CN102584899A - Phosphorescent iridium complex, and preparation method and application thereof - Google Patents

Phosphorescent iridium complex, and preparation method and application thereof Download PDF

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CN102584899A
CN102584899A CN2011104594626A CN201110459462A CN102584899A CN 102584899 A CN102584899 A CN 102584899A CN 2011104594626 A CN2011104594626 A CN 2011104594626A CN 201110459462 A CN201110459462 A CN 201110459462A CN 102584899 A CN102584899 A CN 102584899A
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iridium complex
phosphorescent iridium
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pba
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毛兰群
杨丽芬
姜琴
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Institute of Chemistry CAS
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Abstract

The invention discloses a phosphorescent iridium complex, and a preparation method and application thereof. A chemical formula of the phosphorescent iridium complex is [Ir(pba)2(DMSO)2]PF6 and a structural formula of the phosphorescent iridium complex is shown as a formula (I), wherein pba is expressed as 4-(2-pyridyl)benzaldehyde, DMSO is expressed as dimethylsulfoxide. A method for preparing the phosphorescent iridium complex comprises the following steps of: reacting a complex shown as a formula (II) with the dimethylsulfoxide; and adding potassium hexafluorophosphate into a reaction system and stirring to obtain the phosphorescent iridium complex. The invention also provides application of the phosphorescent iridium complex to the detection of glutamine. By the phosphorescent iridium complex, the high-selectivity and high-sensitivity detection of the glutamine can be realized, and a possibility for constructing a fluorescent chemical sensor for detecting the glutamine in high selectivity and high sensitivity is provided; and the phosphorescent iridium complex has a high dyeing effect on the glutamine in cells, and is expected to be used for detecting the Gln in the physiological and pathological processes.

Description

A kind of phosphorescent iridium complex and preparation method thereof and application
Technical field
The present invention relates to a kind of phosphorescent iridium complex and preparation method thereof and application.
Background technology
Stimulina (Glutamine, be called for short Gln) is one of rich in amino acid of Mammals in-vivo content, and concentration is 0.6～0.9mmol/L among the human normal plasma, accounts for 20% of blood plasma total free amino acid, accounts for 60% of total free amino acid in the body.Nineteen thirty-five, Kerbs finds the ability that the Mammals kidney is synthetic and decompose Gln first, stresses that " most amino acid all have multiple function, but the function of Gln is the abundantest." Eagle (and H.Eagle.J.Biol.Chem.1955,214,839-852), Windmueller (H.G. Windmueller.Advanced in Enzymology and Related Areas of Molecular Biology.1982,53; 210-237), Kapadia (C.R.Kapadia, M.F.Colpoys, Z.M.Jiang; D.J.Johnson, R.J.Smith, D.W. Wilmore.J.Parenter. Enter. Nutr.1985; 9,583-589), Alverdy (J.C.Alverdy.J.Parenter. Enter.Nutr. 1990,14; S109-S113), Souba (W. W. Souba.Ann. Surg.1993,218,715-728; 217; 655-667) point out that respectively the mammalian cell of cultivating needs Gln; And emphasical Gln is a kind of important nutrient substance, is the precursor substance of synthesizing amino acid, protein, nucleic acid and many other biological molecules, not only in liver, kidney, small intestine and muscle metabolism, plays important regulating effect; And be the main carrier that each organ is transported amino acid and nitrogen in the body, be the main fuel of the rapid cell of growth.Gln has caused people's common concern as a kind of special nutritive substance, and becomes research focus in recent years.1998, people such as Pittner were developed a kind of flow injection method based on glutamine content in the enzyme linked immunological indirect detection cell culture medium; 1998, Hernandez etc. reported a kind of and have detected the glutamine content in the first stream patient cerebrospinal fluid based on capillary zone electrophoresis-laser induced fluorescence(LIF) method, but these methods all exist shortcomings such as complex operation, instrument cost an arm and a leg, detectability height.
