CN113136199B - Continuous two-step energy transfer light capture system and preparation method and application thereof - Google Patents
Continuous two-step energy transfer light capture system and preparation method and application thereof Download PDFInfo
- Publication number
- CN113136199B CN113136199B CN202110437362.7A CN202110437362A CN113136199B CN 113136199 B CN113136199 B CN 113136199B CN 202110437362 A CN202110437362 A CN 202110437362A CN 113136199 B CN113136199 B CN 113136199B
- Authority
- CN
- China
- Prior art keywords
- compound
- mol
- acceptor
- light
- energy transfer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention belongs to the field of luminescent materials of light capture systems, and particularly relates to a continuous two-step energy transfer artificial light capture system, a preparation method and application thereof, and particularly relates to a ureidopyrimidone functionalized tetraphenylethylene compound C serving as an AIE type energy donor and polymerized into a hydrogen bond supermolecule polymer through quadruple hydrogen bonds, a hydrophobic fluorescent dye DBT serving as a relay acceptor A and NDI serving as a final acceptor B, and CTAB serving as an amphiphile for wrapping the donor and the two acceptors through a micro emulsification method to prepare water-soluble light capture nano particles. The beneficial effects of the light capture system are as follows: has water dispersibility; the structure of the nano particles is stable; the quadruple hydrogen bond effect and the hydrophobic effect jointly promote and enhance the AIE effect, so that the two-step energy transfer has the efficient antenna effect; the system has adjustable luminescent color and can be prepared into white light emitting materials.
Description
Technical Field
The invention belongs to the field of luminescent materials of light capture systems, and particularly relates to an artificial light capture system with secondary energy transfer and a preparation method and application thereof.
Background
Photosynthesis is the basis of all life activities on the earth, and the process of photosynthesis includes two important steps, absorption of solar energy and conversion of solar energy into chemical energy. The light collection system plays an important role in converting light energy into chemical energy in natural photosynthesis, and opens up a wide prospect for developing renewable energy sources. Light trapping systems (LHSs) in nature are complex supramolecular assemblies that contain hundreds of chlorophyll molecules, are capable of efficiently trapping light and transferring excitation energy to receptors in reaction centers through multi-step energy transfer. The supramolecular polymer is a monomer array connected together through non-covalent action, and is an ideal platform for constructing artificial LHS (luteinizing hormone releasing substance) because of the advantages of simple preparation, dynamic reversibility and the like.
Currently, most research is focused on constructing a single-step energy transfer light trapping system in organic solvents. This is because: (1) Since the energy donor is generally hydrophobic, organic systems can avoid aggregation-induced quenching effects (ACQ) caused by the aqueous phase; and (2) the single-step energy transfer system is easy to construct. Therefore, most of the systems only comprise a one-step direct fluorescence resonance energy transfer process from a donor to a receptor, and the natural light acquisition system with excellent efficiency has the characteristic of multi-channel information communication. Therefore, in order to better understand and simulate natural lighting antenna systems and to be applied in practice, it is highly desirable to establish a multi-step energy transfer light capture system with the capability of converting solar energy into chemical energy in an aqueous environment.
Disclosure of Invention
The invention aims to provide a preparation method and application of a continuous two-step energy transfer light capture system.
The technical scheme provided by the invention is as follows:
the invention provides a continuous energy transfer light capture system, which utilizes a compound C as a light acquisition antenna and an energy donor, a compound A as a relay acceptor and a compound B as a final acceptor, and in the presence of an amphiphilic surfactant, the compound C, the compound A, the compound B and the surfactant are subjected to micro-emulsification in an aqueous solution to form nano particles so as to construct the light capture system;
wherein the chemical structure of compound C is as follows:
the chemical formula of compound a (DBT) is as follows:
the chemical structure of compound B (NDI) is as follows:
further, the surfactant is cetyl trimethyl ammonium bromide CTAB.
Further, the molar concentration ratio of compound a to compound C is constant at 50.
The compound C forms a supramolecular polymer in organic solvents such as chloroform, dichloromethane and the like, and monomers are connected through quadruple hydrogen bonds:
the supermolecule polymer is added into 1mM CTAB aqueous solution by a micro-emulsification method and is subjected to ultrasonic treatment to prepare water-phase dispersed nano particles, and the C has tetraphenylethylene groups and aggregation-induced emission properties, so that the prepared nano particles show blue fluorescence.
The acceptor molecules are simultaneously doped into the nano particles to prepare the light capture system with energy transfer, and the emission spectrum of C and the absorption spectrum of A, the emission spectrum of A and the absorption spectrum of B are better overlapped when A and B are selected as the relay acceptor and the final acceptor respectively, so that the generation of fluorescence resonance energy transfer is facilitated.
The light capture system is characterized in that the molar concentration ratio of the donor compound C to the relay acceptor compound A to the final acceptor B is 25000:1 to 2500; the concentration ranges are in the following intervals: concentration of Compound C1X 10 -6 ~1×10 -4 mol/L, concentration of Compound A1X 10 -9 mol/L-1×10 -6 mol/L, concentration of Compound B1X 10 -9 mol/L-1×10 -6 mol/L。
The light capture system is characterized in that when the molar concentration ratio of the donor compound C to the relay acceptor compound A to the final acceptor B is 1500.
