CN103436252A - Anion fluorescent probe for forming aggregate through anion inducing - Google Patents
Anion fluorescent probe for forming aggregate through anion inducing Download PDFInfo
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- CN103436252A CN103436252A CN2013103354681A CN201310335468A CN103436252A CN 103436252 A CN103436252 A CN 103436252A CN 2013103354681 A CN2013103354681 A CN 2013103354681A CN 201310335468 A CN201310335468 A CN 201310335468A CN 103436252 A CN103436252 A CN 103436252A
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Abstract
The invention discloses an anion fluorescent probe for forming an aggregate through anion inducing. The probe is characterized in that the probe is a hemicyanine plastocyanin hydrogen sulfate radical molecular fluorescent probe, wherein a chemical structural formula of the probe is A-3,4-dihydroxyphenyl vinyl indolium tetrafluoroborate or B-3,4-dihydroxyphenyl vinyl benzene indolium tetrafluoroborate. A synthetic method of the probe comprises the steps that 1), indoline derivative iodonium salt and 3,4-dihydroxy benzaldehyde are mixed at a mole ratio of 1:1, and subjected to lucifugal heating in alcohol, and react for 24h; 2), KBF4 is added, and subjected to backflow for 2h, and anion exchange is performed; and 3), a pure product recrystallized by absolute ethyl alcohol is adopted. The probe has the advantages that a novel thought is provided for detection of tetrahedral ions by using a strategy that an obvious optical signal change is caused by ion inducing aggregation, and the prepared molecular fluorescent probe shows a very strong fluorescent enhancement effect on the detection of hydrogen sulfate radical ions, and can be used for the detection of hydrogen sulfate radical ions in an environmental sample and a chemical simulation biological system.
Description
Technical field
The present invention relates to the anion fluorescent molecular probe in the fluorescence sense detection technique, especially a kind of anion fluorescent probe that forms aggregate of inducing by negatively charged ion.
Background technology
Negatively charged ion has very important effect in vivo, and the DNA that at first has Genetic Function is the biomacromolecule of anionic; Main enzyme substrates and its cofactor are also the biomacromolecules of anionic; Negatively charged ion also occupies very important status in medical science and catalytic field.Simultaneously, negatively charged ion is also closely related with environmental pollution, and due to excessive use chemical fertilizer, phosphate radical excessive in river can cause the current overnutrition, and excessive nitrate radical can produce carcinogenesis.Therefore, no matter from the biology angle, or, from environmental, the detection of negatively charged ion is all vital.
Traditional negatively charged ion detection method is a lot, but the defect such as that most method has is consuming time, sensitivity is low.And the fluorescence analysis based on the fluorescent probe response signal has advantages of that but simple operation, selectivity are high, respond fast, highly sensitive real-time in-situ and detects.In recent years, this technology is in bio-medical analysis, environment and industrial detection, is used widely in the aspects such as nuclear waste analyzing and processing.Yet the design of carrying out the negatively charged ion probe by traditional self compensation principle (self-complementary) is very challenging.This is that the following factor intrinsic by negatively charged ion self determines: 1) ionic radius is large; 2) to the pH sensitivity; 3) geometric configuration complexity etc.These factors have determined that the difficulty of self compensation principle design negatively charged ion probe routinely is very large, and the selectivity of probe is not high.So, find novel, efficient and simple negatively charged ion probe design strategy, especially design the strategy that negatively charged ion to complex construction has the fluorescent probe of highly sensitive, highly selective recognition function and be very important.
This patent is exactly to develop the New Policy of negatively charged ion probe design for defects such as negatively charged ion probe design difficulty are large, selectivity is not strong.Typically, the dyestuff gathering tends to cause strong spectral signal to change, because congregation causes the clustering phenomena of Absorption and emission spectra red shift to be called J-, assemble, this state of aggregation character has been widely used in detecting novel fluorescence and colorimetric chemical sensor, the photosensitizers etc. of chemical substance; In contrast, because congregation causes the clustering phenomena of absorption band blue shift to be called H-, assemble, the aggregate of the type does not have the fluorescence radiation performance usually, thus utilize the H-aggregate optical characteristics design synthetic molecules fluorescent probe successful case seldom.Yet the people such as W ü rthner have reported that in 2006 a kind of fluorescence of H-aggregate of neuter flower cyanines uniformly dyeing material strengthens luminous behavior, referring to: U. R sch, S. Yao, R. Wortmann, F. W ü rthner,
angew. Chem. Int. Ed. 2006,
45, 7026, the luminous behavior of this dyestuff aggregate is to produce because monomer has formed a kind of H-aggregate with slight swing offset, thereby exceeded the conventional behavior that the H-aggregate causes fluorescent quenching.Inspired by this, we pass through the ingehious design to dye structure, and utilize negatively charged ion to induce the strategy that forms aggregate to carry out the anion-selective fluorescent probe of Development of Novel.
