CN103232592A - Preparation of conjugated polymer based signal launch type mercury ion optical probe - Google Patents
Preparation of conjugated polymer based signal launch type mercury ion optical probe Download PDFInfo
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- CN103232592A CN103232592A CN2013101119579A CN201310111957A CN103232592A CN 103232592 A CN103232592 A CN 103232592A CN 2013101119579 A CN2013101119579 A CN 2013101119579A CN 201310111957 A CN201310111957 A CN 201310111957A CN 103232592 A CN103232592 A CN 103232592A
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Abstract
The invention relates to preparation and application of a signal launch type mercury ion optical probe based on an arylamine/carbazole containing fluorescent polymer. According to the detection principle of the polymer, the specific action between N-containing atomic primitives and iodine ions is utilized, and by adding iodine ions, a fluorescence quenched polymer-iodine ion compounded system can be obtained. Further, the strong complexing action between mercury ions and iodine ions is utilized to make iodine ions withdrawn from the polymer-iodine ion system so as to realize signal launch for detecting mercury ions. By means of simple aftertreatment, mercury ion detection test paper based on the polymer can be prepared, and by compounding with an inorganic magnetic nano-material, a fluorescent nano-composite sensor that can realize probe recycling through magnetic separation can be prepared. Relevant sensors based on the fluorescent polymer can realize high selectivity and high sensitivity detection on mercury ions, and can reach a naked eye recognition effect.
Description
Technical field
The present invention relates to based on the fluorescent optical sensor that contains arylamine/carbazole conjugated polymers, and relevant colour developing test paper and the difunctional nano composite material of fluorescence-magnetic methods involving and the application that detect with the unblanking type that realizes mercury ion.
Background technology
Mercury ion is that human body and environment are had one of heavy metal element of very big threat and toxic action, develops the method that effectively detects mercury ion fast and has very important practical sense.Method based on fluoroscopic examination has obtained to develop rapidly in recent years, the good and economic environmental protection of effective, highly sensitive, selectivity fast of these class methods, a lot of defectives of traditional detection method before having remedied.But the optical probe molecule that up to the present is used for mercury ion detecting mostly is the fluorescent small molecule material greatly.Compared to the small molecules fluorescent chemicals, the distinctive signal scale effect of fluorescent conjugated polymer can further improve detection sensitivity.So far the most methods of being reported based on conjugated polymers detection mercury ion is the mode of fluorescent signal cancellation, and the relevant report that the mode that strengthens by fluorescent signal detects is also less.
Wu Shuizhu (B. L. Ma, F. Zeng, F. Y. Zheng and S. Z. Wu,
Chem. Eur. J., 2011,
17, 14844-14850) and people such as Huang Wei (Z. Y. Zhang, Q. L. Fan, P. F. Sun, L. L. Liu, X. M. Lu, B. Li, Y. W. Quan and W. Huang,
Macromol. Rapid Commun.,2010,
31, 2160-2165), reported once that the strong complexing action of utilizing between iodide ion and the mercury ion realized the fluoroscopic examination of mercury or iodide ion.S. Valiyaveettil(M. Vetrichelvan, R. Nagarajan and S. Valiyaveettil,
Macromolecules, 2006,
39, 8303-8310) with people such as Zhang Ming (Y. Zhao, L. Yao, M. Zhang and Y. G. Ma,
Talanta, 2012,
97, 343-348), reported once that the conjugated polymers that contains the carbazoles structure can realize the fluoroscopic examination to iodide ion.Utilize carbazole/arylamine class conjugated polymers-iodide ion compound system to realize the methods involving of mercury ion detecting is also used at present.
In order to expand the range of application of detection technique of fluorescence, people have prepared miscellaneous fluorescence nano composite material in recent years.The difunctional nano composite material of fluorescence-magnetic is wherein to develop direction more rapidly, and this type of material can be applicable to technology such as magnetic separation technique, bio-imaging technology, medicament transport technology, cancer cells detection and treatment.The relevant trial that at present this type of fluorescence-magnetic nanometer composite material is used for the detection of mercury ion yet there are no report.Fluorescent conjugated polymer and the magnetic Nano material that will have excellent photochemical stability are compound, by magnetic separation technique easy and simple to handle, can realize the recycling to probe material easily, thereby can further reduce the use cost of probe molecule.
