CN112892592A - A rhodium-based electron mediator [ Cp Rh (bpy) H2O]2+Method for fixing photocatalyst Uio-66-NH2 surface - Google Patents
A rhodium-based electron mediator [ Cp Rh (bpy) H2O]2+Method for fixing photocatalyst Uio-66-NH2 surface Download PDFInfo
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Abstract
本发明公开了一种铑系电子媒介体[Cp*Rh(bpy)H2O]2+固载于光催化剂Uio‑66‑NH2表面的方法，属于光催化剂制备技术领域。本发明通过酰胺化反应将羧酸联吡啶修饰到MOF材料UiO‑66‑NH2表面，再与二氯(五甲基环戊二烯基)合铑(III)二聚体反应，最终将铑系电子媒介体[Cp*Rh(bpy)H2O]2+固载于光催化剂Uio‑66‑NH2表面，将可溶性铑系电子媒介体固载于固体催化剂表面，使均相反应催化剂转变为非均相反应催化剂，实现了铑系电子媒介的回收与再利用，实现铑系电子媒介体的可回收再利用。此外，本发明制备的催化剂在光催化NADH再生反应中表现出优异的催化活性和稳定性。
The invention discloses a method for immobilizing a rhodium-based electron mediator [Cp*Rh(bpy)H 2 O] 2+ on the surface of a photocatalyst Uio-66-NH 2 , and belongs to the technical field of photocatalyst preparation. In the present invention, the carboxylic acid bipyridine is modified on the surface of the MOF material UiO-66-NH 2 by amidation reaction, and then reacts with dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer, and finally the rhodium The electron mediator [Cp*Rh(bpy)H 2 O] 2+ is immobilized on the surface of the photocatalyst Uio-66-NH 2 , and the soluble rhodium-based electron mediator is immobilized on the surface of the solid catalyst, so that the homogeneous reaction catalyst is transformed It is a heterogeneous reaction catalyst, which realizes the recovery and reuse of rhodium-based electronic mediators, and realizes the recovery and reuse of rhodium-based electronic mediators. In addition, the catalyst prepared by the present invention exhibits excellent catalytic activity and stability in the photocatalytic NADH regeneration reaction.
Description
Technical Field
The invention relates to a rhodium-based electron mediator [ Cp + Rh (bpy) H2O]2+Photocatalyst Uio-66-NH2A surface method belongs to the technical field of photocatalyst preparation.
Background
In recent years, enzymatic reactions have been widely used in the chemical synthesis industry. Most of the redox enzyme catalytic reactions require Nicotinamide Adenine Dinucleotide (NADH) as a coenzyme to provide electrons and hydrogen, but the development of the enzyme catalytic reaction in the field of chemical synthesis is limited because NADH is expensive and cannot be recovered. Therefore, in the NADH-dependent enzyme-catalyzed reaction, it is necessary to design an efficient regeneration method to ensure the continuous supply of NADH to the enzyme.
The photocatalytic NADH regeneration process only utilizes solar energy to drive reaction, and the process is green and efficient. The enzyme catalysis uses NADH as a reducing agent, and the NADH is changed into NAD after the reaction+When the enzyme catalytic reaction is combined with photocatalysis, the photocatalyst absorbs photons to generate electron transition, and NAD can be converted+Reducing the NADH into NADH, realizing the regeneration of the NADH, circularly participating in the reaction and reducing the cost of enzyme catalysis reaction. However, the electron energy excited by the photocatalyst is related to the NAD+The energy of the light source is not matched, and an electron mediator is needed to be used as a conveyor belt to transfer electrons excited by the photocatalyst to the NAD+Introduction of NAD into the host cell+Reducing to NADH. The rhodium system electron mediator [ Cp Rh (bpy) H is prepared by the reaction of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer and bipyridine2O]2+Is the most common electronic mediator, has high price, is dissolved in a reaction system in the reaction process and cannot be recycled. Therefore, it is necessary to provide a rhodium-based electron mediator which can be recovered and reused.
Disclosure of Invention
The invention provides a rhodium-based electron mediator [ CpRh (bpy) H for solving the problem that the existing rhodium-based electron mediator can not be recycled2O]2+Photocatalyst Uio-66-NH2A method of surfacing.
