CN103555321A - Phosphorescent ionic type iridium complex probe and preparation method and application thereof - Google Patents
Phosphorescent ionic type iridium complex probe and preparation method and application thereof Download PDFInfo
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- CN103555321A CN103555321A CN201310525077.6A CN201310525077A CN103555321A CN 103555321 A CN103555321 A CN 103555321A CN 201310525077 A CN201310525077 A CN 201310525077A CN 103555321 A CN103555321 A CN 103555321A
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Abstract
The invention discloses a phosphorescent ionic type iridium complex probe and a preparation method and application thereof, and particularly relates to a phosphorescent iridium complex for detecting hypochlorite (ClO<->) and containing an oxime group (C=N-OH) and an application thereof. The material of the complex consists of a ring metal ligand containing an oxime group, a metal center and an N^N ligand, and the structural general formula is shown in the specification. The synthesis steps of the material are simple, the conditions are mild, and the material has very good application prospects in hypochlorite detection, cell imaging and bio-labeling.
Description
Technical field
The invention belongs to organic photoelectric functional material technical field.Be specifically related to preparation method and the application in hypochlorite detection, cell imaging and biomarker thereof of a class phosphorescent iridium complex material.
Background technology
Molecular oxygen is the essential component that all oxygen consumption organisms maintain its vital movement, active oxygen species (ROS) is a kind of of the molecular oxygen that produces in body metabolism process, and it comprises oxygen and the hypochlorous acid/hypochlorite of superoxide, hydroxyl, peroxy radical, hydrogen peroxide, singlet.Active oxygen species ROS in human body is mainly the oxygen producing by mitochondrial respiratory process, meanwhile, also can be induced in organism and be generated by external disturbance, for example xenobiotics, infectious agent and ultraviolet ray.ROS participates in physiology and pathologic process widely, as signal transduction, and inflammation, canceration and the damage of nervous tissue decline property.Although producing ROS in normal cellular environment is necessary for life, when they generate when excessive under external source sexual stimulus, organism is also had to harm.The oxidative stress that the oxidation of excessive ROS by biomolecules causes, for example, the oxygenizement of lipid, protein and DNA, and inducing cell death.
ROS regulates various physiological processs.Hypochlorous acid (HOCl), the active oxygen of a biological significance, is in activated leukocyte cell, by myeloperoxidase (MPer) catalysis chlorine peroxide ion, produces.In naturally defending, hypochlorous acid is also a kind of important sterilant.Yet the abnormal disease relevant to many inflammation of hypochlorous acid level has close contacting, and comprises cardiovascular disorder, the damage of human erythrocyte, tuberculosis, rheumatoid arthritis and cancer.So hypochlorous detection is very important.At present, developed the hypochlorous method of many detections, for example, electrolytic process, potential method, spectrophotometry, chemiluminescence detection etc.WeiyingLin has been combined into a kind of detection ClO
-ratio fluorescent probe, when acting on analyte, fluorescent emission ratio (I
509/ I
439) can be increased to 2.74 from 0.28, and there is higher selectivity (Chem.Eur.J., 2009,15,2305 – 2309).This probe is the detection based on fluorescent signal.Than fluorescent signal, phosphorescent signal detects has following advantage: have large Stokes displacement, excited by visible light, good light stability, long emission lifetime, high quantum yield and emission wavelength and easily regulate etc.Wherein large Stokes shift can be easy to distinguish and excites and launch, and long emission lifetime serviceable time resolution techniques is distinguished improve signal to noise ratio and the sensitivity of detection and can use visible ray to excite reduction photobleaching with background fluorescence signal mutually.Therefore it is significant that, exploitation has optionally, can be used for the phosphorescence probe of living body detection.
Summary of the invention
Technical problem: the object of the present invention is to provide the complex of iridium of a class phosphorescent emissions, provide their preparation method, and propose this application of class title complex in hypochlorite detection, cell imaging and biomarker.