Summary of the invention
The object of the invention is to for above-mentioned technical Analysis, a kind of anion fluorescent probe that forms aggregate of inducing by negatively charged ion is provided, the preparation method of such fluorescent probe is simple, cost is low, and have tetrahedron anion sulfate acid hydrogen root selectivity, to detecting, specific negatively charged ion response is fast, selectivity is single-minded and detection sensitivity is high.
Technical scheme of the present invention:
A kind of anion fluorescent probe that forms aggregate of inducing by negatively charged ion, be the blue plain bisulfate ion fluorescence probes of half cyanines, chemical structural formula is A-3,4-dihydroxy phenyl vinyl indoline a tetrafluoro borate or B-3,4-dihydroxy phenyl vinyl benzene diindyl quinoline a tetrafluoro borate, as follows:
A kind of described preparation method who induces the anion fluorescent probe that forms aggregate by negatively charged ion, step is as follows:
1) by indoline derivative thing salt compounded of iodine and 0412, lucifuge in the solvent dehydrated alcohol stirs and reacting by heating, and Heating temperature is oil bath temperature 100
oc, be 24 hours heat-up time;
2) add tetrafluoro boron potassium (KBF
4) and stirring reaction 2 hours, after carrying out anionresin, obtain the reaction solution that contains thick product;
3) above-mentioned reacting liquid filtering is removed to inorganic salt, the liquid phase rotation is steamed, solid product can obtain the blue plain bisulfate ion fluorescence probe sterling of target product half cyanines with the dehydrated alcohol recrystallization.
Described indoline derivative thing salt compounded of iodine is N-methyl-2,3,3 '-tri-methyl indole quinoline salt compounded of iodine or N-ethyl-2,3, and 3 '-Three methyl Benzene diindyl quinoline salt compounded of iodine, wherein the former prepares anion fluorescent probe A, and the latter prepares anion fluorescent probe B.
The mol ratio of described indoline derivative thing salt compounded of iodine and 0412 is 1:1.
The gross weight of described indoline derivative thing salt compounded of iodine and 0412 and the weight ratio of solvent dehydrated alcohol are 1:15-20.
The mol ratio of described indoline derivative thing salt compounded of iodine and tetrafluoro boron potassium is 1:2.
During described recrystallization, the weight ratio of solid product weight and ethanol is 1:5-15.
A kind of described application of inducing the anion fluorescent probe that forms aggregate by negatively charged ion, for to having the detection of tetrahedral negatively charged ion, detection method is: it is 1 * 10 that the molecular probe material formulation of preparation is become to concentration
-2-5 * 10
-3the probe solution of mol/L, be added to probe solution in detected object, makes the concentration of probe remain on 1 * 10
-5-3 * 10
-6mol/L, after mixing, use the optical excitation of 450-500 nm wavelength immediately, measures the emmission spectrum of solution at 580 nm wavelength, determines the content of negatively charged ion according to typical curve.
The detection principle of this anion fluorescent probe:
All contain the hydroxyl of contraposition in probe molecule, between contraposition hydroxyl and negatively charged ion, can utilize hydrogen bond action to carry out good combination; Secondly, probe molecule all contains the two keys of positively charged C=N, be conducive to and negatively charged ion between form a kind of electrostatic interaction; Finally, specific tetrahedron negatively charged ion can be induced probe molecule to assemble and be contained 3,3 in probe molecule
'-dimethyl, the sterically hindered effect of these two methyl has stoped the complete aspectant H-aggregate of formation between probe molecule, but there is the H-aggregate of slight swing offset, thereby make to there is very strong fluorescent signal after probe molecule and specific tetrahedron anion binding.