Phosphorescent metal title complex (Re I, Ru II, Os II, Rh III, Ir III) wait and generally have unique d 6, d 8, d 10The spin coupling can take place in electronic structure between the heavy metal atom, singlet state and triplet state are mixed; The symmetry of triplet exciton is destroyed, and decay accelerates, and metal-ligand charge transfer (MLCT) takes place; Make singlet state also have some triplet state character simultaneously; Fall time is elongated, has improved (ISC) efficient that jumps that from the singlet state to the triplet state, leaps up between system, thereby has sent high efficiency phosphorescent.Compare with organic fluorescent dye, the phosphorescence heavy metal complex has bigger Stokes displacement and long emission lifetime, and its long emission lifetime helps the duration of service resolution techniques makes phosphorescent signal distinguish mutually with the fluorescent signal of background.
In common a few heavy metal species title complexs, Ir IIITherefore title complex, is necessary Ir because phosphorescent lifetime is relatively short, the luminescent quantum productive rate is high, glow color receives much concern in fields such as electroluminescent, fluorescent probe, bio-imagings in advantages such as whole visibility region are adjustable IIITitle complex is further studied.
Summary of the invention
The purpose of this invention is to provide a kind of phosphorescent iridium complex and preparation method thereof and application.
A kind of phosphorescent iridium complex provided by the invention, its chemical formula is: [Ir (pba) 2(DMSO) 2] PF 6, wherein pba representes 4-(2-pyridyl) phenyl aldehyde, DMSO representes methyl-sulphoxide;
The structural formula of said phosphorescent iridium complex is suc as formula shown in (I),
Figure BDA0000128059900000021
The present invention also provides the preparation method of above-mentioned phosphorescent iridium complex, comprises the steps:
(chemical formula is [(pba) to structural formula suc as formula title complex shown in (II) 2Ir (μ-Cl 2) Ir (pba) 2], pba representes 4-(2-pyridyl) phenyl aldehyde) react with methyl-sulphoxide;
In said reacted reaction system, add Potassium Hexafluorophosphate and promptly get product through stirring;
Figure BDA0000128059900000022
Among the above-mentioned preparation method, title complex shown in the formula (II) can be 1 with the molfraction ratio of methyl-sulphoxide: (3～5), and as 1: 5.
Among the above-mentioned preparation method, the temperature of said reaction can be 110 ℃～150 ℃, as 120 ℃; The time of said reaction can be 2 hours～and 4 hours, as 2 hours.
Among the above-mentioned preparation method, title complex shown in the formula (II) can be 1 with the molfraction ratio of Potassium Hexafluorophosphate: (4～6), and as 1: 4.
Among the above-mentioned preparation method; Title complex shown in the formula (II) can prepare according to the method that comprises the steps: three hydration iridous chlorides and 4-(2-pyridyl) phenyl aldehyde reacts promptly in the mixing solutions of ethylene glycol ethyl ether and water and gets; The volume parts ratio of ethylene glycol ethyl ether and water can be 3: 1, specifically can under refluxad react 24 hours.
The present invention also provides the application of above-mentioned phosphorescent iridium complex in detecting Stimulina; In the said application, can in methyl-sulphoxide and phosphate buffer soln, detect Stimulina, the pH value of said phosphate buffer soln can be 7.0, and concentration is 50mM.
Phosphorescent iridium complex provided by the invention issues orange light at the 365nm ultra violet lamp, and maximum emission wavelength is positioned at about 557nm; Under the normal temperature condition, this complex of iridium and after Stimulina effect for some time (Stimulina can with Ir IIICoordination forms a five-membered ring structure, and can with part on-CHO forms hydrogen bond, realizes that the energy between metal and the part shifts), can send brighter blue light, its maximum emission peak is positioned at 475nm, its emissive porwer is [Ir (pba) 2(DMSO) 2] PF 6Title complex has improved nearly 100 times; Under the same terms; After other amino acid and the polypeptide (as: l-arginine, Histidine, L-glutamic acid, halfcystine, aspartic acid, glycocoll, tyrosine, L-Ala, Isoleucine, Methionin, l-asparagine, gsh, L-proglu-dipeptide) that contains glutamine residue and this complex of iridium effect; Its emissive porwer does not have obvious variation; Thereby complex of iridium provided by the invention can realize highly selective, the high-sensitivity detection of Stimulina, for the fluorescence chemical sensor that makes up a kind of highly selective, high-sensitivity detection Stimulina provides maybe; And the Stimulina in the phosphorescent iridium complex pair cell provided by the invention has stronger dyeing function, is expected to be used for the detection of the Gln of physiology, pathologic process.