Technical scheme: the present invention closes and relates to a kind of phosphorescence ionic type iridium complex, is characterized in that containing oximido group (C=N-OH) on its cyclic metal complexes, can be used to selectivity and detects hypochlorite;
The ionic type iridium complex of described phosphorescent emissions is characterized in that this complex of iridium has following general structure:
Wherein, N^N part can be lower array structure,
The preparation method of the complex of iridium of described phosphorescent emissions, is characterized in that synthetic route is as follows:
Step I. under nitrogen protection, 2-phenyl aldehyde yl pyridines and three hydration iridous chlorides 110 ℃ of confined reactions in cellosolvo/water (3:1, v:v) mixed solution obtain iridium dichloro bridge for 24 hours;
Step I i. by the dichloro bridge obtaining and N^N part at methylene chloride/methanol (2:1, v:v) lower 40 ℃ of confined reactions of nitrogen protection 4 hours in mixed solution, after being cooled to room temperature, add Potassium Hexafluorophosphate to continue reaction 1 hour, separating-purifying obtains the complex of iridium that contains aldehyde radical (CHO);
Step I ii. by the complex of iridium that contains aldehyde radical again with oxammonium hydrochloride 60 ℃ of confined reactions 3 hours under nitrogen protection in ethanol/triethylamine mixed solution, separating-purifying obtains the final title complex that contains oximido group (C=N-OH).
Described phosphorescent emissions ionic type iridium complex can be applicable to hypochlorite and detects.
Described phosphorescent emissions ionic type iridium complex can be applicable to cell imaging and biomarker.
Beneficial effect: the synthetic material of the present invention is used as ClO
-phosphorescence probe, at ClO
-existing lower phosphorescent emissions significantly to strengthen, is turn-on type phosphorescence probe, detects effect remarkable.Phosphorescence probe material prepared by the present invention is to ClO
-there is high selectivity, and response is fast.
This probe material has low bio-toxicity, and easily enters in cell cytosol, makes this class probe can be used for ClO in cell
-detect, this is to further investigation ClO
-physiology and toxicological effect in organism body are significant.
Accompanying drawing explanation
Fig. 1. be the CH of phosphorescence probe Ir-2 in embodiment 3
3oH/H
2the uv-visible absorption spectra of O mixing solutions is to ClO
-responsiveness;
Fig. 2. be the CH of phosphorescence probe Ir-2 in embodiment 4
3oH/H
2the phosphorescent emissions spectrum of O mixing solutions is to ClO
-responsiveness;
Fig. 3. for phosphorescence probe Ir-2 in embodiment 5 is to ClO
-selectivity schematic diagram;
Fig. 4. for phosphorescence probe Ir-2 in embodiment 6 is for detection of ClO in cell
-laser Scanning Confocal Microscope photo.
Embodiment
In order to understand better the content of patent of the present invention, below by concrete example, further illustrate technical scheme of the present invention.But these embodiments do not limit the present invention.
Embodiment 1: when N^N part is
when (diquinolyl), contain the preparation of the complex of iridium Ir-1 of aldehyde radical (CHO):
Title complex Ir-1: take 4-(2-pyridyl) phenyl aldehyde (2.5mmol) and IrCl
33H
2o(1mmol) mix and drop in three-necked bottle, vacuumize on biexhaust pipe-Bao nitrogen-vacuumize, moves in circles three times, finally adopts the whole reaction system of nitrogen protection.The ethylene glycol ethyl ether that is 3:1 by volume ratio and the mixture of water are injected in reaction system, are warming up to 110 ℃, magnetic agitation reaction 24 hours.After reaction finishes, system is cooled to room temperature, filtering-depositing, and with ethanol and washing, the solid product obtaining is pyridyl phenyl aldehyde iridium dichloro bridge, can directly drop into next step reaction.
Take C^N cyclic metal complexes dichloro bridge (1mmol), diquinolyl (2.3mmol) is added in three-necked bottle, vacuumize on biexhaust pipe-Bao nitrogen-vacuumize, moves in circles three times, finally adopts the whole reaction system of nitrogen protection.In the mixture injection system of the methylene dichloride that is 2:1 by volume ratio and methyl alcohol, temperature is risen to 50 ℃, stirring and refluxing.React after 5 hours, add the Potassium Hexafluorophosphate solid of 0.72mmol, continue stirring reaction and spend the night.Reaction finishes rear concentrated purification, finally uses methylene dichloride and normal hexane recrystallization, obtains solid product and is complex of iridium Ir-1.Productive rate: 94%.
