CN105647514A - Fluorescence probe and preparing method thereof - Google Patents
Fluorescence probe and preparing method thereof Download PDFInfo
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- CN105647514A CN105647514A CN201610027692.8A CN201610027692A CN105647514A CN 105647514 A CN105647514 A CN 105647514A CN 201610027692 A CN201610027692 A CN 201610027692A CN 105647514 A CN105647514 A CN 105647514A
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention discloses a hypochlorous acid fluorescence probe based on carbazole. The structural formula of the hypochlorous acid fluorescence probe is shown in the description. The synthesis process is simple, and the prepared hypochlorous acid fluorescence probe is high in selectivity, high in quantum yield, high in reaction speed, and large in strokes (107 nm). The fluorescence intensity of reaction between the fluorescence probe and hypochlorous acid has a good linear relation with the concentration (0-5 microns) of hypochlorous acid, and limit of detection (0.44 micron) is low.
Description
Technical field
The present invention relates to a kind of fluorescence probe and preparation method thereof, specifically a kind of carbazoles fluorescent dye containing Maleic nitrile amine groups and preparation method thereof, the application of this fluorescent dye in sensor simultaneously and for detection of hypochlorite, belongs to anion fluorescent sensor field.
Technical background
Fluorescent optical sensor refers to can have an effect with analyte to be measured and by the molecular device of changing into the signal form of expression of fluorescence signal. Because it has many merits, the advantage such as for example selectively good, highly sensitive, fast response time, synthesis step be simple, is widely used in a series of fields such as bio-imaging, environmental monitoring. Due to the features such as modification that are easy to simple in structure, study more deeply based on micromolecular fluorescent optical sensor, for life science provides efficient real-time in-situ testing tool.
Summary of the invention
Technical problem to be solved by this invention is: a kind of fluorescence probe and preparation method thereof is provided, the present invention has well selective containing the carbazoles fluorescent optical sensor of Maleic nitrile amine groups, very high sensitivity, very fast response speed, can detect hypochlorous acid by very strong fluorescence simultaneously.
The technical solution used in the present invention is:
A hypochlorous acid fluorescence probe based on carbazole, its structural formula is:
Described a kind of fluorescence probe is for detection of hypochlorous acid.
A preparation method for a kind of fluorescence probe claimed in claim 1, comprises the following steps:
(1) KOH (200mmol, 11.3g) be dissolved in proper amount of acetone, under room temperature, stir 30 minutes, then the 3-iodine carbazole (40mmol with acetone solution, 11.7g) add in above-mentioned solution, under room temperature, stir 4 hours, finally the bromoethane (60mmmol with acetone solution, 4.5mL) add in above-mentioned solution, under room temperature, stir and spend the night. Reaction finishes rear with benzinum: ethyl acetate=15:1 crosses post purification as eluent and obtains compound 1.
(2) get 40mLDMF and put into three-neck flask, in ice-water bath, slowly add POCl3(13.3mL), add rear stirring 30 minutes, more at room temperature react 1 hour. With appropriate 1,2-dichloroethanes dissolved compound 1(23mmol, 7.4g) slowly splash in above-mentioned solution, under room temperature, stir 1 hour, then 95 DEG C of backflows are spent the night. Cooling rear with dichloromethane extraction, anhydrous magnesium sulfate drying, crosses post purification and obtains compound 2.
(3) it is 1: 3: 5 by amount of substance ratio: take compound 2,4-vinylpridine, K at 0.1: 0.32CO3, palladium, tri-o-tolyl phosphine in flask, make solvent with 1-METHYLPYRROLIDONE, under nitrogen protection, 130 DEG C of reactions 2 days. After reaction finishes, filter out catalyst, with dichloromethane extraction, anhydrous magnesium sulfate drying, cross post purification and obtain compound 3.
(4) take 0.16g(0.5mmol) compound 3 is dissolved in acetone, adds 0.062mL(1mmol) iodomethane refluxes and spends the night. Reaction finishes rear cold filtration, then obtains compound 4 for twice by recrystallizing methanol.
(5) by amount of substance than taking compound 4 and 2 for 1:3,3-diaminourea-2-maleonitrile is in round-bottomed flask, methyl alcohol is made solvent, splashes into several glacial acetic acid, refluxes 4 hours at 70 DEG C. Reaction finishes rear cold filtration, then obtains target compound HCCN for twice by recrystallizing methanol.