The present invention combines with technology such as nano material and detection test paper by the detection method that the fluorescent conjugated polymer with arylamine/carbazoles structure is used for mercury ion, can realize the quick instantaneity of mercury ion is detected.
Summary of the invention
Technical problem: the objective of the invention is to develop and have arylamine/the fluorescent conjugated polymer sensor of carbazoles structure, and relevant fluorescence magnetic nano composite material and color developing detection test paper and relevant mercury ion detecting technology, this type of probe has highly sensitive, highly selective, reusability and can realize the effect of mercury ion bore hole identification.
Technical scheme: the fluorescence chemical sensor that the present invention is used for mercury ion detecting specifically is based on has arylamine/conjugated polymers of carbazoles structure, and the structure of this base polymer comprises
A, B, C, DFour parts, its general formula are as shown in the formula expression:
The total molar ratio of each component in polymers is n
1+ n
2+ n
3+ n
4=1;
Wherein, (1)
AStructure is the arylamine/carbazole structure class component that contains non-polar group, has following one or more structures:
Polyarylamine:
, R wherein
1, R
2, R
3Can be one or more H, halogen atom, C
1-C
20Alkyl (alkoxyl group), C
2-C
20Haloalkyl, nitro, cyano group, amide group, ketone group, phosphinyl, phosphate-based, sulfonate group, the single replacement or polysubstituted aryl/heterocyclic aryl etc.; M=1,2; N=1,2,3
Polycarbazole:
, R wherein
1Can be one or more H, C
1-C
20Alkyl, alkoxyl group etc.; N=1,2,3
(2)
BStructure is the arylamine/carbazole structure class component that contains polarity or ionic group, has following one or more structures:
Polyarylamine:
, R wherein
1, R
2, R
3Can be the alkyl of above-mentioned polarity or ionic group or alkoxyl group etc. for one or more hydroxyls, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt and end; M=1,2; N=1,2,3
Polycarbazole:
, R wherein
1Can be for can being the alkyl of above-mentioned polarity or ionic group or alkoxyl group etc. for one or more hydroxyls, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt and end; N=1,2,3
(3)
CComponent is for having following one or more structures:
Poly-fluorenes:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
The p-phenylene vinylene:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
Polyparaphenylene's acetylene:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
Poly-to benzene:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
The poly-benzene of SPIRO-:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
(4)
DFor side chain contains the conjugation group of arylamine/carbazole structure, its side-chain structure is following one or more structures:
The arylamine class formation:
, R wherein
1, R
2, R
3Can be one or more H, C
1-C
20Alkyl, alkoxyl group etc.;
The carbazoles structure:
, R wherein
1Can be one or more H, C
1-C
20Alkyl, alkoxyl group etc.
Above-mentioned conjugated polymers its preparation method with arylamine/carbazoles structure has comprised 2 basic steps:
1. prepare and have
A, B, C, DThe monomer of four kinds of chemical structures;
2. according to a certain ratio, synthesize the phase emergencing copolymer by metal catalyzed coupling reaction.
For detection of the colour developing identification test paper of mercury ion, its preparation basic step is as described below:
1. make the organic/aqueous solution of the conjugated polymers that contains arylamine/carbazole primitive;
2. the qualitative filter paper bar is immersed the solution of preparing;
3. the filter paper bar being placed shady and cool place dries.
