CN110776547B - Platinum (II) complex/sodium deoxycholate hybrid material and preparation and application thereof - Google Patents
Platinum (II) complex/sodium deoxycholate hybrid material and preparation and application thereof Download PDFInfo
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Abstract
The invention discloses a platinum (II) complex/sodium deoxycholate hybrid material, which is prepared by self-assembling a cationic platinum (II) complex and sodium deoxycholate in pure water according to a molar ratio of 1: 0.2-1: 2.8. The hybrid material shows remarkable ultraviolet absorption and fluorescence in a solution state. In the complex/sodium deoxycholate hybrid material solution, beta-cyclodextrin and sodium deoxycholate can perform host-object recognition with beta-CD to realize self-assembly, and the ultraviolet absorption and fluorescence of the solution gradually disappear. Therefore, the metal super-amphipathy molecule realizes reversible fluorescence control and can be used as an effective fluorescence biosensor and a soft material with dynamic property and controllable photophysical property.
Description
Technical Field
The invention relates to a hybrid material based on a platinum (II) complex, in particular to a platinum (II) complex/sodium deoxycholate hybrid material and a self-assembly construction method thereof; the invention also relates to the application of the platinum (II) complex/sodium deoxycholate hybrid material as a fluorescent labeling material and a fluorescent biosensor, belonging to a metal luminescent material and a biosensor.
Background
The transition metal platinum (II) complexes having d8The electronic conformation, in fluid solutions and solids, exhibits intense triplet emission, such as long triplet emission lifetimes, high quantum yields, and tunable excited state properties. These platinum (II) complexes with tetragonal planar structures allow intramolecular or intermolecular metal center front orbitals to approach each other, resulting in molecular stacking due to Pt... Pt and π - π interactions, creating new MMLCT excited states and π - π excited states. Whereas the emission of the MMLCT excited state and the pi-pi interaction excited state between the ligands originates from Pt.. In 1974 Lippard et al discovered that tridentate platinum (II) complexes can intercalate with DNA molecules, and have attracted extensive research interest to biologists and chemists. In 1993, a series of platinum (II) complexes taking terpyridine as a ligand are synthesized by Che et al, and the photophysical properties of the platinum (II) complexes are studied, and the platinum (II) complexes are found to have a strong light-emitting phenomenon in a solid state but hardly emit light in a solution state. This is due to the MLCT excited state of the platinum (II) complex andd-dthe energy of the excited states is very similar, and the MLCT state is easy to passd-dExcited state and deactivated. Therefore, it is a great challenge to make platinum (II) complexes emit intense light in dilute solution.
In recent years, the Yam topic group made many efforts to improve the phenomenon of luminescence of platinum (ii) complexes in solution, found that intermolecular stacking of platinum (ii) complexes in solid and solution significantly affects their photophysical properties, and found that platinum (ii) complexes of different counter ions undergo molecular stacking upon changing the solvent composition, changing the distance between Pt.. Yam et al also alter the hydrophilicity of the alkyl chains on the ligands, design a series of novel amphiphilic anionic platinum (II) complexes that aggregate in water by Pt... Pt and π - π stacking, and alter their luminescence by altering the solvent composition.
Most of building units of super-amphipathy molecules (SAs) are organic small molecules and polymers, while metal super-amphipathy molecules have important potential application in the fields of luminescent materials and biosensors, but reports about the metal super-amphipathy molecules are less.
Disclosure of Invention
The invention aims to provide a self-assembly construction method of a platinum (II) complex/sodium deoxycholate hybrid material, aiming at the problem that the existing platinum (II) complex hardly emits light in a solution state;
the invention also aims to research the fluorescence performance, reversible regulation and control performance and the like of the platinum (II) complex/sodium deoxycholate hybrid material, so as to be used as an effective biological fluorescence sensor and a soft material with dynamic property and controllable photophysical property.
Preparation of platinum (II) complex/sodium deoxycholate hybrid material (DCA-1)
The platinum (II) complex/sodium deoxycholate hybrid material (DCA-1) is prepared by self-assembling a cationic platinum (II) complex and sodium Deoxycholate (DCA) in pure water according to a molar ratio of 1: 0.2-1: 2.8.
The structural formula of the cationic platinum (II) complex is as follows:
the structural formula of the sodium Deoxycholate (DCA) is as follows:
the coordination mode of the cationic platinum (II) complex and sodium Deoxycholate (DCA) is as follows:
structure and performance of di-platinum (II) complex/sodium deoxycholate hybrid material (DCA-1)
The structure and luminescence property of the platinum (II) complex/sodium deoxycholate hybrid material prepared by the invention are analyzed and explained by ultraviolet-visible absorption spectrum, emission spectrum and Transmission Electron Microscope (TEM).