Beneficial effect body of the present invention is: fluorescent dye prepared by the present invention is synthetic simple, and structure obtains nuclear-magnetism, mass spectrographic sign confirms, has higher fluorescence quantum yield, can be highly sensitive in homogeneous system, highly selective realizes hypochlorous detection.
Brief description of the drawings
Fig. 1 is that described fluorescence probe is to ClO-Ion fluorescence response diagram;
Fig. 2 is that described fluorescence probe is to ClO-Ion ultraviolet response diagram;
Fig. 3 is the fluorescence intensity change figure that the common anion that may disturb, cation and active oxygen disturbs titration;
Fig. 4 is common anion, cation and active oxygen and ClO-The competitiveness fluorescent Strength Changes figure of ion; In figure, 1:ClO-,2:CO3 2-,3:HPO4 2-,4:CN-,5:SO3 2-,6:H2PO4 -,7:HCO3 -,8:AcO-,9:F-,10:Zn2+,11:Hg2+,12:Al3+,13:Mg2+,14:Fe3+,15:Cu2+,16:TBHP,17:H2O2,18:·NO,19:·OH,20:1O2,21:TBO·。
Fig. 5 is the detectability fluorogram of described fluorescence probe;
Fig. 6 is described fluorescence probe and 40 equivalent ClO-The reaction time fluorogram of ion.
Specific embodiment
Synthetic route of the present invention is as follows:
Embodiment 1: synthetic detailed step is as follows:
(1) KOH (200mmol, 11.3g) be dissolved in proper amount of acetone, under room temperature, stir 30 minutes, then the 3-iodine carbazole (40mmol with acetone solution, 11.7g) add in above-mentioned solution, under room temperature, stir 4 hours, finally the bromoethane (60mmmol with acetone solution, 4.5mL) add in above-mentioned solution, under room temperature, stir and spend the night. Reaction finishes rear with benzinum: ethyl acetate=15:1 crosses post purification as eluent and obtains compound 1.
1HNMR(400MHz,CDCl3):δ8.37(s,1H),8.00(d,J=7.8Hz,1H),7.67(d,J=8.5Hz,1H),7.46(t,J=7.7Hz,1H),7.36(d,J=8.2Hz,1H),7.20(d,J=8.0Hz,1H),7.14(d,J=8.6Hz,1H),4.28(q,J=7.2Hz,2H),1.38(t,J=7.2Hz,3H).
13CNMR(100MHz,CDCl3):δ139.91,139.04,133.80,129.27,126.37,125.47,121.68,120.61,119.33,110.53,108.66,81.22,37.62,13.78.
(2) get 40mLDMF and put into three-neck flask, in ice-water bath, slowly add POCl3(13.3mL), add rear stirring 30 minutes, more at room temperature react 1 hour. With appropriate 1,2-dichloroethanes dissolved compound 1(23mmol, 7.4g) slowly splash in above-mentioned solution, under room temperature, stir 1 hour, then 95 DEG C of backflows are spent the night. Cooling rear with dichloromethane extraction, anhydrous magnesium sulfate drying, crosses post purification and obtains compound 2.
1HNMR(400MHz,CDCl3):δ10.08(s,1H),8.53(s,1H),8.45(s,1H),8.03(d,J=8.5Hz,1H),7.78(d,J=8.5Hz,1H),7.47(d,J=8.5Hz,1H),7.24(d,J=8.7Hz,1H),4.37(q,J=7.2Hz,2H),1.45(t,J=7.2Hz,3H).
13CNMR(100MHz,CDCl3):δ191.58,143.40,139.83,134.98,129.68,128.95,127.50,125.48,124.43,121.83,111.14,108.98,82.93,38.08,13.80.
(3) it is 1: 3: 5 by amount of substance ratio: take compound 2,4-vinylpridine, K at 0.1: 0.32CO3, palladium, tri-o-tolyl phosphine in flask, make solvent with 1-METHYLPYRROLIDONE, under nitrogen protection, 130 DEG C of reactions 2 days. After reaction finishes, filter out catalyst, with dichloromethane extraction, anhydrous magnesium sulfate drying, cross post purification and obtain compound3。
1HNMR(400MHz,CDCl3):δ9.97(s,1H),8.50-8.42(m,3H),8.10(s,1H),7.88(d,J=8.5Hz,1H),7.58(d,J=8.5Hz,1H),7.33(d,J=6.2Hz,1H),7.29(d,J=11.6Hz,2H),7.25(d,J=5.1Hz,2H),6.90(d,J=16.3Hz,1H),4.21(q,J=7.1Hz,2H),1.34(t,J=7.2Hz,3H).
