CN113603725B - Bithiazole type metal iridium complex, preparation method and application thereof - Google Patents

Bithiazole type metal iridium complex, preparation method and application thereof Download PDF

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CN113603725B
CN113603725B CN202110738940.0A CN202110738940A CN113603725B CN 113603725 B CN113603725 B CN 113603725B CN 202110738940 A CN202110738940 A CN 202110738940A CN 113603725 B CN113603725 B CN 113603725B
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iridium
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尹建容
陶涛
刘芳妤
陈泽林
吕帅
余亭希
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Nanjing University of Information Science and Technology
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    • G01—MEASURING; TESTING
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    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract

The invention provides a dithiazole type metal iridium complex and a preparation method thereof, and provides application of the iridium complex in detection of solution viscosity, wherein the main structure of the iridium complex is bis (2-phenylpyridine) (4, 4 '-dibutyl-2, 2' -dithiazole) hexafluorophosphate without substituent groups, and R is one of hydrogen and bromine. The preparation method of the bithiazole metal iridium complex is simple, the compound presents weak fluorescence in a low-viscosity solvent, and presents strong fluorescence in a system with larger viscosity, so that the quick visual detection of the viscosity in a solution system can be realized, the compound can identify the viscosity with high selectivity, and a new development direction is provided for the synthesis of a novel viscosity probe.