For detection of the fluorescence-magnetic nanometer composite material of mercury ion, its preparation comprises following 6 basic steps:
1. the matrix propping material is coated to the magnetic Nano microsphere surface, again fluorescent polymer is coated on it;
2. fluorescent polymer directly is coated to the magnetic Nano microsphere surface;
3. magnetic Nano microsphere directly is coated to the fluorescent polymer surface;
4. fluorescent polymer and magnetic Nano microsphere blend are coated to matrix propping material surface;
5. fluorescent polymer and magnetic Nano microsphere blend are coated in the matrix propping material;
6. fluorescent polymer and the blend of matrix propping material are coated to the magnetic Nano microsphere surface.
Technological merit:
1. the conjugated polymers that contains arylamine/carbazoles structure is to implement detection to mercury ion in the mode that fluorescent signal strengthens open type;
2. the required supplementary material of using is abundant for the source in the testing process, iodide ion with low cost.
3. colourless under the conjugated polymers solution state, solution colour is deepened and fluorescent quenching behind the adding iodide ion, and color shoals and the fluorescence answer behind the adding mercury ion, can pass through fluorescence, the detection of bore hole dual mode;
4. colour developing identification test paper is easy to use, can be directly used in the mercury ion that detects in the aqueous solution;
5. the fluorescence magnetic nano material can realize magnetic recovery, repeatedly recycles and keeps better detecting performance;
6. all have higher detection sensitivity and detection speed fast based on the polynary probe system of above-mentioned polymkeric substance.
Description of drawings
Fig. 1. among the embodiment 4, along with the adding of the iodide ion aqueous solution, contain the fluorescence emission spectrum titration figure of conjugated polymers in tetrahydrofuran solution of arylamine class formation.
Fig. 2. among the embodiment 4, along with the adding of the mercury ion aqueous solution, contain the fluorescence emission spectrum titration figure of conjugated polymers in tetrahydrofuran solution of arylamine class formation.
Fig. 3. among the embodiment 5, contain the conjugated polymers (tetrahydrofuran solution) of arylamine class formation to selectivity and the freedom from jamming fluorescence emission spectrogram of various public metal ions (aqueous solution).
Fig. 4. among the embodiment 6, contain the conjugated polymers (tetrahydrofuran solution) of arylamine class formation to the bore hole identification figure (picture has carried out gray scale to be handled) of each metal ion species (aqueous solution).
Fig. 5. among the embodiment 7, the fluorescent emission intensity variation diagram when adding the iodide ion aqueous solution and the mercury ion aqueous solution successively in the tetrahydrofuran (THF) dispersion liquid of fluorescence magnetic nano material.
Fig. 6. the constitutional features figure of fluorescence-magnetic nanometer composite material.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention is not limited to following examples.
Take by weighing 9,9 – Er Xin Ji –, 2,7 – hypoboric acid ester fluorenes (0.321 gram, 0.5 mmole),
N,
N– two (4 – bromobenzene) – 4 – (phenylacetylene) amine (0.252 gram, 0.5 mmole), 3 milligrams of palladium, 6 milligrams of thricyclohexyl phosphorus, 3 tri-n-octyl methyl ammonium chlorides add 10 milliliters of toluene behind the feeding nitrogen, 20% solution of potassium carbonate is reflected under the nitrogen protection and refluxed 3 days; Cool to room temperature, with reactant concentrate, reprecipitation, filtration, silica gel chromatography purifying, reconcentration, 50 in methyl alcohol
oObtain solid product after the C vacuum-drying.
Take by weighing 9,9 – Er Xin Ji – 2,7 – hypoboric acid ester fluorenes (0.321 gram, 0.5 mmole), 9 – (4 – (3 – (4 – p-methoxy-phenyl) quinoxalinyl) phenyl) – 3,6 – dibromo carbazoles (0.1905 gram, 0.3 mmole), 3,6 – Er Xiu –, 9 – (4 – triisopropyl silicon phenylacetylene base) carbazole (0.1905 gram, 0.2 mmole), 3 milligrams of palladium, 6 milligrams of thricyclohexyl phosphorus, 3 tri-n-octyl methyl ammonium chlorides, add 10 milliliters of toluene after feeding nitrogen, 20% solution of potassium carbonate is reflected under the nitrogen protection and refluxed 3 days; Cool to room temperature, with reactant concentrate, reprecipitation, filtration, silica gel chromatography purifying, reconcentration, 50 in methyl alcohol
oObtain solid product after the C vacuum-drying;
The above-mentioned solid that obtains is dissolved in 10 milliliters of tetrahydrofuran (THF)s, adds 0.9 milliliter of tetrabutyl ammonium fluoride, under nitrogen protection, refluxed 1 day; Cool to room temperature then, with reactant concentrate, reprecipitation, filtration, silica gel chromatography purifying, reconcentration, 50 in methyl alcohol
oObtain solid product after the C vacuum-drying.