13CNMR(100MHz,CDCl3):δ190.54,149.07,143.85,142.85,139.83,132.43,127.76,127.63,126.48,124.78,122.94,122.82,122.40,121.96,119.60,118.54,108.41,107.92,37.01,12.82.
(4) take 0.16g(0.5mmol) compound3Be dissolved in acetone, add 0.062mL(1mmol) iodomethane reflux spend the night. Reaction finishes rear cold filtration, then obtains compound 4 for twice by recrystallizing methanol.
1HNMR(400MHz,DMSO-d 6 ):δ10.11(s,1H),8.84(d,J=6.4Hz,2H),8.79(s,1H),8.76(s,1H),8.25-8.17(m,3H),8.06(d,J=8.5Hz,1H),7.96(d,J=8.6Hz,1H),7.88-7.84(m,2H),7.60(d,J=16.3Hz,1H),4.57(q,J=6.8Hz,2H),4.26(s,3H),1.38(t,J=7.0Hz,3H).
13CNMR(100MHz,DMSO-d 6 ):δ192.35,153.31,145.30,144.13,142.17,142.14,129.33,128.01,127.96,127.82,124.15,123.43,123.38,122.81,121.69,121.30,111.06,110.64,47.24,38.19,14.29.MS(MALDI-TOF):m/z:calcd.forC23H21N2O+:341.1648,found:341.1704.
(5) by amount of substance than taking compound 4 and 2 for 1:3,3-diaminourea-2-maleonitrile is in round-bottomed flask, methyl alcohol is made solvent, splashes into several glacial acetic acid, refluxes 4 hours at 70 DEG C. Reaction finishes rear cold filtration, then obtains a kind of yellow solid for twice by recrystallizing methanol, and productive rate 75%, notes by abridging as HCCN, and structural formula is as follows:
1HNMR(400MHz,DMSO-d 6 ):δ8.86(s,1H),8.82(d,J=6.3Hz,2H),8.62(s,1H),8.44(s,1H),8.27(d,J=8.7Hz,1H),8.24-8.16(m,3H),7.94(d,J=8.2Hz,1H),7.88-7.73(m,4H),7.54(d,J=16.2Hz,1H),4.54(q,J=6.7Hz,2H),4.25(s,3H),1.38(t,J=7.0Hz,3H).
13CNMR(100MHz,DMSO-d 6 ):δ155.78,152.85,144.83,142.20,141.92,141.48,127.67,127.30,127.11,126.77,125.62,122.95,122.93,122.84,122.45,121.20,120.58,114.69,113.91,110.49,110.13,103.44,46.71,37.58,13.86.MS(MALDI-TOF):m/z:calcd.forC27H23N6 +:431.1979,found:431.2549.
Embodiment 2: under solution state (homogeneous phase) to ClO-The detection of ion
As shown in Figure 1, the fluorescence titration curve of described a kind of fluorescence probe, adds ClO-The concentration of ion and fluorescence intensity are good linear relationship, when adding 40 equivalent ClO-When ion, fluorescence intensity reaches the strongest (fluorescence strengthens 17.5 times). Described a kind of fluorescence probe concentration is 1 × 10-5Mol/L, test condition is PBS: acetonitrile=8:2, room temperature condition. Fig. 2 is that described a kind of fluorescence probe is to ClO-Ion ultraviolet response diagram. By Fig. 3, we can see, other ion and active oxygen all do not respond this probe, only ClO-Ion has response, has embodied the selectivity of probe, and other ion and active oxygen are to probe in detecting ClO as seen from Figure 4-Ion does not almost disturb. By the detectability fluorogram of a kind of fluorescence probe described in Fig. 5, the fluorescence intensity of mensuration and ClO-Concentration has good linear relationship. Fig. 6 is described a kind of fluorescence probe and 40 equivalent ClO-The reaction time fluorogram of ion, can see in 2min, and fluorescence intensity has just reached very high value fast, and visible described fluorescence probe is to ClO-Response speed is very fast.
Therefore described a kind of fluorescence probe can detect ClO by fluorescence mode-Ion, excitation wavelength 434nm, slit width is 10nm. Described a kind of fluorescence probe is realized hypochlorous detection as highly sensitive, highly selective.