A rhodium-based electron mediator [ Cp Rh (bpy) H2O]2+Photocatalyst Uio-66-NH2A method of surfacing, the method comprising the steps of:
step 1, carboxylic acid bipyridyl is immobilized at Uio-66-NH2Surface, obtaining bipyridine amide;
step 2, then the bipyridine amide is combined with dichloro (pentamethylcyclopentadienyl)Rhodium (III) dimer reaction to obtain [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Further, the operation process for preparing the bipyridine amide in the step 1 is as follows: refluxing and reacting carboxylic acid bipyridyl in thionyl chloride solvent for 1-4 h, evaporating to dryness to obtain bipyridyl acyl chloride, and then mixing the bipyridyl acyl chloride with Uio-66-NH2Stirring and reacting in a dichloromethane solvent for 2-12 h, filtering, and drying the obtained solid to obtain the bipyridyl amide.
Further, the carboxylic acid bipyridine is a bipyridine containing a carboxyl group.
Further, the carboxylic acid bipyridine is 2, 2-bipyridine-3-carboxylic acid, 2, 2-bipyridine-4-carboxylic acid, 2, 2-bipyridine-5-carboxylic acid, 2,2 '-bipyridine-3, 3' -dicarboxylic acid, 2,2 '-bipyridine-4, 4' -dicarboxylic acid or 2,2 '-bipyridine-5, 5' -dicarboxylic acid.
Further, the mass-to-volume ratio of the carboxylic acid bipyridyl to the thionyl chloride is 1 mg: (1-5) mL.
Further, the mass-to-volume ratio of the carboxylic acid bipyridyl to the dichloromethane is 1 mg: (1-5) mL.
Further, the reflux reaction temperature in the step 1 is 50-80 ℃.
Further, in step 2, [ Cp + Rh (bpy) H was prepared2O]2+@Uio-66-NH2The operation process comprises the following steps: reacting the bipyridyl amide obtained in the step 1 with dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer in a methanol solvent for 3-24H, filtering, washing and drying after reaction to obtain [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Further, carboxylic acid bipyridine, Uio-66-NH2The mass ratio of the (pentamethylcyclopentadienyl) rhodium (III) dichloride dimer to the (pentamethylcyclopentadienyl) rhodium (III) dichloride dimer is 1 (10-100) to 0.1-1.
Further, the mass-to-volume ratio of the carboxylic acid bipyridyl to methanol is 1 mg: (1-5) mL.
The invention has the following beneficial effects: the invention modifies carboxylic acid bipyridyl into MOF material UiO-66-NH through amidation reaction2Surface, reacting with dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer to obtain rhodium systemElectron mediator [ Cp Rh (bpy) H2O]2+Photocatalyst Uio-66-NH2The surface is that the soluble rhodium-based electronic mediator is immobilized on the surface of the solid catalyst, so that the homogeneous reaction catalyst is converted into a heterogeneous reaction catalyst, the recovery and the reutilization of the rhodium-based electronic mediator are realized, and the recovery and the reutilization of the rhodium-based electronic mediator are realized. The catalyst prepared by the invention shows excellent catalytic activity and stability in the photocatalysis NADH regeneration reaction.
Drawings
FIG. 1 shows [ Cp. multidot. Rh (bpy) H obtained in example 12O]2+@Uio-66-NH2SEM picture of (a);
FIG. 2 shows [ Cp. multidot. Rh (bpy) H obtained in example 12O]2+@Uio-66-NH2The yield of the photocatalytic NADH regeneration experiment;
FIG. 3 shows [ Cp + Rh (bpy) H obtained in example 12O]2+@Uio-66-NH2NADH yield when used repeatedly.
Detailed Description
The experimental procedures used in the following examples are conventional unless otherwise specified. The materials, reagents, methods and apparatus used, unless otherwise specified, are conventional in the art and are commercially available to those skilled in the art.
Example 1:
dissolving 2mg of 2, 2-bipyridine-5-carboxylic acid in 5mL of thionyl chloride, refluxing at 60 ℃ for 1h, evaporating to dryness, adding 2mL of dichloromethane and 50mg of photocatalyst Uio-66-NH2Stirring for 4h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 2mL of methanol, adding 2mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 12h, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Obtaining [ Cp Rh (bpy) H2O]2+@Uio-66-NH2The scanning electron microscope results are shown in FIG. 1, and it can be seen from FIG. 1 that the obtained material has regular morphologyThe regular octahedron has uniform size and good dispersibility. The contents of the respective elements are shown in table 1 below.
TABLE 1[ Cp Rh (bpy) H2O]2+@Uio-66-NH2The content of each element in the
[ Cp Rh (bpy) H obtained by applying this example2O]2+@Uio-66-NH2Photocatalytic NADH regeneration:
the total volume of the reaction solution was 2mL, including a phosphate buffer concentration of 20mmol/L, NAD+Concentration 1mmol/L, catalyst [ Cp Rh (bpy) H2O]2+@Uio-66-NH22 mg; irradiating under 300W xenon lamp for 20min, and measuring the absorption wavelength at 340nm with ultraviolet-visible spectrophotometer every 5min to determine NADH yield. The result of the photocatalytic NADH regeneration yield is shown in FIG. 2, and it can be seen from FIG. 2 that the NADH yield gradually increases with the increase of the illumination time, and reaches 98% when the illumination time is 20 min. .