Description

Bithiazole type metal iridium complex, preparation method and application thereof
Technical field:
the invention belongs to the technical field of metal iridium complexes, and particularly relates to a bithiazole type metal iridium complex, a preparation method and application thereof.
The background technology is as follows:
viscosity plays an important role in many diffusion-mediated biological processes, including interactions between biological macromolecules, pharmacokinetics, signal transduction, electron transport, and metabolite diffusion. Abnormal changes in intracellular viscosity are closely related to diseases and dysfunctions, such as higher viscosity of platelet membranes and erythrocytes in diabetics. The literature reports that the viscosity of normal cytoplasm is about 1-2cP, whereas the viscosity in diseased cells can be significantly increased, up to 140cP and even higher. Therefore, it is of great importance to perform qualitative and quantitative determination of intracellular viscosity.
The traditional methods for viscosity detection include a capillary viscometer, a falling ball viscometer and a rotary viscometer, and the mechanical methods are complex in operation, low in working efficiency and cannot be used for measuring the intracellular viscosity. In recent years, the fluorescent probe has been widely researched and applied because of the advantages of high sensitivity, good biocompatibility, capability of realizing real-time detection and the like, so that the development of a simple and sensitive fluorescent sensing material has great significance for qualitative and quantitative detection of the environment and even the viscosity in cells. Based on the above, the invention provides a bithiazole type iridium complex, a preparation method and application thereof to solve the problems.
The invention comprises the following steps:
the first object of the invention is to provide a metal iridium complex with a thiazole structure, which is specifically two structures, aiming at the defects of the prior art;
the second object of the invention is to provide a preparation method of a dithiazole type metal iridium complex;
the third object of the invention is to provide the application of the bithiazole metal iridium complex in viscosity detection.
The invention adopts the following technical scheme:
the bithiazole type metal iridium complex has a molecular structure shown as the following formula:
wherein the main structure is bis (2-phenylpyridine) (4, 4 '-dibutyl-2, 2' -bithiazole) iridium (III) hexafluorophosphate without substituent groups, and R is hydrogen or bromine.
Further, in the molecular structural formula of the bithiazole type metal iridium complex, R is hydrogen, and the iridium complex is bis (2-phenylpyridine) hexafluorophosphate (5, 5' -dihydro-4, 4' -dibutyl-2, 2' -bithiazole) iridium (III) and has a structure of a formula I-A.
Further, in the molecular structural formula of the bithiazole type metal iridium complex, R is bromine, and the iridium complex is bis (2-phenylpyridine) hexafluorophosphate (5, 5' -dibromo-4, 4' -dibutyl-2, 2' -bithiazole) iridium (III) and has a structure of a formula I-B.
The invention also provides a preparation method of the bithiazole metal iridium complex, which comprises the following steps:
s1, adding a chlorine bridge dimer [ Ir (ppy) into a reaction vessel under the protection of argon atmosphere 2 Cl] 2 5,5' -di R-4,4 '-dibutyl-2, 2' -dithiazole and dehydrated glycol react at a certain temperature, and after the reaction is finished, the mixture is cooled to room temperature;
wherein the chloro-bridged dimer [ Ir (ppy) 2 Cl] 2 Reference a;
reference B is made to the preparation of 5,5' -di-R-4, 4' -dibutyl-2, 2' -bithiazole.
Reference a: suin Jo, Y.S. chok. Yellow light-emitting electrochemical cells utilizing iridium (III) phenanthroimidazole complexes [ J ]. Molecular Crystals and Liquid Crystals,2017,654 (1): 221-233;
reference B: tao T, peng Y X, huang W, et al Coplanar Bithiazole-Centered Heterocyclic Aromatic Fluorescent Compounds Having Different Donor/Acceptor Terminal Groups [ J ]. Journal of Organic Chemistry,2013,78 (6): 2472-2481;
s2, dropwise adding NH into the S1 reaction system while stirring 4 PF 6 The water solution has yellow solid precipitated, is filtered after stirring, is washed by water, and takes out a filter cake;
s3, separating the filter cake obtained in the S2 by gel column chromatography to obtain pure solid, namely the bithiazole metal iridium complex
Further, in S1, a chlorine bridge dimer [ Ir (ppy) is added 2 Cl] 2 And 5,5' -di R-4,4' -dibutyl-2, 2' -bithiazole in an amount of 1 (2-4).
In S1, the reaction temperature is 140-190 ℃ and the reaction time is 16-24 hours.
Further, in S2, NH 4 PF 6 In aqueous solution, NH 4 PF 6 The concentration is 0.1mol/L, and the stirring time is 2-3 hours.
Further, in 5,5' -di R-4,4' -dibutyl-2, 2' -bithiazole, R is hydrogen or bromine.
The invention also provides application of the bithiazole type metal iridium complex in viscosity detection.
The invention has the beneficial effects that:
the invention provides two kinds of bithiazole type metal iridium complexes and a preparation method thereof, and provides application of the iridium complexes in the aspect of solution viscosity detection. The preparation method of the dithiazole type metal iridium complex is simple, the compound presents weak fluorescence in a low-viscosity solvent, and presents strong fluorescence in a system with larger viscosity, so that the quick visual detection of the viscosity in a solution system can be realized. In the ethanol-glycerol system, as the solution viscosity increases from 1.36cP to 669cP, the fluorescence probe intensity also gradually increases, and the fluorescence intensity has good linear relation with the environment viscosity, so that the fluorescence probe can be used for quantitatively detecting the environment viscosity. Moreover, the compound can identify the viscosity with high selectivity, and provides a new development direction for the synthesis of novel viscosity probes in the future.
Description of the drawings:
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of bis (2-phenylpyridine) (5, 5' -dihydro-4, 4' -dibutyl-2, 2' -bithiazole) iridium (III) hexafluorophosphate prepared in example 1 of the present invention;
FIG. 2 is a graph showing fluorescence emission spectra of bis (2-phenylpyridine) (5, 5' -dihydro-4, 4' -dibutyl-2, 2' -bithiazole) iridium (III) hexafluorophosphate prepared in example 1 of the present invention in ethanol-glycerol mixed solutions of different viscosities;
FIG. 3 shows the logarithmic value (Log I) of fluorescence intensity at a wavelength of 620nm of bis (2-phenylpyridine) (5, 5' -dihydro-4, 4' -dibutyl-2, 2' -bisthiazole) iridium (III) hexafluorophosphate produced in example 1 of the present invention 620 nm) and viscosity (Log eta);