Claims (4)
1. a fluorescence probe, is characterized in that its structural formula is:
。
2. a kind of fluorescence probe as claimed in claim 1, is characterized in that: for detection of hypochlorous acid.
3. a preparation method for a kind of fluorescence probe claimed in claim 1, is characterized in that comprising the following steps:
(1) KOH (200mmol, 11.3g) be dissolved in proper amount of acetone, under room temperature, stir 30 minutes, then the 3-iodine carbazole (40mmol with acetone solution, 11.7g) add in above-mentioned solution, under room temperature, stir 4 hours, finally the bromoethane (60mmmol with acetone solution, 4.5mL) add in above-mentioned solution, under room temperature, stir and spend the night; Reaction finishes rear with benzinum: ethyl acetate=15:1 crosses post purification as eluent and obtains compound 1;
(2) get 40mLDMF and put into three-neck flask, in ice-water bath, slowly add POCl3(13.3mL), add rear stirring 30 minutes, more at room temperature react 1 hour; With appropriate 1,2-dichloroethanes dissolved compound 1(23mmol, 7.4g) slowly splash in above-mentioned solution, under room temperature, stir 1 hour, then 95 DEG C of backflows are spent the night; Cooling rear with dichloromethane extraction, anhydrous magnesium sulfate drying, crosses post purification and obtains compound 2;
(3) it is 1: 3: 5 by amount of substance ratio: take compound 2,4-vinylpridine, K at 0.1: 0.32CO3, palladium, tri-o-tolyl phosphine in flask, make solvent with 1-METHYLPYRROLIDONE, under nitrogen protection, 130 DEG C of reactions 2 days; After reaction finishes, filter out catalyst, with dichloromethane extraction, anhydrous magnesium sulfate drying, cross post purification and obtain compound 3;
(4) take 0.16g(0.5mmol) compound 3 is dissolved in acetone, adds 0.062mL(1mmol) iodomethane refluxes and spends the night; Reaction finishes rear cold filtration, then obtains compound 4 for twice by recrystallizing methanol;
(5) by amount of substance than taking compound 4 and 2 for 1:3,3-diaminourea-2-maleonitrile is in round-bottomed flask, methyl alcohol is made solvent, splashes into several glacial acetic acid, refluxes 4 hours at 70 DEG C; Reaction finishes rear cold filtration, then obtains target compound HCCN for twice by recrystallizing methanol.
4. the preparation method of a kind of fluorescence probe as claimed in claim 4, it is characterized in that: in step (1), purification by silica gel column chromatography adopts ethyl acetate: benzinum is 1:15, in step (2), purification by silica gel column chromatography adopts ethyl acetate: benzinum is 1:4, and in step (3), purification by silica gel column chromatography adopts ethyl acetate: benzinum is 1:2.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114249740A (en) * | 2021-11-23 | 2022-03-29 | 南京林业大学 | For detecting ClO-Ionic tanshinone benzimidazole type fluorescent probe and preparation method and application thereof |
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| CN104003906A (en) * | 2014-06-11 | 2014-08-27 | 内蒙古民族大学 | Pyrene fluorescence probe and preparation method and application thereof |
| CN104710976A (en) * | 2015-01-06 | 2015-06-17 | 南京工业大学 | Hypochlorite ion fluorescent probe, preparation method and application thereof |
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Patent Citations (3)
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| KR20120011062A (en) * | 2009-05-20 | 2012-02-06 | 가부시키가이샤 아이에이치아이 | Method for producing impeller applied to supercharger |
| CN104003906A (en) * | 2014-06-11 | 2014-08-27 | 内蒙古民族大学 | Pyrene fluorescence probe and preparation method and application thereof |
| CN104710976A (en) * | 2015-01-06 | 2015-06-17 | 南京工业大学 | Hypochlorite ion fluorescent probe, preparation method and application thereof |
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| DAOXUE LI等: "A mitochondria-targeted two-photon fluorescent probe for highly selective and rapid detection of hypochlorite and its bio-imaging in living cells", 《SENSORS AND ACTUATORS B》 * |
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| YANG YANG等: "A pyrene-based fluorescent and colorimetric chemodosimeter for the detection of ClO ions", 《ANAL. METHODS》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114249740A (en) * | 2021-11-23 | 2022-03-29 | 南京林业大学 | For detecting ClO-Ionic tanshinone benzimidazole type fluorescent probe and preparation method and application thereof |
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Application publication date: 20160608 |