CN111239110B - Construction method of porphyrin derivative with aggregation-induced emission performance applied to electrochemiluminescence system - Google Patents
Construction method of porphyrin derivative with aggregation-induced emission performance applied to electrochemiluminescence system Download PDFInfo
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Abstract
The invention discloses a method for constructing an electrochemiluminescence system by applying porphyrin derivatives with aggregation-induced emission performance, which comprises the steps of treating a bare glassy carbon electrode, thoroughly drying the electrode, and then using a coreactant K and an electrochemiluminescence reagent TPP-TPE2S2O8Dissolved in phosphate buffer solution, a glassy carbon electrode is taken as a working electrode, and a platinum electrode and an Ag/AgCl electrode are respectively taken as a counter electrode and a reference electrode and are immersed in a water phase. The electrochemical luminescence system is easy to construct, the used luminescent agent is less in dosage, the generated ECL signal is strong, and the stability and the reproducibility are better; the luminescent molecule is in DMF/H2When the water content in the O mixed solvent is increased from 0% to 90%, the fluorescence emission spectrum and ECL emission are gradually enhanced, compared with amino porphyrin, TPP-TPE is not easy to aggregate in a water phase, the water solubility is better, the ECL emission is enhanced by 6 times,the luminous efficiency and the sensitivity are obviously improved.
Description
Technical Field
The invention belongs to the technical field of electrochemical luminescence system construction, and particularly relates to a construction method of applying porphyrin derivatives with aggregation-induced emission performance to an electrochemical luminescence system.
Background
Porphyrin has excellent photoelectric properties and is widely researched, and as a better electrochemical luminescent material, porphyrin has a strong luminescent signal in an organic phase, and has good luminescent stability and high sensitivity. In the field of electrochemiluminescence research, most porphyrin compounds have poor solubility in a water phase, and an aggregate is easily formed among molecules to cause fluorescence quenching, so that the luminous efficiency is low; this greatly limits the study of porphyrin compounds in the field of electrochemiluminescence. Although studies have reported that water solubility and luminous efficiency of porphyrins are improved by physical and chemical means, such as hydrogel-coated porphyrins and supramolecules constructed by combining cyclodextrins with porphyrins, these methods cannot effectively solve pi-pi stacking between porphyrin molecules, and the luminous mechanism cannot be accurately explained.
Disclosure of Invention
The invention aims to solve the problems and provides a construction method for applying a porphyrin derivative with aggregation-induced emission performance to an electrochemiluminescence system.
The purpose of the invention is realized by the following technical scheme:
a process for preparing the porphyrin derivative with aggregation-induced emission performance used as electrochemical luminous system includes such steps as treating bare glassy carbon electrode, thoroughly drying, and reacting with the porphyrin derivative TPP-TPE and co-reactant K2S2O8Dissolved in phosphate buffer solution, a glassy carbon electrode is taken as a working electrode, and a platinum electrode and an Ag/AgCl electrode are respectively taken as a counter electrode and a reference electrode and are immersed in a water phase.
Further, the construction method specifically comprises the following steps:
(1) polishing the glassy carbon electrode, and then drying by using nitrogen;
(2) dissolving 1.05mg of synthesized TPP-TPE in 1mL of DMF to prepare a solution of 1 mmol/L;
(3) dripping 75 mu L of TPP-TPE solution obtained in the step (2) to 5mL of solution containing K2S2O8In the phosphate buffer solution, a glassy carbon electrode is used as a working electrode, and a platinum electrode and an Ag/AgCl electrode are respectively used as a counter electrode and a reference electrode to be immersed in a water phase.
Furthermore, in the step (1), the glassy carbon electrode is treated by the following steps: with 0.3 μm and 0.05 μm Al in this order2O3Grinding the powder, and then sequentially washing with ultrapure water, ethanol and ultrapure water.
Further, in step (3), the co-reactant K2S2O8The concentration of (2) was 0.1mol/L, and the pH of the phosphate buffer was 7.5.
Furthermore, the potential scanning rate of the system constructed by the method is 0.1 V.s-1The potential window is-1.7 to-0.1V.