Description of drawings
Fig. 1 is the image under the 365nm ultra violet lamp after complex of iridium provided by the invention and the different aminoacids effect; Wherein, Fig. 1 (a) be after complex of iridium provided by the invention and the different aminoacids effect in 365nm ultra violet lamp figure, Fig. 1 (b) for complex of iridium of the present invention and Stimulina effect front and back in 365nm ultra violet lamp figure.
Fig. 2 is the emmission spectrum figure after complex of iridium provided by the invention and the different aminoacids effect.
Fig. 3 is the cyclic voltammogram after complex of iridium provided by the invention and the Stimulina effect.
Fig. 4 is the laser co-focusing imaging after complex of iridium provided by the invention and the Stimulina effect, and wherein, Fig. 4 (a) is the laser co-focusing imaging of Hela cell, and Fig. 4 (b) is that the Hela cell is through [Ir (pba) 2(DMSO) 2] PF 6Laser co-focusing imaging after title complex is hatched, Fig. 4 (c) is that the Hela cell is through [Ir (pba) 2(DMSO) 2] PF 6Laser co-focusing imaging after the mixing solutions of title complex and Stimulina is hatched.
Embodiment
Employed experimental technique is ordinary method like no specified otherwise among the following embodiment.
Used material, reagent etc. like no specified otherwise, all can obtain from commercial sources among the following embodiment.
The preparation and the application thereof of phosphorescent iridium complex shown in the formula (I)
1, title complex shown in the formula (II) [(pba) 2Ir (μ-Cl 2) Ir (pba) 2] preparation
Reference literature (W. Tan, Q.Zhang, J.J.Zhang, H.Tian.Org.Lett.2009,11,161-164).
Take by weighing the IrCl of 1mmol 3H 2O and 2.5mmol 4-(2-pyridyl) phenyl aldehyde is dissolved in the mixing solutions of ethylene glycol ethyl ether and water (volume ratio 3: 1), heating, stirring and refluxing 24h, yellow mercury oxide; Suction filtration is drying to obtain [(pba) 2Ir (μ-Cl 2) Ir (pba) 2].
1H?NMR(300MHz?CDCl 3)δppm：9.52(s，4H；CHO)，9.27(dd，4H)，8.06(d，4H)，7.94(dt，4H)，7.68(d，4H)，7.31(dd，4H)，6.98(dt，4H)，6.37(d，4H)。MALDI-TOF mass spectrum m/z [M +]: 556.62{ [Ir (pba) 2] +
2, [the Ir (pba) of phosphorescent iridium complex shown in the formula (I) 2(DMSO) 2] PF 6Preparation
Take by weighing 0.085g (0.079mmol) [(pba) 2Ir (μ-Cl 2) Ir (pba) 2] and 30mL DMSO reaction, wherein, [(pba) 2Ir (μ-Cl 2) Ir (pba) 2] with the mol ratio of DMSO be 1: 5, be heated to 120 ℃ and keep reaction 2h, yellow solution, be cooled to room temperature, add Potassium Hexafluorophosphate again, the Potassium Hexafluorophosphate of adding with [(pba) 2Ir (μ-Cl 2) Ir (pba) 2] mol ratio be 4: 1, stir 1h, suction filtration, underpressure distillation then; Solid is an eluent with methylene dichloride and acetone (volume ratio 15: 1), separates with silicagel column, promptly gets [the Ir (pba) of orange red solid shown in the formula (I) 2(DMSO) 2] PF 6, productive rate: 65.8%.