FIG. 4 is a graph showing the selectivity of iridium (III) bis (2-phenylpyridine) (5, 5' -dihydro-4, 4' -dibutyl-2, 2' -bisthiazole) hexafluorophosphate produced in example 1 of the present invention.
The specific embodiment is as follows:
for the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
5,5' -dihydro-4, 4' -dibutyl-2, 2' -dithiazole (0.05 g,0.18 mmol) and chlorobridging dimer [ Ir (ppy) were weighed out 2 Cl] 2 (0.10 g,0.09 mmol) and ethylene glycol (8 mL) were added to a single neck round bottom flask, protected with an argon bulb, heated to 150℃and allowed to react for 16 hours, wherein the preparation of 5,5' -dihydro-4, 4' -dibutyl-2, 2' -dithiazole was described in reference B. After the completion of the reaction, the reaction mixture was cooled to room temperature, and NH was added dropwise to the reaction system at a concentration of 0.1mol/L while stirring 4 PF 6 The aqueous solution, which has yellow solid precipitated, is stirred for 2-3 hours, then is filtered, washed, the filter cake is taken out, gel column chromatography is used for purification, dichloromethane is used as a leaching agent, and the red solid is obtained with the yield of 94 percent. The nuclear magnetic spectrum is shown in figure 1, 1 H NMR(400MHz,CDCl 3 ):δ7.91(d,2H,pyridine),7.81(t,2H,pyridine),7.61(dd,4H,benzene),7.30(s,2H,thiazole),7.16(t,2H,pyridine),6.95(t,2H,benzene),6.79(t,2H,pyridine),6.08(d,2H,benzene)。
from the above data, it can be seen that bis (2-phenylpyridine) (5, 5' -dihydro-4, 4' -dibutyl-2, 2' -bithiazole) hexafluorophosphate iridium (III) has the structure of formula I-A:
example 2
5,5' -dibromo-4, 4' -dibutyl-2, 2' -bithiazole (0.05 g,0.10 mmol) was weighed out, and a chlorobridge dimer [ Ir (ppy) 2 Cl] 2 (0.05 g,0.05 mmol) ethylene glycol (10 mL) was added to a single neck round bottom flask, protected with an argon bulb, heated to 150℃and allowed to react for 16 hours, wherein the preparation of 5,5' -dibromo-4, 4' -dibutyl-2, 2' -bisthiazole was described in reference B. After the completion of the reaction, the reaction mixture was cooled to room temperature, and NH was added dropwise to the reaction system at a concentration of 0.1mol/L while stirring 4 PF 6 The water solution has yellow solid precipitated, and is stirred for 2-3 hours, filtered and waterWashing, taking a filter cake, purifying by using gel column chromatography, and taking dichloromethane as a leaching agent to obtain red solid with the yield of 77%. 1 H NMR(400MHz,CDCl 3 ):δ7.91(d,2H,pyridine),7.81(t,2H,pyridine),7.61(dd,4H,benzene),7.16(t,2H,pyridine),6.95(t,2H,benzene),6.79(t,2H,pyridine),6.08(d,2H,benzene)。
From the above data, bis (2-phenylpyridine) hexafluorophosphate (5, 5' -dibromo-4, 4' -dibutyl-2, 2' -bithiazole) iridium (III) has the structure of formula I-B:
test example 1
A solution of the compound obtained in example 1 in Dimethylformamide (DMF) was prepared at a concentration of 0.1mM and used as a mother liquor.
10 sample bottles containing 1.00mL of mother liquor were aligned, 9.00mL of solutions of different viscosities (volume ratios of absolute ethanol to glycerol 10:0, 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, 1:9) were pipetted into 10 bottles, respectively, shaken well, sonicated for 1 minute, compound final concentration 10. Mu.M, and fluorescence detection (lambda.) ex =400 nm), the fluorescence intensity in each system was scanned, as shown in fig. 2; log eta (eta is the viscosity value) is taken as the abscissa, log I 620 A standard curve of fluorescence intensity versus viscosity at 620nm was established on the ordinate, as shown in FIG. 3.
As can be seen from FIG. 2, the fluorescence intensity at 620nm gradually increases with increasing viscosity (in FIG. 2, the fluorescence intensity curves of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% of glycerol content are shown in order from bottom to top). As can be seen from fig. 3, there is a good linear relationship between fluorescence intensity and viscosity, and the linear equation is y=1.99+0.33 x; the compound is demonstrated to be capable of quantitative detection of viscosity changes for solutions having viscosity values in the range of 1.36-49.6 cP.
The iridium complex prepared in example 2 was subjected to a viscosity test in accordance with the method of example 1,
the results show that the iridium complex prepared in example 2 gradually increases in fluorescence intensity at 635nm with increasing viscosity, and the fluorescence intensity has a good linear relationship with viscosity, and the linear equation is y=2.13+0.31 x; the compound is demonstrated to be capable of quantitative detection of viscosity changes for solutions having viscosity values in the range of 1.36-49.6 cP.
Therefore, the two bithiazole metal iridium complexes provided by the invention can be used for quantitatively detecting the viscosity of the environment.
Test example 2
A DMF solution of the compound obtained in example 1 was prepared at a concentration of 0.1mM and used as a test mother liquor.
7 parts of 1mL of mother solution was prepared, and then 9mL of 1mM active molecule (Cu 2+ 、Na + 、HSO 3 - 、H 2 O 2 GSH, gly), and glycerol was added in another portion to give a final concentration of 10 μm, followed by fluorescence detection (λex=400 nm). The fluorescence intensity is plotted on the abscissa with wavelength and on the ordinate with the corresponding active molecule on the abscissa and on the ordinate with the fluorescence intensity at 620nm on the ordinate with 4b. As can be seen from FIG. 4, the probe acted on other active molecules, the fluorescence intensity was not substantially enhanced, but the fluorescence intensity was significantly enhanced in glycerol, indicating that the compound was able to specifically respond to viscosity.
According to the method of example 1, the iridium complex prepared in example 2 is tested for specific response viscosity, and the result shows that the iridium complex has no effect on other active molecules, but the fluorescence intensity in glycerol is obviously enhanced, so that the two dithiazole type metal iridium complexes provided by the invention can have specific response viscosity.
The foregoing is merely a preferred embodiment of the present invention, and the scope of the present invention is not limited to the above embodiments, but all technical solutions falling under the concept of the present invention fall within the scope of the present invention, and it should be noted that, for those skilled in the art, several modifications and adaptations without departing from the principles of the present invention should and are intended to be regarded as the scope of the present invention.