The invention has the following beneficial effects:
compared with the prior art, the construction method of the porphyrin derivative with aggregation-induced emission performance applied to the electrochemical luminescence system has the following advantages:
(1) the electrochemical luminescence system is easy to construct, the used luminescent agent is less in dosage, the generated ECL signal is strong, and the stability and the reproducibility are better;
(2) the luminescent molecule is in DMF/H2When the water content in the O mixed solvent is increased from 0% to 90%, the fluorescence emission spectrum and ECL emission are gradually enhanced, and compared with amino porphyrin, TPP-TPE is not easy to aggregate in a water phase, the water solubility is good, the ECL emission is enhanced by 6 times, and the luminous efficiency and the sensitivity are obviously improved.
Drawings
FIG. 1(a) shows TPP-TPE in DMF/H2Fluorescence emission spectrum of O mixed solvent with increasing water content from 0% to 90%, FIG. 1(b) is amino porphyrinQuinoline in DMF/H2Fluorescence emission spectra in the O mixed solvent increased with water content from 0% to 90%.
FIG. 2 shows TPP-TPE (1.5X 10)-5M) and amino porphyrin (1.5X 10)-5M) in each case at the coreactant K2S2O8And (3) electrochemical luminescence intensity diagram under the system.
FIG. 3 shows TPP-TPE/K2S2O8ECL stability test of the system at first 650 s.
FIG. 4(a), FIG. 4(b), FIG. 4(c), FIG. 4(d) are TPP-TPE/K2S2O8Sweeping speed, potential window, K of the system2S2O8Concentration, pH condition of the buffer solution.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of illustration and description, and is in no way intended to limit the invention.
Examples TPP-TPE are synthesized in the Journal of the Serbian Chemical Society,2008,73(1), in the amino porphyrin references Ma X, Wu Y, Devianamini S, in the Journal of GO-COOH/AuNPs/ZnAPTPP nanocomposites based on the pi-pi coupling, in the concrete interface for low-potential photo Chemical sensing of 4-nitro phenol [ J ]. Talantan, 2018,178: 969, and by Wang L, Feng Y, et al.
Example 1
A method for constructing an electrochemiluminescence system by applying porphyrin derivatives with aggregation-induced emission performance comprises the following steps:
(1) the glassy carbon electrode was successively coated with 0.3 μm and 0.05 μm Al2O3Grinding the powder, then sequentially washing the powder with ultrapure water, ethanol and ultrapure water, and drying the powder with nitrogen.
(2) 1.05mg of synthesized TPP-TPE is dissolved in 1mL of DMF to prepare a solution of 1 mmol/L.
(3) Dripping 75 mu L of TPP-TPE solution obtained in the step (2) into 5mL of solution containing K2S2O8In a phosphate buffer solution of (2), the pH value is 7.5, K2S2O8The concentration of (2) is 0.1 mol/L.
(4) And (2) taking the glassy carbon electrode polished in the step (1) as a working electrode, inserting the working electrode into the solution, and respectively taking a platinum electrode and an Ag/AgCl electrode as a counter electrode and a reference electrode to be inserted into the solution.
Detection was carried out using an MPI-A type capillary electrophoresis-electrochemiluminescence analyzer (purchased from Sierra Mimey Analyzer, Ltd.) with a photomultiplier tube bias set at 800V.
Example 2
FIG. 1 determination of TPP-TPE and amino porphyrin in DMF/H2Fluorescence emission spectrum when the water content in the O mixed solvent increases from 0% to 90%. TPP-TPE and amino porphyrin concentrations were 1.5X 10-5mol/L，DMF/H 20 Total volume of 5mL, change DMF/H only2Water content in the O mixed solvent. The fluorescence detector is Agilent G9800A. The results are shown in FIG. 1. The results show that TPP-TPE is in DMF/H2When the water content in the O mixed solvent is increased from 0% to 90%, the fluorescence emission spectrum is gradually enhanced, and compared with amino porphyrin, TPP-TPE is not easy to aggregate in a water phase and has better water solubility.
2. Determination of TPP-TPE (1.5X 10)-5mol/L) and amino porphyrin (1.5X 10)-5mol/L) in the respective coreactant K2S2O8Electrochemiluminescence intensity under the system. The construction method of the system is the same as that of example 1, and the coreactant K in the system constructed by the method2S2O8Has a concentration of 0.1mol/L, a pH of 7.5 in a phosphate buffer, and a potential sweep rate of 0.1 V.s-1The potential window is-1.7 to-0.1V. The results are shown in FIG. 2. The results show that the electrochemical luminescence intensity of TPP-TPE is about 6 times of that of amino porphyrin.
