 and chloroform, wherein, (a) for over time in the fluorescence intensity that does not have 420 nanometers of sensing material under the condition of chloroform; (b) be fluorescence intensity that 420 nanometers of sensing material under the chloroform condition are arranged curve over time.
Fig. 8. compound 1 respectively with the interaction of sym.-tetrachloroethane and methenyl bromide.
Fig. 9. compound 1 and 1, the interaction of 2-ethylene dichloride.
Figure 10. the interaction of compound 1 and zellon.
Figure 11. the interaction of compound 2 and chloroform.
Figure 12. the interaction of compound 2 and sym.-tetrachloroethane.
Figure 13. the interaction of compound 3 and methylene dichloride.
Figure 14. the interaction of compound 3 and chloroform.
Figure 15. the interaction of compound 3 and tetracol phenixin.
Embodiment
Below in conjunction with the drawings and specific embodiments the present invention is further described, will helps the understanding of the present invention.But can not limit interest field of the present invention with this, and interest field of the present invention should be with being as the criterion that claims are set forth.
Embodiment 1 (synthesizing of compound 1)
(0.9g 5.6mmol) is dissolved in ether to 2-triphenylamine yl pyridines, and (6.56mL 11.2mmol), reacted 30 minutes the t-Buli of dropping 1.6M under-78 ℃.Still under-78 ℃, drip PtCl again
2(Et
2S)
2(behind the stirring reaction 30min, temperature of reaction system rises to 0 ℃ for 0.5g, diethyl ether solution 1.12mmol).Organic phase is washed with saturated common salt, dichloromethane extraction, dried over mgso.Remove organic solvent, column chromatography is separated, and gets the white object compound, and productive rate is 85%.The structural formula of compound of gained is shown among Fig. 31.
With 1 milliliter of CHCl
3Drip on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 1 film, monitors its wavelength and changes in time at 420 nanometers fluorescent signals, its fluorescence curve time response such as Fig. 7.
The interaction of embodiment 3 compounds 1 and methenyl bromide
1 milliliter of methenyl bromide is dripped on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 1 film, monitor its wavelength and change in time, its fluorescence curve time response such as Fig. 8 at 420 nanometers fluorescent signals.
With 1 milliliter 1, the 2-ethylene dichloride drips on the absorbent cotton, places the fluorescence pond of sealing, clean absorbent cotton of upper cover, the quartz plate of surface coated compound 1 film is inserted, monitor its wavelength and change in time, its fluorescence curve time response such as Fig. 9 at 420 nanometers fluorescent signals.
The interaction of embodiment 5 compounds 1 and sym.-tetrachloroethane
With 1 milliliter 1,1,2, the 2-tetrachloroethane drips on the absorbent cotton, places the fluorescence pond of sealing, clean absorbent cotton of upper cover, the quartz plate of surface coated compound 1 film is inserted, monitor its wavelength and change in time, its fluorescence curve time response such as Fig. 8 at 420 nanometers fluorescent signals.
The interaction of embodiment 6 compounds 1 and zellon
1 milliliter of zellon is dripped on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 1 film, monitor its wavelength and change in time, its fluorescence curve time response such as Figure 10 at 420 nanometers fluorescent signals.
Embodiment 6 (synthesizing of compound 2)
Under the stirring at room condition, (0.2g 0.24mmol) is dissolved in the 20mL tetrahydrofuran (THF) to compound 1.(stirring reaction spends the night Dropwise 5 mL NBS for 0.19g, tetrahydrofuran solution 1.07mmol) in this solution.Steam solvent, add methylene dichloride 150mL, successively with saturated sodium bicarbonate aqueous solution, water and saturated common salt washing, anhydrous MgSO
4Dry.Remove and desolvate, residue separates with silica gel column chromatography, gets white solid 0.24g, productive rate 86.9%.The chemical structural formula of prepared compound 2 is shown among Fig. 32.
The interaction of embodiment 7 compounds 2 and chloroform
1 milliliter of chloroform is dripped on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 1 film, monitor its wavelength and change in time, its fluorescence curve time response such as Figure 11 at 393 nanometers fluorescent signals.
The interaction of embodiment 8 compounds 2 and sym.-tetrachloroethane
With 1 milliliter 1,1,2, the 2-tetrachloroethane drips on the absorbent cotton, places the fluorescence pond of sealing, clean absorbent cotton of upper cover, the quartz plate of surface coated compound 1 film is inserted, monitor its wavelength and change in time, its fluorescence curve time response such as Figure 12 at 393 nanometers fluorescent signals.
Embodiment 9 (synthesizing of compound 3)
Under Ar protection atmosphere, in two mouthfuls of flasks of 50ML, add 0.5g
The 20mL tetrahydrofuran (THF) is stirred to abundant dissolving.System is cooled to-78 ℃, injects the tert-butyl lithium solution of 2.3mL1.6M, continues to keep low temperature, continues reaction 1 hour.Injection is dissolved in the trans-PtCl of 5mL
2(Et
2S)
2(0.24g) tetrahydrofuran solution makes temperature return back to room temperature naturally, stopped reaction behind the continuation reaction 12h.Use 80mL pure water and saturated common salt water washing successively, use 60mL dichloromethane extraction three times, MgSO
4Dry, decompressing and extracting.Column chromatography separate pure product 58mg, productive rate is 14.5%.The structural formula of prepared compound 2 is shown among Fig. 33.