Advantage of the present invention is: this anion fluorescent probe has tetrahedron anion sulfate acid hydrogen root selectivity, and to detecting, specific negatively charged ion response is fast, selectivity is single-minded and detection sensitivity is high; Its preparation method is simple, cost is low, easy to implement, for the detection with tetrahedral negatively charged ion provides new design synthetic thinking, be that a kind of novel ion induction is assembled and the simple fluorescence molecule recognition strategy of synthetic route.
[accompanying drawing explanation]
Fig. 1 is fluorescence probe materials A standard working curve.
Fig. 2 is fluorescence probe material B standard working curve.
[embodiment]
Embodiment 1:
A kind of anion fluorescent probe that forms aggregate of inducing by negatively charged ion is the blue plain bisulfate ion fluorescence probes of half cyanines
a, compound name is called 3,4-dihydroxy phenyl vinyl indoline a tetrafluoro borate, and its synthetic method is as follows:
Concrete steps are: take the round-bottomed flask that 138 milligrams of 0412s (1.0 mmol) are placed in 50 mL, add
n-methyl-2,3,3-trimethylammonium-317 milligrams, 3H-indoles iodide (1.0 mmol) and 15 mL dehydrated alcohols, oil bath, stirring, 100
ounder C, reaction is 24 hours; Then add 250 milligrams of (2.0 mmol) potassium tetrafluoroborates in flask, react 2 hours.Solution is spin-dried for, 5 mL 1 for solid, the 2-methylene dichloride dissolves, and removes by filter inorganic salt, and the solution obtained is spin-dried for, and solid carries out recrystallization with dehydrated alcohol 10 mL, obtains the blue plain bisulfate ion fluorescence probe of 300 milligrams of black powder shapes, half cyanines
a, productive rate 78%.M.p. 258-260
oc; ESI:m/z [M-BF
4 -]
+: theoretical value: 294.1489, measured value: 294.1490;
1h NMR (DMSO-d
6, 400 MHz), δ (ppm) 1.76(s, 6H), 4.07(s, 3H), 6.93(d,
j=8.0 Hz, 2H), 7.35(d,
j=16.0 Hz, 1H), 7.62-7.56(m,
j=9.2 Hz, 4H), 7.33(d,
j=6.0 Hz, 2H), 8.28(d,
j=16.0 Hz, 1H), 9.38(s, 1H), 10.18(s, 1H);
13c NMR (DMSO-d
6, 100 MHz), δ (ppm) 182.0,155.0,153.4,147.0,143.9,142.60,142.7,129.7,129.5,127.4,126.8,123.6,117.7,116.9,115.4,110.0,52.5,34.9,26.6.Ultimate analysis: with C
19h
20bF
4nO
2cH
2cl
2calculate, theoretical value C 51.54%, and H 4.76%, and N 3.01%; Measured value C 50.66%, H 4.76%, and N 3.95%.
The fluorescence probe material
athe drafting of standard temperature working curve:
By the fluorescence probe material
abeing made into concentration is 5 * 10
-3the ethanol-water solution of mol/L, the volume ratio of alcohol-water is 1:1, keeps in Dark Place standby, for configuring following experimental solutions.
1) by molecular fluorescence optical probe material
abe mixed with 1 * 10
-5the alcohol-water of mol/L (solvent volume is than being 1:1) solution 50 mL.Get respectively 3 mL in white sample bottle, add respectively the PO of 10 equivalents
4 3-, HPO
4 2-, H
2pO
4 -, NO
3 -, SO
4 2-, HSO
4 -, Cl
-, Br
-, F
-, Ac
-negatively charged ion, under ultra violet lamp and in bore hole observation sample bottle, solution colour changes respectively, under 365 nm length ultraviolet rayed, only adds the solution of bisulfate ion to become light blue fluorescence by lavender fluorescence; Under natural light, only add the solution of bisulfate ion just by purple, to become yellow.
2) by molecular fluorescence optical probe material
abe mixed with 1 * 10
-5the alcohol-water of mol/L (solvent volume is than being 1:1) solution 50 mL.Get respectively 3 mL in brown sample bottle, add respectively the PO of 10 equivalents
4 3-, HPO
4 2-, H
2pO
4 -, NO
3 -, SO
4 2-, HSO
4 -, Cl
-, Br
-, F
-, Ac
-negatively charged ion, measure the ultra-violet absorption spectrum changing conditions, only adds the absorption spectrum of bisulfate ion new absorption peak to occur the short wavelength, and long wavelength's absorption peak disappears, and other ion does not all cause the noticeable change of absorption spectrum.