The preparation of embodiment 3, fluorescence-magnetic nanometer composite material:
The ferriferrous oxide nano microballoon (5 milligrams) of the coated with silica that the nitrine that prepared is modified, the conjugated polymers (5 milligrams) that contains the carbazoles structure, join in 100 milliliters of three-necked bottles, feed nitrogen and add 5 milligram of three (triphenyl phosphorus) cuprous bromide again, 10 milliliters of tetrahydrofuran (THF)s, ultrasonic 20 minutes, 40
oUnder the C, mechanical stirring is spent the night; Reactant tetrahydrofuran (THF) ultrasonic cleaning 3 times, 50
oObtain solid product after the C vacuum-drying.
To contain the conjugated polymers configuration of arylamine class formation into about 1 * 10
-5The tetrahydrofuran solution of M pipettes 3 milliliters of solution that prepare in cuvette, adds the iodide ion aqueous solution of progressive concentration in the cuvette, reaches balance until the fluorescent quenching degree; Test data shows the adding along with iodide ion, and the emission peak at about 432 nm places weakens (as shown in Figure 1) gradually in the fluorescence emission spectrum of polymkeric substance.Again the mercury ion aqueous solution of progressive concentration is dropped in the above-mentioned solution that reaches balance, reach balance until fluorescence answer degree; Test data shows the adding along with mercury ion, and the emission peak at about 432 nm places strengthens (as shown in Figure 2) gradually in the fluorescence emission spectrum of polymkeric substance, its lowest detectable limit ~ 2.4 * 10
-7M.
The selection interference experiment of embodiment 5, different metal ion:
To contain the conjugated polymers configuration of arylamine class formation into about 1 * 10
-5The tetrahydrofuran solution of M pipettes 3 milliliters of solution that prepare in cuvette, drips 7 microlitres 1 * 10 in cuvette
-1The iodide ion deionized water solution of M reaches balance to the degree of fluorescent quenching, drips 2.5 microlitres 1 * 10 respectively then in cuvette
-3Metal ion (the Cu of M
2+, Co
2+, Mg
2+, Ni
2+, Pb
2+, Sn
2+, Sr
2+, Cd
2+, Ag
+, Ba
2+, Al
3+, Zn
2+, Ca
2+, Fe
3+) aqueous solution, record respectively do not add metal ion and add metal ion and add metal ion after add 2.5 microlitres 1 * 10 again
-3The fluorescence emission spectrum (as shown in Figure 3) of the mercury ion aqueous solution of M; Test data shows to have only that intensity of emission spectra just tangible enhancing can occur when the metal ion that adds is mercury ion, and emmission spectrum does not then have obvious variation when adding other metal ions except mercury ion; Considerable change all appears in emmission spectrum when adding mercury ion again after adding metal ion, illustrates that this fluorescence chemical sensor has higher selectivity and freedom from jamming.