3.TPP-TPE/K2S2O8ECL stability testing of the System at the first 650s, the same as the System built in example 1, with the co-reactant K2S2O8Has a concentration of 0.1mol/L, a pH of 7.5 in a phosphate buffer, and a potential sweep rate of 0.1 V.s-1The potential window is-1.7 to-0.1And V. The results are shown in FIG. 3. The results show a relative standard deviation of 0.2%, indicating TPP-TPE/K2S2O8The luminescent system has better stability and reproducibility.
4. For TPP-TPE (1.5X 10)-5mol/L)/K2S2O8Sweeping speed, potential window, K of the system2S2O8The conditions such as concentration, pH value of phosphate buffer solution and the like are optimized, and the construction method of the system is similar to that of the embodiment 1. The results are shown in FIG. 4. The results show that the optimum sweeping speed is 0.1 V.s-1The optimal potential window is-1.7 to-0.1V, K2S2O8The optimal concentration is 0.1mol/L, and the optimal pH value of the phosphate buffer solution is 7.5.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (5)
1. A method for constructing an electrochemiluminescence system by using porphyrin derivatives with aggregation-induced emission performance is characterized in that a bare glassy carbon electrode is treated and then thoroughly dried, and then an electrochemiluminescence reagent, namely porphyrin derivative TPP-TPE and a coreactant K, is used2S2O8Dissolved in phosphate buffer solution, a glassy carbon electrode is taken as a working electrode, and a platinum electrode and an Ag/AgCl electrode are respectively taken as a counter electrode and a reference electrode and are immersed in a water phase.
2. The method for constructing the electrochemiluminescence system by using the porphyrin derivative with aggregation-induced emission property according to claim 1, wherein the method comprises the following steps:
(1) polishing the glassy carbon electrode, and then drying by using nitrogen;
(2) dissolving 1.05mg of synthesized TPP-TPE in 1mL of DMF to prepare a solution of 1 mmol/L;
(3) dripping 75 mu L of TPP-TPE solution obtained in the step (2) into 5mL of solution containing K2S2O8In the phosphate buffer solution, a glassy carbon electrode is used as a working electrode, and a platinum electrode and an Ag/AgCl electrode are respectively used as a counter electrode and a reference electrode to be immersed in a water phase.
3. The method for constructing an electrochemiluminescence system from porphyrin derivatives with aggregation-induced emission properties according to claim 2, wherein in the step (1), the glassy carbon electrode is treated by the following steps: with 0.3 μm and 0.05 μm Al in this order2O3Grinding the powder, and then sequentially washing with ultrapure water, ethanol and ultrapure water.
4. The method for constructing an electrochemiluminescence system by using the porphyrin derivative with aggregation-induced emission property as claimed in claim 2, wherein in the step (3), the co-reactant K is2S2O8The concentration of (2) was 0.1mol/L, and the pH of the phosphate buffer was 7.5.
5. The method for constructing an electrochemiluminescence system by using the porphyrin derivative with aggregation-induced emission properties according to claim 2, wherein the potential scanning rate of the system constructed by the method is 0.1V-s-1The potential window is-1.7 to-0.1V.
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| CN112812766B (en) * | 2020-12-30 | 2023-08-08 | 广州大学 | Application of compound in preparation of electrochemiluminescence material and electrochemiluminescence device |
| CN112852410A (en) * | 2021-01-11 | 2021-05-28 | 广州大学 | Electrochemiluminescence active particles and preparation method and application thereof |
| CN113189160B (en) * | 2021-05-14 | 2023-09-01 | 西北师范大学 | Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion |
| CN113189161B (en) * | 2021-05-18 | 2023-06-23 | 西北师范大学 | Construction method of aqueous phase electrochemical luminescence system based on 9-phenyl-9-H-carbazole |
| CN114113277A (en) * | 2021-10-21 | 2022-03-01 | 西北师范大学 | Method for constructing electrochemical luminescence system by using luminescent compound |
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