And (3) recycling the catalyst:
after the reaction, the catalyst [ CpRh (bpy) H was collected by centrifugation2O]2+@Uio-66-NH2After drying, the catalytic experiment was repeated 4 times, the experimental results are shown in fig. 3, and it can be seen from fig. 3 that the catalyst [ Cp × rh (bpy) H2O]2+@Uio-66-NH2Has good stability, the catalytic effect is not obviously changed in the recycling process, and the NADH yield is over 95 percent. .
Example 2:
2mg of 2, 2-bipyridine-5-carboxylic acid was dissolved in 2mL of thionyl chloride, refluxed at 50 ℃ for 4 hours and then evaporated to dryness, and 2mL of dichloromethane and 20mg of photocatalyst Uio-66-NH were added thereto2Stirring for 2h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 2mL of methanol, adding 0.2mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 24h, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ alpha ]Cp*Rh(bpy)H2O]2+@Uio-66-NH2。
Example 3:
2mg of 2, 2-bipyridine-5-carboxylic acid was dissolved in 10mL of thionyl chloride, refluxed at 80 ℃ for 4 hours and evaporated to dryness, and 10mL of dichloromethane and 200mg of a photocatalyst Uio-66-NH were added thereto2Stirring for 6h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 6mL of methanol, adding 1mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 3 hours, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Example 4:
2mg of 2, 2-bipyridine-3-carboxylic acid was dissolved in 4mL of thionyl chloride, refluxed at 70 ℃ for 1 hour, evaporated to dryness, and 4mL of dichloromethane and 100mg of photocatalyst Uio-66-NH were added thereto2Stirring for 10h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 8mL of methanol, adding 1mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 10 hours, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Example 5:
2mg of 2, 2-bipyridine-4-carboxylic acid was dissolved in 6mL of thionyl chloride, refluxed at 60 ℃ for 2 hours and then evaporated to dryness, and 10mL of dichloromethane and 200mg of a photocatalyst Uio-66-NH were added thereto2Stirring for 8h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 10mL of methanol, adding 1.5mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 8 hours, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Example 6:
2mg of 2,2 '-bipyridine-3, 3' -dicarboxylic acid was dissolved in 3mL of thionyl chloride, refluxed at 70 ℃ for 3 hours, evaporated to dryness, and 7mL of diMethyl chloride and 30mg photocatalyst Uio-66-NH2Stirring at normal temperature for 12h, filtering and drying; ultrasonically dispersing the obtained solid in 7mL of methanol, adding 0.5mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 16h, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Example 7:
2mg of 2,2 '-bipyridine-4, 4' -dicarboxylic acid was dissolved in 8mL of thionyl chloride, refluxed at 60 ℃ for 1 hour and then evaporated to dryness, and 3mL of dichloromethane and 160mg of photocatalyst Uio-66-NH were added thereto2Stirring for 7h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 4mL of methanol, adding 0.8mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 6 hours, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Example 8:
2mg of 2,2 '-bipyridine-5, 5' -dicarboxylic acid was dissolved in 7mL of thionyl chloride, refluxed at 50 ℃ for 4 hours and then evaporated to dryness, and 8mL of dichloromethane and 80mg of a photocatalyst Uio-66-NH were added thereto2Stirring for 5h at normal temperature, filtering and drying; ultrasonically dispersing the obtained solid in 5mL of methanol, adding 1.2mg of dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer, stirring at normal temperature for 9h, filtering and drying to obtain Uio-66-NH2Immobilized [ Cp Rh (bpy) H2O]2+Metal mediator [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
Claims (10)
1. A rhodium-based electron mediator [ Cp Rh (bpy) H2O]2+Photocatalyst Uio-66-NH2A method of surfacing, characterized in that the method comprises the steps of:
step 1, carboxylic acid bipyridyl is immobilized at Uio-66-NH2Surface, obtaining bipyridine amide;
step 2Then reacting the bipyridylamide with dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer to obtain [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
2. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 12O]2+Photocatalyst Uio-66-NH2The surface method is characterized in that the operation process for preparing the bipyridyl amide in the step 1 is as follows: refluxing and reacting carboxylic acid bipyridyl in thionyl chloride solvent for 1-4 h, evaporating to dryness to obtain bipyridyl acyl chloride, and then mixing the bipyridyl acyl chloride with Uio-66-NH2Stirring and reacting in a dichloromethane solvent for 2-12 h, filtering, and drying the obtained solid to obtain the bipyridyl amide.