1H?NMR(400MHz,DMSO):δ=9.68(s,1H),9.01(d,J=8.9Hz,1H),8.94(d,J=8.7Hz,1H),8.37(d,J=8.0Hz,1H),8.11(d,J=7.9Hz,1H),8.07(d,J=8.1Hz,1H),8.02(t,J=6.4Hz,2H),7.68(d,J=8.9Hz,1H),7.57(t,J=7.5Hz,1H),7.50(d,J=8.0Hz,1H),7.23(t,J=6.6Hz,1H),7.16(t,J=7.9Hz,1H),6.64(s,1H)。
Embodiment 2: the preparation of the title complex Ir-2 that contains oximido group (C=N-OH):
The preparation of title complex Ir-2: take complex of iridium Ir-1(1mmol) and oxammonium hydrochloride (5mmol) add in two-neck bottle, vacuumize on biexhaust pipe-Bao nitrogen-vacuumize, moves in circles three times, finally adopts the whole reaction system of nitrogen protection.Inject the ethanolic soln that 5mL steamed, the triethylamine that 5mmol steamed, 60 ℃ of mix and blends 4 hours.After reaction finishes, concentrated purification.Obtain red solid product and be complex of iridium Ir-2.Productive rate: 81%.
1h NMR (400MHz, DMSO): δ=11.14 (s, 1H), 10.53 (s, 9H), 10.36 (s, 2H), 9.03 – 9.00 (m, 1H), 8.94 – 8.91 (m, 1H), 8.18 (s, 1H), 8.10 (s, 1H), 7.88 (d, J=10.4Hz, 2H), 7.85 (s, 1H), 7.83 (d, J=4.0Hz, 2H), 7.82 (s, 1H), 7.57 (t, J=7.4Hz, 2H), 7.15 (t, J=9.0Hz, 3H), 7.08 (t, J=6.5Hz, 2H), 6.47 (s, 1H);
13cNMR (101MHz, DMSO) δ=166.19,160.22,150.95,148.76,148.72,148.58,147.72,144.89,144.40,141.89,139.35,134.31,131.39,130.01,129.34,127.65,127.60,125.71,124.41,122.69,122.42,120.77; [m/e] (M, MALDI-TOF) theoretical value: 842.94, experimental value: 843.107.
Embodiment 3: the uv-visible absorption spectra of probe I r-2 is to ClO
-responsiveness:
Complex of iridium Ir-2 is dissolved in to CH
3oH/H
2o(v/v, 2:1, pH7.2) in mixing solutions, successively add ClO
-cH
3oH/H
2in O mixing solutions, drip ClO at every turn
-after, in 37 ℃ of waters bath with thermostatic control, heated and stirred is 5 minutes, makes ClO
-ir-2 fully reacts with complex of iridium, tests subsequently its uv-absorbing intensity.As shown in Figure 1, along with ClO
-add, having there is variation in the absorption spectrum of complex of iridium Ir-2 solution, is accompanied by ClO at once
-drip the rising of concentration, work as ClO
-dropping concentration equivalent while reaching 30eq., titration reaches terminal, then continues to drip ClO
-, spectrum no longer changes.
Embodiment 4: the emmission spectrum of probe I r-2 is to ClO
-responsiveness::
Complex of iridium Ir-2 is dissolved in to CH
3oH/H
2o(v/v, 2:1, pH7.2) in mixing solutions, successively add ClO
-cH
3oH/H
2in O mixing solutions, drip ClO at every turn
-after, in 37 ℃ of waters bath with thermostatic control, heated and stirred is 5 minutes, makes ClO
-ir-2 fully reacts with complex of iridium, tests subsequently its fluorescence emission spectrum, as shown in Figure 2.At 608nm place, complex of iridium Ir-2 solution itself is luminous very weak, along with ClO
-add, having there is variation in the fluorescence spectrum of complex of iridium Ir-2 solution, is accompanied by ClO at once
-drip the rising of concentration, fluorescence spectrum blue shift the fluorescence intensity at 597nm place of complex of iridium Ir-2 raise gradually.Work as ClO
-dropping concentration equivalent while reaching 30eq., titration reaches terminal, then continues to drip ClO
-, spectrum no longer changes.