3) by molecular fluorescence optical probe material
abe mixed with 1 * 10
-5the alcohol-water of mol/L (solvent volume is than being 1:1) solution 50 mL.Get respectively 3 mL in brown sample bottle, add respectively the PO of 10 equivalents
4 3-, HPO
4 2-, H
2pO
4 -, NO
3 -, SO
4 2-, HSO
4 -, Cl
-, Br, F
-, Ac
-negatively charged ion, measure the fluorescence spectrum changing conditions, only add the emmission spectrum of bisulfate ion to appear at the remarkable fluorescence enhancing of 580 nm places appearance the short wavelength, and other ion all do not cause the noticeable change of emmission spectrum.
4) add respectively 3 milliliter 1 * 10 in 16 5 milliliters of brown sample bottles
-5the probe material solution of mol/L, then add successively the hydrogen sulfate ion of 0,0.5,1.0,1.5,2.0,2.5,3.0,3.5,4.0,4.5,5.5,6.5,7.5,10.5,15.5,25.5,30 equivalents and mix.Adopt the excitation wavelength of 450-500 nm to excite its fluorescence spectrum of mensuration, then with probe
afluorescent emission intensity (I) at 580 nm places changes maps and obtains standard working curve bisulfate ion concentration.
Fig. 1 is fluorescence probe materials A standard working curve.
The anion fluorescent probe A of preparation is used for having the detection of tetrahedral negatively charged ion, and we have carried out analog detection to the ionized water sample that adds bisulfate ion, operate as follows:
Add 1 * 10 in 2 ml tap waters
-3mol/L
a, make
aconcentration reach 5 * 10
-6mol/L, after mixing, add 3 * 10
-6the HSO of mol/L
4 -ion is also measured its fluorescence spectrum.Detected result shows: measured value corresponding with typical curve 3 * 10
-6the intensity level of mol/L can be corresponding one by one.
Embodiment 2:
A kind of anion fluorescent probe that forms aggregate of inducing by negatively charged ion is the blue plain bisulfate ion fluorescence probes of half cyanines
b, compound name is called 3,4-dihydroxy phenyl vinyl benzene diindyl quinoline a tetrafluoro borate, and its synthetic method is as follows:
Concrete steps are: take the round-bottomed flask that 138 milligrams of 0412s (1.0 mmol) are placed in 50 mL, add
n-ethyl-2,3,3-trimethylammonium-365 milligrams, 3H-benzindole iodide (1.0 mmol) and 5 mL dehydrated alcohols, oil bath, stirring, 100
ounder C, reaction is 24 hours; Then add 250 milligrams of (2.0 mmol) potassium tetrafluoroborates in flask, react 2 hours.Solution is spin-dried for, 5 mL 1 for solid, the 2-methylene dichloride dissolves, and removes by filter inorganic salt, and the solution obtained is spin-dried for, and solid carries out recrystallization with dehydrated alcohol 10 mL, obtains the blue plain bisulfate ion fluorescence probe of 400 milligrams of black powder shapes, half cyanines
b, productive rate 90%.ESI:m/z [M-BF
4 -]
+: theoretical value: 358.1802, measured value: 358.1800;
1h NMR (DMSO-d
6, 400 MHz), δ (ppm) 1.50(t, J=7.0 Hz 3H), 2.01(s, 6H), 4.80-4.75(m,
j=6.4 Hz, 2H) 6.97(d,
j=8.0 Hz, 1H), 7.42(d,
j=16.4 Hz, 1H), 7.67 (d, J=16.4 Hz, 1H), 7.70(t,
j=8.0 Hz, 2H), 8.79(d,
j=8.0 Hz, 1H), 8.08(d,
j=9.2 Hz, 1H), 8.20(d,
j=8.0 Hz, 1H), 8.27(d,
j=9.2 Hz, 1H), 8.41(d,
j=11.8 Hz, 2H), 9.42(s, 1H), 10.64(s, 1H).Ultimate analysis: with C
24h
24bF
4nO
2calculate, theoretical value C 64.74%, and H 5.43%, and N 3.15%; Measured value C 64.58%, H 5.52%, and N 3.28%.
The fluorescence probe material
bthe drafting of standard temperature working curve:
By fluorescence probe material
bbeing made into concentration is 5 * 10
-3the ethanol-water solution of mol/L, the volume ratio of alcohol-water is 1:1, keeps in Dark Place standby, for configuring following experimental solutions.