1. DCA-1 UV-VIS analysis
FIG. 1 (a) is a UV-VIS spectrum of DCA-1 at different molar ratios. In the figure, a broad absorption peak at 430-520 nm is an MLCT absorption, and an absorption shoulder peak at 550nm is an MMLCT absorption peak generated by the interaction of Pt.. DCA was added dropwise to an aqueous solution (0.2 mmol/L) of the platinum (II) complex, and when the molar ratio of DCA to platinum (II) complex was more than 0.2, the intensity of absorption peaks of MLCT and MMLCT was gradually increased with the addition of DCA, and reached a maximum when the molar ratio of DCA to platinum (II) complex was 2:1, indicating that the platinum (II) complex and DCA were electrostatically bound in a 2:1 mode. Fig. 1 (b) is a plot of the intensity and molar ratio of MMLCT absorption peaks at 550nm (DCA/1 =0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8). It is also described that platinum (II) complexes and DCA electrostatically bind in a 2:1 mode to give metallo-superamphiphilic molecules.
2. DCA-1 emission Spectroscopy
FIG. 2 (a) is a graph showing the emission spectra of DCA-1 at 420nnm excitation for different molar ratios. It can be seen that there is an emission peak at 645nm, which is attributed to the 3MMLCT excited state typical of platinum (ii) complexes, resulting from the Pt... Pt and pi-pi interaction. The intensity of the emission peak increases gradually with the addition of DCA, reaching a maximum at a molar ratio of DCA to platinum (II) complex of 2. Fig. 2 (b) is a monitoring of 645nm fluorescence intensity (DCA/1 =0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8). It can be seen that the 3MMLCT peak has a 16-fold increase in luminous intensity.
3. UV-VISIBLE ABSORPTION SPECTRUM ANALYSIS OF DCA-1/BETA-CD
FIG. 3 (a) is a UV-VIS spectrum of DCA-1/β -CD, where β -CD was added dropwise to an aqueous solution of DCA-1, and the clear solution of DCA-1 slowly became cloudy with the addition of β -CD, indicating that aggregation occurred. In the UV-vis absorption spectrum, it can be seen that the MLCT and MMLCT absorption peak intensities gradually decrease with the addition of β -CD, and finally reach the lowest value at a molar ratio of DCA-1/β -CD of 1:3, the lowest value being consistent with the absorption intensity of an aqueous solution (0.2 mmol/L) of the platinum (II) complex. Fig. 3 (b) is a DCA-1/β -CD monitoring of the shoulder absorption intensity at 550nm (DCA-1/β -CD =0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, 3.0, 3.2, 3.4, 3.6, 3.8). It is evident that a linear slope change occurred at the DCA-1/β -CD molar ratio of 1:1 and at the DCA-1/β -CD molar ratio of 1:2. In summary, it can be seen from the ratio of DCA to β -CD of 1:1.5 that half of DCA coordinates to β -CD in the 1:1 mode and half of DCA coordinates to β -CD in the 1:2 mode.
4. DCA-1/beta-CD emission spectroscopy
FIG. 4 (a) is an emission spectrum of DCA-1/β -CD. As can be seen from the figure, the intensity of the 3MMLCT emission peak at 645nm decreases with the addition of β -CD, and reaches a minimum value when the molar ratio of DCA-1/β -CD is 1:3, which is consistent with the emission intensity of 1 in water (0.2 mmol/L). FIG. 4 (b) is a graph showing the monitoring of fluorescence intensity at 645nm (DCA-1/β -CD =0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, 3.0, 3.2, 3.4, 3.6, 3.8), and it can be seen that the fluorescence intensity decreases with the addition of β -CD and reaches a minimum value when the molar ratio of DCA-1/β -CD is 1: 3. As can be seen from the above, the absorption intensity and emission intensity of DCA-1/β -CD gradually decreased with the addition of β -CD, and were minimized (absorption intensity and emission intensity and fluorescence disappeared) when the molar ratio of DCA-1/β -CD was 1: 3.
In summary, two coordination modes of 1:1 and 2:1 for host-guest recognition between β -CD and DCA are described, namely:
DCA-1 Transmission Electron Microscopy (TEM) analysis
FIG. 5 shows a transmission electron microscope of DCA-1, in which DCA-1 is a rod-like aggregate having a length of several micrometers and a width of about 300 nm.
6. Macroscopic photo analysis
FIG. 6 is a photomicrograph of a 2:1 molar ratio DCA/1, showing that under natural light, it is clearly seen that after DCA is added to an aqueous solution of the platinum (II) complex (FIG. 6 a) (FIG. 6 b), the solution becomes less transparent, indicating that aggregation has occurred. Under 365nm UV light, it can be seen that the solution luminescence intensity after DCA addition (FIG. 6 d) is significantly increased compared to before DCA addition (FIG. 6 c).