Embodiment 5: probe I r-2 in solution to ClO
-selectivity experiment:
Prepare the complex solution (CH of 10 μ M
3oH/H
2o(v/v, 2:1, pH7.2)), pipette compound solution that 2.5mL joins in cuvette, add the AlCl of excessive (surpassing 200 times of equivalents)
3, CuCl
2, LiClO
3, MgCl
2, Na
2cO
3, Na
2sO
4, NaOAc, ZnCl
2, H
2o
2, NaClO
3, NaNO
2, NaClO solution, survey respectively its emmission spectrum.As shown in Figure 3, other ions all have no significant effect test result.Experimental data shows: material is to ClO
-there is good selectivity.
Embodiment 6: viable cell imaging experiment:
Hela cell is cultivated according to American Type Tissue Culture Collection regulation.Hela cell is hatched 30 minutes with 20 μ M complex of iridium Ir-2 solution at 37 ℃, with nutrient solution washing 3 times, as the Laser Scanning Confocal Microscope photo result of blank group as shown in Figure 4, substantially there is no fluorescent emission in viable cell; Experimental group is hatched after 30 minutes with 20 μ M complex of iridium Ir-2 at Hela cell under 37 ℃ of conditions, with 200 μ MNaClO solution, under 37 ℃ of conditions, hatch 30 minutes again, afterwards with substratum washing 3 times, be placed under Laser Scanning Confocal Microscope and take pictures, photo shows in viable cell endochylema stronger phosphorescent emissions, and result as shown in Figure 4.This experimental result shows, complex of iridium Ir-2 can be used for detecting the ClO in viable cell
-.
Claims (4)
1. a phosphorescence ionic type iridium complex probe, is characterized in that on its cyclic metal complexes, containing oximido rolls into a ball C=N-OH; This complex of iridium has following general structure:
Wherein, N^N part is lower array structure,
2. a preparation method for phosphorescence ionic type iridium complex probe as claimed in claim 1, is characterized in that this preparation method's synthetic route is as follows:
Step I. under nitrogen protection, 2-phenyl aldehyde yl pyridines and three hydration iridous chlorides 110 ℃ of confined reactions in cellosolvo/water (3:1, v:v) mixed solution obtain iridium dichloro bridge for 24 hours;
Step I i. by the dichloro bridge obtaining and N^N part at methylene chloride/methanol (2:1, v:v) lower 40 ℃ of confined reactions of nitrogen protection 4 hours in mixed solution, after being cooled to room temperature, add Potassium Hexafluorophosphate to continue reaction 1 hour, separating-purifying obtains the complex of iridium that contains aldehyde radical (CHO);
Step I ii. by the complex of iridium that contains aldehyde radical again with oxammonium hydrochloride 60 ℃ of confined reactions 3 hours under nitrogen protection in ethanol/triethylamine mixed solution, separating-purifying obtains the final title complex that contains oximido group (C=N-OH).
3. a phosphorescence ionic type iridium complex probe as claimed in claim 1, is characterized in that this phosphorescence ionic type iridium complex is applied to hypochlorite and detects.
4. a phosphorescence ionic type iridium complex probe as claimed in claim 1, is characterized in that this phosphorescence ionic type iridium complex is applied to cell imaging and biomarker.
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Cited By (12)
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| CN103937487A (en) * | 2014-03-25 | 2014-07-23 | 南京邮电大学 | Phosphorescent fluorinion probe, preparation and applications thereof |
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| CN104086598A (en) * | 2014-06-17 | 2014-10-08 | 南京邮电大学 | Ionic iridium complex with bidentate ligand, and preparation method and application thereof |
| CN104610371A (en) * | 2015-01-27 | 2015-05-13 | 福州大学 | Iridium complex and application thereof |
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| CN110078772A (en) * | 2019-06-20 | 2019-08-02 | 福州大学 | Fluorescence probe based on complex of iridium and preparation method thereof and the application in hypochlorous acid detects |
| CN110243898A (en) * | 2019-07-13 | 2019-09-17 | 青岛科技大学 | A kind of preparation method based on annular metal iridium complex optical electro-chemistry molecular probe pH sensor |
| WO2019218594A1 (en) * | 2018-05-17 | 2019-11-21 | 南京邮电大学 | Water-soluble phosphorescent nanoparticle for detecting hypochlorous acid using ratio method and preparation method and application thereof |
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