To contain the conjugated polymers configuration of arylamine class formation into about 1 * 10
-5The tetrahydrofuran solution of M immersed the qualitative filter paper bar in the solution 5 minutes afterwards, and taking-up is dried, and drips 7 microlitres 1 * 10 at 15 filter paper respectively
-1The iodide ion deionized water solution of M, whole filter paper bars all become yellow after 5 minutes, drip 2.5 microlitres 1 * 10 respectively on filter paper again
-3Metal ion (the Cu of M
2+, Co
2+, Mg
2+, Ni
2+, Pb
2+, Sn
2+, Sr
2+, Cd
2+, Ag
+, Ba
2+, Al
3+, Zn
2+, Ca
2+, Fe
3+, Hg
2+) aqueous solution, taking pictures then obtains Metal Ion Selective Electrode experiment photo; Photo shows: have only the color of solution when the metal ion that adds is mercury ion to be become colorless by yellow, the color of solution is then less than too big variation (as shown in Figure 4) when adding other metal ions except mercury ion.
With preparing the tetrahydrofuran (THF) dispersion liquid of fluorescence-magnetic Nano material preparation of gained into about 5 mcg/ml, pipette 3 milliliters in cuvette, add 2.31 * 10 successively
-4The iodide ion deionized water solution and 8.25 * 10 of M
-5The mercury ion aqueous solution of M is tested its fluorescence emission spectrum, the intact one group of magnetic recovery cleaning afterwards of every survey, repeated test 10 times.Test data shows, about 418 nm place emission peak strength reductions when adding the iodide ion deionized water solution, about 418 nm place emission peak intensity enhancing (as shown in Figure 5) when adding the mercury ion aqueous solution illustrate that this fluorescence magnetic nano-sensor has good recovery, can reuse.
Claims (6)
1. based on the unblanking type mercury ion optical probe of conjugated polymers, it is characterized in that:
(1) this type of conjugated polymers is the fluorescent conjugated polymer that contains arylamine/carbazoles structural constituent;
(2) the detection principle of this type of conjugated polymers is the specific function between N atom primitive and the iodide ion of containing that utilizes in the polymkeric substance, by adding iodide ion, obtain fluorescence by the polymkeric substance of cancellation-iodide ion compound system, and then utilize strong complexing action between mercury ion and the iodide ion that iodide ion in polymkeric substance-iodide ion system is detached and realize that fluorescent signal opens to detect mercury ion;
(3) based on this type of conjugated polymers, prepare the difunctional nano combined sensor of fluorescence-magnetic that a class fluorescent method detects mercury ion;
(4) based on this type of conjugated polymers, prepare the detection test paper of class colour developing identification mercury ion.
The conjugated polymers that contains arylamine/carbazole structure class component according to claim 1 can by
A, B, C, DFour parts are formed, and have following structure:
The total molar ratio of each component in polymers is n
1+ n
2+ n
3+ n
4=1;
Wherein, (1)
AStructure is the arylamine/carbazole structure class component that contains non-polar group, has following one or more structures:
Polyarylamine:
, R wherein
1, R
2, R
3Can be one or more H, halogen atom, C
1-C
20Alkyl (alkoxyl group), C
2-C
20Haloalkyl, nitro, cyano group, amide group, ketone group, phosphinyl, phosphate-based, sulfonate group, the single replacement or polysubstituted aryl/heterocyclic aryl etc.; M=1,2; N=1,2,3
Polycarbazole:
, R wherein
1Can be one or more H, C
1-C
20Alkyl, alkoxyl group etc.; N=1,2,3
(2)
BStructure is the arylamine/carbazole structure class component that contains polarity or ionic group, has following one or more structures:
Polyarylamine:
, R wherein
1, R
2, R
3Can be the alkyl of above-mentioned polarity or ionic group or alkoxyl group etc. for one or more hydroxyls, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt and end; M=1,2; N=1,2,3
Polycarbazole:
, R wherein
1Can be for can being the alkyl of above-mentioned polarity or ionic group or alkoxyl group etc. for one or more hydroxyls, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt and end; N=1,2,3
(3)
CComponent is for having following one or more structures:
Poly-fluorenes:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
The p-phenylene vinylene:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
Polyparaphenylene's acetylene:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
Poly-to benzene:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and the end alkyl (alkoxyl group) that is hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group etc.; N=1,2,3
The poly-benzene of SPIRO-:
, R wherein
1, R
2Can be one or more H, C
1-C
20Alkyl (alkoxyl group) and end be the alkyl (alkoxyl group) of hydroxyl, polyether, sulfonate, carboxylate salt, phosphoric acid salt, ammonium salt isopolarity or ionic group; N=1,2,3
(4)
DFor side chain contains the conjugation group of arylamine/carbazole structure, its side-chain structure is following one or more structures:
The arylamine class formation:
, R wherein
1, R
2, R
3Can be one or more H, C
1-C
20Alkyl, alkoxyl group etc.;
The carbazoles structure:
, R wherein
1Can be one or more H, C
1-C
20Alkyl, alkoxyl group etc.