Claims (5)

1. The application of the bithiazole type iridium (III) complex in viscosity detection is characterized in that the bithiazole type iridium (III) complex has a molecular structure shown in the following formula:
；
wherein R is hydrogen or bromine.
2. The use of the bithiazole-type iridium (III) complex according to claim 1 in viscosity detection, wherein the preparation method of the bithiazole-type iridium (III) complex comprises the following steps:
s1, adding a chlorine bridge dimer [ Ir (ppy) into a reaction vessel under the protection of argon atmosphere 2 Cl] 2 Reacting 5,5' -di R-4,4' -dibutyl-2, 2' -dithiazole with dehydrated ethylene glycol at a certain temperature, and cooling to room temperature after the reaction is finished; in the 5,5' -di R-4,4' -dibutyl-2, 2' -bithiazole, R is hydrogen or bromine;
s2, dropwise adding NH into the S1 reaction system while stirring 4 PF 6 The water solution has yellow solid precipitated, is filtered after stirring, is washed by water, and takes out a filter cake;
s3, separating the filter cake obtained in the step S2 by gel column chromatography to obtain a pure solid, namely the bithiazole type metal iridium (III) complex.
3. Use of the bithiazole iridium (III) complex as claimed in claim 2 for viscosity measurement, wherein in S1, a chlorobridge dimer [ Ir (ppy) is added 2 Cl] 2 The mass ratio of the 5,5' -di R-4,4' -dibutyl-2, 2' -dithiazole is 1 (2-4).
4. The use of the bithiazole iridium (III) complex as claimed in claim 2 in viscosity detection, wherein in S1, the reaction temperature is 140-190 ℃ and the reaction time is 16-24 hours.
5. Use of the bithiazole iridium (III) complex as claimed in claim 2 for viscosity detection, wherein in S2, NH 4 PF 6 In aqueous solution, NH 4 PF 6 The concentration is 0.1mol/L, and the stirring time is 2-3 hours.
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