The invention also provides the application of the light trapping system in luminescent materials.
The invention also provides the application of the light capture system in white light materials.
Furthermore, the molar concentration ratio of compound a, compound B, and compound C was 6.
The invention also provides a preparation method of the light capture system, which comprises the following steps:
and weighing the compound C, the compound A and the compound B according to a set molar concentration ratio, uniformly mixing, adding into a surfactant aqueous solution, and performing ultrasonic treatment to form a uniformly dispersed nanoparticle aqueous solution to obtain a light capture system.
Further, the concentration of the surfactant aqueous solution is 1.0mmol/L.
Further, the compound C, the compound A and the compound B are dissolved in a hydrophobic organic solvent and uniformly mixed.
Further, the hydrophobic organic solvent is selected from one or more of chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane.
The beneficial effects of the invention are embodied in the following aspects:
(1) The light capture system is constructed in aqueous solution, has the effects of low cost, environmental protection and no pollution, is in the form of water dispersible nanoparticles, has the characteristic of stable structure, and still has high-efficiency light-emitting characteristic after being stored for months;
(2) The light capture system has two continuous energy transfer processes, and can better simulate the energy transfer path of photosynthesis in the nature;
(3) The selected energy donor molecules have Aggregation Induced Emission (AIE) capability, fluorescence quenching caused by the formation of nanoparticles is avoided, and the AIE effect is enhanced due to quadruple hydrogen bond polymerization and hydrophobic aggregation;
(4) The optical trapping system can still better transfer energy under the condition of very high donor-acceptor ratio, a unit acceptor can bear the energy transferred by a donor in an amount which is hundreds or even thousands of times, and the optical trapping system has the advantages of high-efficiency energy transfer capability, ultrahigh antenna effect and the like, the highest efficiency of the first step of energy transfer (from a compound C to a compound A) reaches 87.4 percent, the highest antenna effect reaches 27.8 percent, the highest efficiency of the second step of energy transfer (from the compound A to the compound B) reaches 83.4 percent, the highest total antenna effect reaches 63.1, and the secondary energy transfer antenna effect which is more than that reported in the prior literature is generally lower than 20;
(5) The fluorescence change trend of the light capture system just comprises a white light emission band, and the high-efficiency white light emission material can be prepared.
Drawings
FIG. 1 shows fluorescence spectra of donor compound C and relay acceptor compound A in aqueous solution at different ratios.
FIG. 2 shows fluorescence spectra of donor compound C, relay acceptor compound A and final acceptor compound B in aqueous solution in different ratios.
FIG. 3 is a CIE 1931 color coordinate diagram at different acceptor levels.
Fig. 4 is a white light emission fluorescence spectrum for donor concentration ratio 1500.
Detailed Description
The present invention will now be further described with reference to specific examples, which are intended to be illustrative and not limiting of the invention, and any number of variations of the invention, which would achieve similar results and which would be apparent to those skilled in the art, are intended to be encompassed by the present invention.
Example 1
Weighing 96.4mg of compound C into a 10mL volumetric flask, adding dichloromethane to the volumetric flask until the volume is 10mL, and preparingMaking into 1 × 10 - 2 mol/L mother liquor. 182.23mg hexadecylammonium bromide was weighed into a 500mL volumetric flask, and then diluted to 500mL with deionized water to prepare an aqueous solution having a concentration of 1.0mmol/L (this solution was named CTAB aqueous solution). Weighing 5.98mg of compound A into a 10mL volumetric flask, adding dichloromethane to a constant volume of 10mL, and preparing into 2X 10 -3 Preparing 4X 10 mol/L mother liquor by taking 200 mu L mother liquor to a 10mL volumetric flask with a pipette -5 And (4) mol/L diluent. 250 μ L of 4X 10 solution was taken by pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 Putting the compound C solution of mol/L into a 10mL conical flask, adding 10mL CTAB aqueous solution of 10mL, performing ultrasonic treatment for 30min, and continuously shaking during the ultrasonic treatment to prepare the nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 50 -5 mol/L, concentration of Relay acceptor Compound A1X 10 - 6 And mol/L, measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 87 percent, and the antenna effect is 12.6 percent.
Example 2
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 166. Mu.L of the aqueous solution was taken out with a pipette at a concentration of 4X 10 -5 mol/L Compound A dilution and a 50uL concentration of 1X 10 -2 And (3) carrying out ultrasonic treatment for 30min by using a mol/L compound C solution, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 75 -5 mol/L, concentration of Relay acceptor Compound A6.66X 10 -7 And measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 79 percent, and the antenna effect is 18.2.
Example 3
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 125. Mu.L of a 4X 10-concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50uL concentration 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 100, wherein the concentration of the donor compound C is 5 x 10 -5 mol/L, concentration of Relay acceptor Compound ADegree of 5X 10 -7 And mol/L, measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 69 percent, and the antenna effect is 22.2.