1) by the fluorescent optics probe material
bbe mixed with 1 * 10
-5the alcohol-water of mol/L (solvent volume is than being 1:1) solution 50 mL.Pipette respectively 3 mL main body solution and be placed in white sample bottle, add respectively the PO of 10 equivalents
4 3-, HPO
4 2-, H
2pO
4 -, NO
3 -, SO
4 2-, HSO
4 -, Cl
-, Br
-, F
-, Ac
-negatively charged ion is observed respectively solution colour in sample bottle and is changed under bore hole and ultra violet lamp, under natural light, only adds the solution of bisulfate ion just to be become orange-yellow by purple; Under 365 nm length ultraviolet rayed, only add the solution of bisulfate ion to become light blue fluorescence by lavender fluorescence.
2) by the fluorescent optics probe material
bbe mixed with 1 * 10
-5the alcohol-water of mol/L (solvent volume is than being 1:1) solution 50 mL.Pipette respectively 3 mL main body solution and be placed in brown sample bottle, add respectively the PO of 10 equivalents
4 3-, HPO
4 2-, H
2pO
4 -, NO
3 -, SO
4 2-, HSO
4 -, Cl
-, Br
-, F
-, Ac
-negatively charged ion, measure the ultra-violet absorption spectrum changing conditions, only add the absorption spectrum of bisulfate ion to occur that at short wavelength 475 nm places new absorption peak and long wavelength's 577 nm place absorption peaks disappear, and other ion all do not cause the noticeable change of absorption spectrum.
3) by the fluorescent optics probe material
bbe mixed with 1 * 10
-5the alcohol-water of mol/L (solvent volume is than being 1:1) solution 50 mL.Get respectively 3 mL in brown sample bottle, add respectively the PO of 10 equivalents
4 3-, HPO
4 2-, H
2pO
4 -, NO
3 -, SO
4 2-, HSO
4 -, Cl
-, Br, F
-, Ac
-negatively charged ion, measure the fluorescence spectrum changing conditions, only add the emmission spectrum of bisulfate ion to occur that at 565 nm places remarkable fluorescence strengthens, and other ion all do not cause the noticeable change of emmission spectrum.
4) add respectively 3 mL 1 * 10 in 18 brown sample bottles of 5 mL
-5the probe material solution of mol/L, then add successively the hydrogen sulfate ion of 0,0.5,1.0,1.5,2.0,2.5,3.0,3.5,4.0,4.5,5.5,6.5,7.5,10.5,15.5,17.5,22.5,25.5,35.0 equivalents and mix.Adopt the excitation wavelength of 475-530 nm to excite its fluorescence spectrum of mensuration, then with probe
bratio vary and bisulfate ion and fluorescence probe in the fluorescent emission intensity (I) at 555 nm and 595 nm places
bmol ratio mapping and obtain standard working curve.
Fig. 2 is fluorescence probe material B standard working curve.
The anion fluorescent probe A of preparation is used for having the detection of tetrahedral negatively charged ion, and we have carried out analog detection to the ionized water sample that adds bisulfate ion, operate as follows:
Add 1 * 10 in 2 ml tap waters
-3mol/L
b, make
bconcentration reach 5 * 10
-6mol/L, after mixing, add 1 * 10
-6the HSO of mol/L
4 -ion is also measured its fluorescence spectrum.Detected result shows: measured value corresponding with typical curve 3 * 10
-6the intensity level of mol/L can be corresponding one by one.
Claims (8)
1. induce the anion fluorescent probe that forms aggregate by negatively charged ion for one kind, it is characterized in that: be the blue plain bisulfate ion fluorescence probes of half cyanines, chemical structural formula is A-3,4-dihydroxy phenyl vinyl indoline a tetrafluoro borate or B-3,4-dihydroxy phenyl vinyl benzene diindyl quinoline a tetrafluoro borate, as follows:
2. a preparation method who induces as claimed in claim 1 the anion fluorescent probe that forms aggregate by negatively charged ion is characterized in that step is as follows:
1) by indoline derivative thing salt compounded of iodine and 0412, lucifuge in the solvent dehydrated alcohol stirs and reacting by heating, and Heating temperature is oil bath temperature 100
oc, be 24 hours heat-up time;
2) add tetrafluoro boron potassium (KBF
4) and stirring reaction 2 hours, after carrying out anionresin, obtain the reaction solution that contains thick product;
3) above-mentioned reacting liquid filtering is removed to inorganic salt, the liquid phase rotation is steamed, solid product can obtain the blue plain bisulfate ion fluorescence probe sterling of target product half cyanines with the dehydrated alcohol recrystallization.