In conclusion, the hybrid material formed by electrostatic combination of the platinum (II) complex and sodium deoxycholate can show remarkable ultraviolet absorption and fluorescence in a solution state, obviously improves the phenomenon that the platinum (II) complex hardly emits light in the solution state, and can be applied to the field of fluorescence labeling. Sodium Deoxycholate (DCA) is selected, one is that the sodium Deoxycholate (DCA) has a special amphiphilic structure of a cholate molecule, an anionic surfactant sodium deoxycholate is different from a common alkyl chain surfactant molecule and consists of a steroid ring embedded with hydroxyl and carboxyl, under a proper condition, due to the setback of the steroid ring, the hydroxyl and the carboxyl form a hydrophilic polar surface instead of a single polar head group of the common surfactant, and similarly, the cholate molecule replaces a hydrophobic alkyl chain with the steroid ring, and the amphiphilic structure not only enables the cholate molecule to have specificity on the surface of the cholate molecule, but also can be combined with a platinum (II) complex in an aqueous solution through electrostatic interaction to generate a super-amphiphilic molecule; and secondly, sodium deoxycholate has smaller steric hindrance, so that the reaction is convenient to carry out. Beta-cyclodextrin is added into the hybrid material, sodium deoxycholate can perform host-object recognition with beta-CD to realize de-self-assembly, so that the metal super-amphiphilic molecule realizes reversible fluorescence control, and can be used as an effective fluorescence biosensor and a soft material with dynamic property and controllable photophysical property.
Drawings
FIG. 1 is a graph showing the ultraviolet-visible absorption spectrum (a) of sodium Deoxycholate (DCA) (0.04 mol/L) added dropwise to an aqueous solution (0.2 mmol/L, 2 mL) of a platinum (II) complex and the intensity and molar ratio of the absorption peak of MMLCT at 550nm (b).
FIG. 2 is a graph (a) showing the emission spectrum of sodium deoxycholate-1 under 420nnm excitation and the monitoring (b) of 645nm fluorescence intensity at different molar ratios.
FIG. 3 is a graph of UV-VIS absorption spectrum of sodium deoxycholate-1/β -cyclodextrin (a) and monitoring of shoulder absorption intensity at 550nm by sodium deoxycholate-1/β -cyclodextrin (b).
FIG. 4 shows the emission spectrum (a) of sodium deoxycholate-1/β -cyclodextrin and the monitoring of the fluorescence intensity at 645nm (b).
Fig. 5 is a Transmission Electron Microscope (TEM) of sodium deoxycholate-1 (DCA/1 =1: 2).
FIG. 6 shows photographs (a, c) of a platinum (II) complex, and photographs (b, d) of DCA-1 at a molar ratio of 1:2 of sodium deoxycholate to platinum (II) complex. Wherein c and d are photographs taken under 365nm ultraviolet light irradiation.
Detailed Description
The invention is further described with reference to specific examples.
1. Preparation of platinum (II) complexes
(1) Synthesis of 2, 6-bis (benzimidazolyl) pyridine: to a mixture of 2, 6-dicarboxylpyridine (1.0 g, 5.98 mmol) and o-phenylenediamine (1.29 g, 11.97 mmol) was added 10mL of phosphoric acid, and the mixture was stirred at 230 ℃ for 10 hours. After the reaction is finished, cooling the reaction system to room temperature, adding 200mL of distilled water, adjusting the pH to 9 by using 10% sodium carbonate, and performing suction filtration after solid is separated out to obtain a crude product. The crude product was recrystallized from methanol to give a pure product, 1.58g, in 84.9% yield.1HNMR（DMSO-d6，400MHz）:δ7.27（4H，m），7.71（4H，d），8.12（1H，m），8.29（2H，d）；
(2) Synthesis of ligand L: to a mixture of 2, 6-bis (benzimidazolyl) pyridine (0.31 g, 1 mmol) obtained in step (1) and potassium hydroxide (0.28 g, 5 mmol) was added 30mL of LN, N-dimethylDimethylformamide, after complete dissolution, diethylene glycol-2-bromoethyl methyl ether (0.57 g, 2.5 mmol) was added dropwise and the reaction was stirred at 80 ℃ for 24 hours. After the reaction is finished, cooling the system to room temperature, adding 150mL of distilled water into the reaction mixture, extracting the mixture for multiple times by using dichloromethane, separating an organic layer, and removing the organic solvent by rotary evaporation to obtain a crude product. The obtained crude product was separated by column chromatography (petroleum ether/ethyl acetate = 2/1) to obtain 0.47g of a pure product as colorless viscous liquid with a yield of 78.3%.1HNMR（CDCl3，400MHz）:δ3.28（6H，s），3.35（16H，m），3.72（4H，t），4.92（4H，t），7.32（4H，m），7.53（2H，d），7.83（2H，d），8.03（1H，t），8.31（2H，d）；