1HNMR(300MHz，DMSO-d 6，TMS)δppm：9.88(s，2H；CHO)，9.58(s，2H)，8.49(d，2H)，8.25(t，2H)，8.00-8.07(m，4H)，7.74(t，1H)，7.64(t，1H)，7.47(m，1H)，7.43(m，2H)，6.75(s，1H)，2.51(s，4H)。MALDI-TOF mass spectrum m/z [M +]: 556.62{ [Ir (pba) 2] +Ultimate analysis: calculated value (is pressed C 28H 28IrN 2S 2O 4H 2OCH 2Cl 2Calculate): C:42.66; N:3.44; H:3.92; Measured value: C:42.99; N:3.29; H:3.89.
3, [the Ir (pba) of phosphorescent iridium complex shown in the formula (I) 2(DMSO) 2] PF 6Interaction with the different aminoacids molecule
[Ir (pba) with preparation 2(DMSO) 2] PF 6Pressed powder is dissolved in the DMSO solution; And with DMSO/ (phosphate buffer soln, PBS (pH 7.0,50mM)) (volume ratio 1: 49) dilution; Final preparation concentration is the Ir complex solution of 10 μ M; Add equal-volume, isocyatic different aminoacids (final concentration is 500 μ M) again, normal-temperature reaction two days is carried out the mensuration of photophysical property then respectively to it.
Test result is as illustrated in fig. 1 and 2, with [Ir (pba) 2(DMSO) 2] PF 6Complex solution is compared, and after adding Stimulina, solution demonstrates stronger blue light; Emission wavelength is blue shifted to 475nm by 557nm; Fluorescence intensity increases nearly 100 times, and phosphorescent lifetime also is reduced to 7ns by 100ns, and this is because behind the Stimulina replacement DMSO; This title complex triplet excitation changes singlet state into and excites, and the time that the excited state electronics returns ground state shortens greatly; Under the same terms, other amino acid and the polypeptide (as: l-arginine, Histidine, L-glutamic acid, halfcystine, aspartic acid, glycocoll, tyrosine, L-Ala, Isoleucine, Methionin, l-asparagine, gsh and L-proglu-dipeptide) and [Ir (pba) that contain glutamine residue 2(DMSO) 2] PF 6After the title complex effect, its emissive porwer does not have obvious variation, thereby complex of iridium probe provided by the invention can be realized the highly selective and the high-sensitivity detection of Stimulina; Can know that by above-mentioned experiment complex of iridium provided by the invention can reach 500nmol/L to the minimum limit of determination of Stimulina.
4, [the Ir (pba) of phosphorescent iridium complex shown in the formula (I) 2(DMSO) 2] PF 6Electro-chemical test
Adopt three-electrode system, glass-carbon electrode is a working electrode, and platinum electrode is a supporting electrode; Ag/AgCl (saturated KCl) electrode is a reference electrode; Solvent: anhydrous acetonitrile, supporting electrolyte: the phosphofluoric acid 4-butyl amine, adopt cyclic voltammetry to go up at electrochemical workstation (CHI 660B) and accomplish.
Test result is as shown in Figure 3, as can be seen from the figure [Ir (pba) 2(DMSO) 2] PF 6Good redox reversible peak appears in title complex near+1.22V (vsAg/AgCl, saturated KCl), and redox peak-to-peak current potential difference DELTA E=67mV, approaches theoretical value 59mV basically.After adding Stimulina; The oxidation peak summit current has obvious increase; And the reduction peak summit current almost remains unchanged, and this also interacts from existing between another angle this complex of iridium of explanation and the Stimulina, and summit current to change inconsistent possible cause be oxidation state Ir IVWith go back ortho states Ir IIIDifferent with the Stimulina coordination ability, the spread coefficient of oxidation state complex of iridium from the solution bulk diffusion to electrode surface accelerates, thereby it is inconsistent to cause the redox peak to peak current to change.