3. induce according to claim 2 the preparation method of the anion fluorescent probe that forms aggregate by negatively charged ion, it is characterized in that: described indoline derivative thing salt compounded of iodine is N-methyl-2,3,3 '-tri-methyl indole quinoline salt compounded of iodine or N-ethyl-2,3,3 '-Three methyl Benzene diindyl quinoline salt compounded of iodine, wherein the former prepares anion fluorescent probe A, and the latter prepares anion fluorescent probe B.
4. induce according to claim 2 the preparation method of the anion fluorescent probe that forms aggregate by negatively charged ion, it is characterized in that: the mol ratio of described indoline derivative thing salt compounded of iodine and 0412 is 1:1.
5. induce according to claim 2 the preparation method of the anion fluorescent probe that forms aggregate by negatively charged ion, it is characterized in that: the gross weight of described indoline derivative thing salt compounded of iodine and 0412 and the weight ratio of solvent dehydrated alcohol are 1:15-20.
6. induce according to claim 2 the preparation method of the anion fluorescent probe that forms aggregate by negatively charged ion, it is characterized in that: the mol ratio of described indoline derivative thing salt compounded of iodine and tetrafluoro boron potassium is 1:2.
7. induce according to claim 2 the preparation method of the anion fluorescent probe that forms aggregate by negatively charged ion, it is characterized in that: during described recrystallization, the weight ratio of solid product weight and ethanol is 1:5-15.
8. an application of inducing as claimed in claim 1 the anion fluorescent probe that forms aggregate by negatively charged ion, it is characterized in that: for to having the detection of tetrahedral negatively charged ion, detection method is: it is 1 * 10 that the molecular probe material formulation of preparation is become to concentration
-2-5 * 10
-3the probe solution of mol/L, be added to probe solution in detected object, makes the concentration of probe remain on 1 * 10
-5-3 * 10
-6mol/L, after mixing, use the optical excitation of 450-500 nm wavelength immediately, measures the emmission spectrum of solution at 580 nm wavelength, determines the content of negatively charged ion according to typical curve.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693591A (en) * | 2016-03-14 | 2016-06-22 | 上海师范大学 | Ratiometric pH fluorescent probe as well as preparation method and application thereof |
| CN106518749A (en) * | 2016-11-07 | 2017-03-22 | 湖南师范大学 | Rate type difunctional fluorescence molecular probe for detecting HSO4- ions, SO2 and derivatives thereof |
| CN109856104A (en) * | 2019-04-15 | 2019-06-07 | 齐齐哈尔大学 | A kind of half cyanines derivative pH fluorescence probe of benzindole and preparation method thereof |
| CN111675645A (en) * | 2020-07-06 | 2020-09-18 | 天津全和诚科技有限责任公司 | Preparation method of pyrrole-cyanine derivative fluorescent probe |
-
2013
- 2013-08-05 CN CN2013103354681A patent/CN103436252A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| JIAJIA CHANG等: "Efficient fluorescent chemosensors for HSO4- based on a strategy of anion-induced rotation-displaced H-aggregates", 《CHEMICAL COMMUNICATIONS》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693591A (en) * | 2016-03-14 | 2016-06-22 | 上海师范大学 | Ratiometric pH fluorescent probe as well as preparation method and application thereof |
| CN105693591B (en) * | 2016-03-14 | 2019-03-01 | 上海师范大学 | A kind of Ratio-type pH fluorescence probe and the preparation method and application thereof |
| CN106518749A (en) * | 2016-11-07 | 2017-03-22 | 湖南师范大学 | Rate type difunctional fluorescence molecular probe for detecting HSO4- ions, SO2 and derivatives thereof |
| CN109856104A (en) * | 2019-04-15 | 2019-06-07 | 齐齐哈尔大学 | A kind of half cyanines derivative pH fluorescence probe of benzindole and preparation method thereof |
| CN111675645A (en) * | 2020-07-06 | 2020-09-18 | 天津全和诚科技有限责任公司 | Preparation method of pyrrole-cyanine derivative fluorescent probe |
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Application publication date: 20131211 |