The interaction of embodiment 10 compounds 3 and methylene dichloride
1 milliliter of methylene dichloride is dripped on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 3 films, monitor its wavelength and change in time, its fluorescence curve time response such as Figure 13 at 480 nanometers fluorescent signals.
The interaction of embodiment 11 compounds 3 and chloroform
1 milliliter of chloroform is dripped on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 3 films, monitor its wavelength and change in time, its fluorescence curve time response such as Figure 14 at 480 nanometers fluorescent signals.
The interaction of embodiment 12 compounds 3 and tetracol phenixin
1 milliliter of tetracol phenixin is dripped on the absorbent cotton, place the fluorescence pond of sealing, clean absorbent cotton of upper cover is inserted the quartz plate of surface coated compound 3 films, monitor its wavelength and change in time, its fluorescence curve time response such as Figure 15 at 480 nanometers fluorescent signals.
Claims (10)
1, a kind of have the luminescent material at the platinum center of sensing function to halohydrocarbon, it is characterized in that described luminescent material chemical structure of general formula is:
Ar is the aryl of aryl or replacement in the formula, and the center is a divalence platinum, with two parts of platinum coordinate be the 2-phenylpyridine, have the substituting group of aryl on the phenyl.
2, by the described luminescent material of claim 1, it is characterized in that site that aryl links to each other with phenyl is 2,3,4 or 5 of phenyl, mode of connection is singly-bound, two key or triple bond.
3,, it is characterized in that the described oligomer that is built into by aryl or the chemical structural formula of polymkeric substance are by claim 1 or 2 described luminescent materials:
Wherein aryl is three arylamine, diaryl-amine, carbazole, pyrroles, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, indole carbazole, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, triazine, acridine or thiazole to electronics, and n is 2～150 positive integer.
4, by claim 1 or 2 described luminescent materials, it is characterized in that described aryl comprises the derivative of aryl, comprise and contain alkyl, alkoxyl group, alkylthio, fatty amido, carboxyl, sulfonic group, boronate, cyano group, nitro, amino, ammonium, hydrogen atom, chlorine atom, bromine atoms, iodine atom or ester group on the aryl.
5, utilize the detection method of luminescent material as claimed in claim 1 or 2 to halohydrocarbon, it is characterized in that coordination interacts between the excited state of detected material and platinum center luminescent material, utilize the variation of the fluorescence intensity of fluorescence means by detecting luminescent material to realize.
6, utilize the detection method of luminescent material as claimed in claim 3 to halohydrocarbon, it is characterized in that coordination interacts between the excited state of detected material and platinum center luminescent material, utilize the variation of the fluorescence intensity of fluorescence means by detecting luminescent material to realize.
7, utilize the detection method of luminescent material as claimed in claim 4 to halohydrocarbon, it is characterized in that coordination interacts between the excited state of detected material and platinum center luminescent material, utilize the variation of the fluorescence intensity of fluorescence means by detecting luminescent material to realize.
8, press the application of claim 1 or 2 described luminescent materials, it is characterized in that described luminescent material is applied to the detection to volatile halohydrocarbon, described halohydrocarbon is chloroform, methylene dichloride, tetracol phenixin, ethylene dichloride, trichloroethane, tetrachloroethane, methenyl bromide or zellon.
9, press the application of the described luminescent material of claim 3, it is characterized in that described luminescent material is applied to the detection to volatile halohydrocarbon, described halohydrocarbon is chloroform, methylene dichloride, tetracol phenixin, ethylene dichloride, trichloroethane, tetrachloroethane, methenyl bromide or zellon.
10, press the application of the described luminescent material of claim 4, it is characterized in that described luminescent material is applied to the detection to volatile halohydrocarbon, described halohydrocarbon is chloroform, methylene dichloride, tetracol phenixin, ethylene dichloride, trichloroethane, tetrachloroethane, methenyl bromide or zellon.
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| CN101838291A (en) * | 2010-05-28 | 2010-09-22 | 南京邮电大学 | Preparation and application of platinum complex material with aggregated-state induced phosphorescence emission characteristic |
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| CN102297878B (en) * | 2011-05-19 | 2013-07-31 | 浙江清华长三角研究院 | Electronic nose system for rapid detection of pollution of volatile chlorinated hydrocarbons |
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| CN108169189A (en) * | 2017-12-06 | 2018-06-15 | 济南大学 | A kind of response sulfur dioxide/sulfurous acid（Hydrogen）The ratio fluorescent probe of salt |
| CN108169189B (en) * | 2017-12-06 | 2020-07-07 | 济南大学 | Ratiometric fluorescent probe responding to sulfur dioxide/sulfite (hydrogen) salt |
| CN110746442A (en) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | Imidazole spiro-containing compound and application thereof |
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