3. detect the difunctional nano combined sensor of fluorescence-magnetic of mercury ion according to a kind of fluorescent method described in the claim 1, its constitutional features as shown in Figure 6, the complex method of the nano material of fluorescence magnetic shown in the figure has 6 classes, and wherein the inorganic nano magneticsubstance is: contain iron-based, Ni-based, cobalt-based and alloy thereof; Magnetic such as rare earth alloy, ferritic alloy nano material; The matrix propping material is: but organo-siloxane, the polymkeric substance that contains modification group and organic molecule, polymer dielectric etc.; Fluorescent polymer is the polymkeric substance described in the claim 2.
4. the difunctional nano combined sensor of fluorescence-magnetic that detects for mercury ion fluorescent according to claim 1, it is as follows that it detects step:
(1) dispersion liquid of certain density this nano composite material of preparation;
(2) in dispersion liquid, drip the detection substrate that the iodide ion aqueous solution obtains fluorescent quenching;
(3) in above-mentioned dispersion liquid, drip the mercury ion aqueous solution and its fluorescence Recovery Process is carried out signal tracking again;
(4) the above-mentioned mixed solution of ultrasonic cleaning, the magnetic recovery nano composite material also recycles.
5. the preparation method of the colour developing identification test paper for detection of mercury ion according to claim 1, its characteristics are at first to be mixed with organic fluorescent conjugated polymer described in the claim 2 or the aqueous solution, the qualitative filter paper bar is immersed wherein, be placed into the cool place and locate to dry to get final product.
6. according to the application method of the fluorescence chemical sensor that is used for mercury ion detecting described in the claim 1, it is characterized in that such fluorescence chemical sensor can form the combined probe system with iodide ion and detect for the fluorescent signal open type of mercury ion, and it has stronger immunity from interference to other common metal ions, and can realize bore hole identification and recycle.
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Cited By (3)
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| CN105384917A (en) * | 2015-11-10 | 2016-03-09 | 华南理工大学 | Conjugated polymer with side chain containing sulfonic acid or sulfonate and plane-inverted organic/inorganic hybrid perovskite solar cell prepared from conjugated polymer |
| CN107245334A (en) * | 2017-06-23 | 2017-10-13 | 东华大学 | A kind of water soluble polymer fluoresceins fluorescence probe for detecting mercury ion and preparation method thereof |
| EP3246347A4 (en) * | 2015-01-13 | 2018-08-22 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Conjugated polymer containing ethynyl crosslinking group, mixture, composition, organic electronic device containing the same and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3246347A4 (en) * | 2015-01-13 | 2018-08-22 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Conjugated polymer containing ethynyl crosslinking group, mixture, composition, organic electronic device containing the same and application thereof |
| US10364316B2 (en) | 2015-01-13 | 2019-07-30 | Guangzhou Chinaray Optoelectronics Materials Ltd. | Conjugated polymer containing ethynyl crosslinking group, mixture, formulation, organic electronic device containing the same and application therof |
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| CN107245334A (en) * | 2017-06-23 | 2017-10-13 | 东华大学 | A kind of water soluble polymer fluoresceins fluorescence probe for detecting mercury ion and preparation method thereof |
| CN107245334B (en) * | 2017-06-23 | 2019-05-03 | 东华大学 | A kind of water soluble polymer fluoresceins fluorescence probe and preparation method thereof detecting mercury ion |
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