3. The rhodium-based electron mediator [ Cp + Rh (bpy) H according to claim 1 or 22O]2+Photocatalyst Uio-66-NH2The surface method is characterized in that the carboxylic acid bipyridyl is bipyridyl containing carboxyl.
4. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 32O]2+Photocatalyst Uio-66-NH2A method for the preparation of a surface, characterized in that the carboxylic acid bipyridine is 2, 2-bipyridine-3-carboxylic acid, 2, 2-bipyridine-4-carboxylic acid, 2, 2-bipyridine-5-carboxylic acid, 2,2 '-bipyridine-3, 3' -dicarboxylic acid, 2,2 '-bipyridine-4, 4' -dicarboxylic acid or 2,2 '-bipyridine-5, 5' -dicarboxylic acid.
5. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 22O]2+Photocatalyst Uio-66-NH2The surface method is characterized in that the mass-volume ratio of the carboxylic acid bipyridyl to the thionyl chloride is 1 mg: (1-5) mL.
6. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 22O]2+Photocatalyst Uio-6 fixed on6-NH2The surface method is characterized in that the mass-volume ratio of the carboxylic acid bipyridyl to the dichloromethane is 1 mg: (1-5) mL.
7. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 22O]2+Photocatalyst Uio-66-NH2The surface method is characterized in that the reflux reaction temperature in the step 1 is 50-80 ℃.
8. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 22O]2+Photocatalyst Uio-66-NH2A method for preparing a surface, characterized in that [ Cp Rh (bpy) H is prepared in step 22O]2+@Uio-66-NH2The operation process comprises the following steps: reacting the bipyridyl amide obtained in the step 1 with dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer in a methanol solvent for 3-24H, filtering, washing and drying after reaction to obtain [ Cp Rh (bpy) H2O]2+@Uio-66-NH2。
9. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 82O]2+Photocatalyst Uio-66-NH2The method for preparing the surface is characterized in that the carboxylic acid bipyridyl Uio-66-NH2The mass ratio of the (pentamethylcyclopentadienyl) rhodium (III) dichloride dimer to the (pentamethylcyclopentadienyl) rhodium (III) dichloride dimer is 1 (10-100) to 0.1-1.
10. The rhodium-based electron mediator [ CpRh (bpy) H ] according to claim 82O]2+Photocatalyst Uio-66-NH2The surface method is characterized in that the mass-volume ratio of the carboxylic acid bipyridyl to the methanol is 1 mg: (1-5) mL.
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| CN114685802A (en) * | 2022-03-31 | 2022-07-01 | 国家纳米科学中心 | Silicon-based covalent organic framework photoelectrode and preparation method and application thereof |
| CN116003480A (en) * | 2022-12-30 | 2023-04-25 | 中国科学院赣江创新研究院 | Method for photochemically regenerating coenzyme NADH |
| CN116328844A (en) * | 2023-02-28 | 2023-06-27 | 河北工业大学 | Preparation method and application of core-shell hollow sphere heterojunction photocatalyst using covalent organic framework material to immobilize rhodium electron mediator |
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| JP2016159289A (en) * | 2015-03-05 | 2016-09-05 | トヨタ自動車株式会社 | Light absorption material |
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| JP2016159289A (en) * | 2015-03-05 | 2016-09-05 | トヨタ自動車株式会社 | Light absorption material |
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| YIZHOU WU: "Synergy of Electron Transfer and Electron Utilization via Metal-Organic Frameworks as an Electron Buffer Tank for Nicotinamide Regeneration", 《ACS CATALYSIS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114685802A (en) * | 2022-03-31 | 2022-07-01 | 国家纳米科学中心 | Silicon-based covalent organic framework photoelectrode and preparation method and application thereof |
| CN116003480A (en) * | 2022-12-30 | 2023-04-25 | 中国科学院赣江创新研究院 | Method for photochemically regenerating coenzyme NADH |
| CN116328844A (en) * | 2023-02-28 | 2023-06-27 | 河北工业大学 | Preparation method and application of core-shell hollow sphere heterojunction photocatalyst using covalent organic framework material to immobilize rhodium electron mediator |
| CN116328844B (en) * | 2023-02-28 | 2024-04-26 | 河北工业大学 | Preparation method and application of core-shell hollow sphere heterojunction photocatalyst constructed by utilizing rhodium electronic medium fixed by covalent organic framework material |
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