(3) Preparation of cationic platinum (II) Complex (1): to a solution of the ligand L (0.42 g, 0.70 mmol) prepared in step (2) in 20mL of dimethyl sulfoxide was added potassium chloroplatinite (K)2PtCl4) (0.27 g, 0.65 mmol), the reaction was stirred at 90 ℃ for 10 hours. And after the reaction is finished, cooling the system to room temperature, and distilling under reduced pressure to remove the solvent dimethyl sulfoxide to obtain a crude product which is a red solid. Dissolving the obtained crude product in distilled water, filtering to remove insoluble substances, dropwise adding four times of ammonium hexafluorophosphate aqueous solution to generate precipitate, filtering, and drying. The dried solid was dissolved in acetone, four times the amount of lithium chloride in acetone was added dropwise to precipitate, and the solution was filtered and dried to obtain 0.47g of pure product as a red solid with a yield of 89.5%.1HNMR（DMSO-d6，400MHz）:δ3.05（6H，s），3.22（12H，m），3.40（4H，t），3.81（4H，t），4.80（4H，t），7.37（4H，m），7.61（2H，d），7.95（2H，d），8.50（1H，t），8.60（2H，d）。
The synthetic route is as follows:
2. preparation of platinum (II) complex/sodium deoxycholate hybrid material (DCA-1)
2mL of 0.2mmol/L cationic platinum (II) complex solution was added dropwise with 20. mu.L of 0.04mol/L (molar ratio of platinum (II) complex to sodium deoxycholate 2: 1) sodium deoxycholate solution (DCA) to form DCA-1 complex having the highest absorption and fluorescence intensities.
3. Disassembly and assembly of platinum (II) complex/sodium deoxycholate hybrid material (DCA-1)
To the aqueous solution of DCA/1 was gradually added dropwise 30. mu.l of a 0.04mol/L β -CD solution (molar ratio of DCA-1 to β -CD: 3.0). With the addition of beta-CD, the absorption intensity and emission intensity of DCA-1 solution gradually decrease, and finally the absorption intensity and emission intensity and fluorescence of the solution disappear.
Claims (5)
1. A platinum (II) complex/sodium deoxycholate hybrid material is prepared by self-assembling a cationic platinum (II) complex and sodium deoxycholate in pure water according to the molar ratio of 1: 2;
the structural formula of the cationic platinum (II) complex is as follows:
the structural formula of the sodium Deoxycholate (DCA) is as follows:
the coordination mode of the cationic platinum (II) complex and sodium deoxycholate is as follows:
2. the platinum (II) complex/sodium deoxycholate hybrid material as defined in claim 1, wherein: the solution state shows remarkable ultraviolet absorption and fluorescence.
3. The platinum (II) complex/sodium deoxycholate hybrid material as defined in claim 1, wherein: adding beta-cyclodextrin into the complex/sodium deoxycholate hybrid material solution, and gradually eliminating the ultraviolet absorption and fluorescence of the solution.
4. The use of the platinum (II) complex/sodium deoxycholate hybrid material as defined in claim 1 as a fluorescent labeling material.
5. The use of the platinum (II) complex/sodium deoxycholate hybrid material as defined in claim 1 as a fluorescence biosensor.
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| CN108774168A (en) * | 2018-06-20 | 2018-11-09 | 西北师范大学 | A kind of application of quinolate supermolecule sensor and its synthesis and fluorescence identifying mercury ion and cyanogen root |
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| CN108774168A (en) * | 2018-06-20 | 2018-11-09 | 西北师范大学 | A kind of application of quinolate supermolecule sensor and its synthesis and fluorescence identifying mercury ion and cyanogen root |
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| Title |
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| 《Reversible luminescence switching accompanied by assembly–disassembly of metallosupramolecular amphiphiles based on a platinum(II) complex†》;Nijuan Liu等;《J. Mater. Chem. C》;20131231;第1卷;第1130-1136页 * |
| Formation of 1D Infinite Chains Directed by Metal−Metal and/or π−π Stacking Interactions of Water-Soluble Platinum(II) 2,6-Bis(benzimidazol-2′-yl)pyridine Double Complex Salts;Victor Chun-Hei Wong et al.;《J. Am. Chem. Soc..》;20180105;第140卷;第657−666页 * |
| Protamine-Induced Supramolecular Self-Assembly of Red-Emissive Alkynylplatinum(II) 2,6-Bis(benzimidazol-2′-yl)pyridine Complex for Selective Label-Free Sensing of Heparin and Real-Time Monitoring of Trypsin Activity;Calford Wai-Ting Chan et al.;《ACS Appl. Mater. Interfaces》;20190822;第11卷;第31585−31593页 * |
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