5, [the Ir (pba) of phosphorescent iridium complex shown in the formula (I) 2(DMSO) 2] PF 6Cell toxicity test
The cell that the present invention tests employing is Hela cell (cervical cancer cell), purchases in BJ Union Hospital.
[the Ir (pba) of preparation different concns (10,20,40,60,80,100 μ M) 2(DMSO) 2] PF 6Complex solution treats that cell after 5～6 hours, cleans twice with PBS solution in adherent growth in 96 orifice plates, respectively adds [the Ir (pba) of 100 μ L different concns again 2(DMSO) 2] PF 6Solution is hatched 2h, cleans twice with PBS solution again, adds the CCK-8 staining reagent at last, on ELIASA, surveys absorbancy after 2 hours and changes.
Experimental result shows that the Hela cell is the [Ir (pba) of 10 μ M and 20 μ M in concentration 2(DMSO) 2] PF 6After hatching 2h in the complex solution, cell viability still can reach more than 95% and 90%, explains that complex of iridium provided by the invention has hypotoxicity.
6, [the Ir (pba) of phosphorescent iridium complex shown in the formula (I) 2(DMSO) 2] PF 6Laser co-focusing imaging
With [Ir (pba) 2(DMSO) 2] PF 6Title complex is dissolved in DMSO/PBS (volume ratio 1: 49), and (pH 7.0; 50mM); After this complex solution that in PBS, adds final concentration and be 10 μ M is hatched Hela cell 2h; Clean twice with PBS solution, under Olympus FV1000 laser scanning co-focusing microscope, excite then, gather the emission light in 440～480nm scope in 405nm.
The result is as shown in Figure 4, the cell autofluorescence a little less than, when adding [Ir (pba) 2(DMSO) 2] PF 6After solution is hatched for some time, the luminous grow of tenuigenin part; And add [Ir (pba) 2(DMSO) 2] PF 6After hatching for some time with the mixing solutions of Gln; Tenuigenin part fluorescence becomes brighter; Explain that complex of iridium provided by the invention can get into cell through cytolemma; Stimulina in the pair cell has stronger dyeing function, and the variation of Stimulina in bio-imaging and studying physiological, the pathologic process is had great importance.

Claims (8)

1. phosphorescent iridium complex, its chemical formula is: [Ir (pba) 2(DMSO) 2] PF 6, wherein pba representes 4-(2-pyridyl) phenyl aldehyde, DMSO representes methyl-sulphoxide;
The structural formula of said phosphorescent iridium complex is suc as formula shown in (I),
Figure FDA0000128059890000011
2. the preparation method of the said phosphorescent iridium complex of claim 1 comprises the steps:
Structural formula reacts suc as formula title complex shown in (II) and methyl-sulphoxide;
In said reacted reaction system, add Potassium Hexafluorophosphate and promptly get product through stirring;
Figure FDA0000128059890000012
3. method according to claim 2 is characterized in that: title complex shown in the formula (II) is 1 with the molfraction ratio of methyl-sulphoxide: (3～5).
4. according to claim 2 or 3 described methods, it is characterized in that: the temperature of said reaction is 110 ℃～150 ℃; The time of said reaction is 2 hours～4 hours.
5. according to arbitrary described method among the claim 2-4, it is characterized in that: title complex shown in the formula (II) is 1 with the molfraction ratio of Potassium Hexafluorophosphate: (4～6).
6. according to arbitrary described method among the claim 2-5, it is characterized in that: title complex shown in the formula (II) is to prepare according to the method that comprises the steps: three hydration iridous chlorides and 4-(2-pyridyl) phenyl aldehyde reacts promptly in the mixing solutions of ethylene glycol ethyl ether and water and gets.
7. the application of the said phosphorescent iridium complex of claim 1 in detecting Stimulina.
8. application according to claim 7 is characterized in that: in methyl-sulphoxide and phosphate buffer soln, Stimulina is detected, the pH value of said phosphate buffer soln is 7.0, and concentration is 50mM.
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