Example 4
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 100. Mu.L of a 4X 10 concentrated solution was taken out with a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 125 -5 mol/L, concentration of Relay acceptor Compound A4X 10 -7 And (3) measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 60 percent, and the antenna effect is 23.9 percent.
Example 5
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 75. Mu.L of a 4X 10-concentrated solution was taken out with a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 166 -5 mol/L, concentration of Relay acceptor Compound A3X 10 -7 And measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 56 percent, and the antenna effect is 25.8 percent.
Example 6
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 62.5. Mu.L of a 4X 10 concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (2) carrying out ultrasonic treatment on a compound C solution in mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of a donor compound C to a relay acceptor A being 200, wherein the concentration of the donor compound C is 5 x 10 -5 mol/L, concentration of Relay acceptor Compound A2.5X 10 -7 And the fluorescence intensity of the sample is measured by a fluorescence spectrophotometer, the energy transfer efficiency is 49%, and the antenna effect is 26.7.
Example 7
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 50. Mu.L of a 4X 10 concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 250 -5 mol/L, concentration of Relay acceptor Compound A2X 10 -7 And measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 44 percent, and the antenna effect is 27.6 percent.
Example 8
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 42. Mu.L of a 4X 10-concentrated solution was taken out with a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 300 -5 mol/L, concentration of Relay acceptor Compound A1.67X 10 -7 And (3) measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 40 percent, and the antenna effect is 27.8 percent.
Example 9
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 31. Mu.L of a 4X 10-concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 400, wherein the concentration of the donor compound C is 5 x 10 -5 mol/L, concentration of Relay acceptor Compound A1.25X 10 -7 And mol/L, measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 31 percent, and the antenna effect is 27.3.
Example 10
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 16.7. Mu.L of a 4X 10 solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 Subjecting the compound C solution to ultrasonic treatment for 30min while shakingAnd (3) preparing a nanoparticle aqueous solution with a concentration ratio of the donor compound C to the relay acceptor A of 750, wherein the concentration of the donor compound C is 5 x 10 -5 mol/L, concentration of Relay acceptor Compound A6.67X 10 -8 And (3) measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 27%, and the antenna effect is 26.6.
Example 11
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 12.5. Mu.L of a 4X 10 concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment on a compound C solution of mol/L for 30min, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A being 1000, wherein the concentration of the donor compound C is 5 x 10 -5 mol/L, concentration of Relay acceptor Compound A5X 10 -8 And mol/L, measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 22 percent, and the antenna effect is 23.5 percent.
Example 12
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 4.2. Mu.L of a 4X 10-concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 And (3) carrying out ultrasonic treatment for 30min by using a compound C solution of mol/L, and continuously shaking the compound C solution during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A of 3000 -5 mol/L, concentration of Relay acceptor Compound A1.67X 10 -8 And (3) measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 16%, and the antenna effect is 16.2.
Example 13
Weighing 5.2mg of compound B into a 10mL volumetric flask, adding dichloromethane to a constant volume of 10mL, and preparing into 1 × 10 - 3 Preparing 2X 10 mol/L mother liquor by taking 200 mu L mother liquor to a 10mL volumetric flask with a pipette -5 And (4) mol/L diluent. 10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 250. Mu.L of a 4X 10 concentrated solution was taken out by a pipette -5 mol/L Compound A dilution and 50. Mu.L of 1X 10 -2 The compound C solution of mol/L is used for a pipetteTaking 250 μ L of 2 × 10 -5 And (3) carrying out ultrasonic treatment on mol/L compound B diluent for 30min, and continuously shaking the diluent during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A to the final acceptor compound B being 2500 -5 mol/L, concentration of Relay acceptor Compound A1X 10 -6 mol/L, final acceptor compound B concentration 5X 10 -7 And (3) measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 83 percent, and the total antenna effect is 48 percent.
Example 14
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 250. Mu.L of a 4X 10-concentrated solution was taken out with a pipette -5 mol/L Compound A solution and 50. Mu.L of 1X 10 -2 The mol/L compound C solution is taken out by a pipette gun, and 100 mu L of the compound C solution with the concentration of 2X 10 is taken - 5 And (3) carrying out ultrasonic treatment on mol/L compound B diluent for 30min, and continuously shaking the diluent during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of the donor compound C to the relay acceptor A to the final acceptor compound B being 2500 - 5 mol/L, concentration of Relay acceptor Compound A1X 10 -6 mol/L, final acceptor compound B concentration 2X 10 -7 And the fluorescence intensity of the sample is measured by a fluorescence spectrophotometer, the energy transfer efficiency is 77 percent, and the total antenna effect is 51.3.
Example 15
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 250. Mu.L of a 4X 10-concentrated solution was taken out with a pipette -5 mol/L Compound A solution and 50. Mu.L of 1X 10 -2 The mol/L compound C solution is taken by a pipette gun, and 50 mu L of the compound C solution with the concentration of 2X 10 is taken -5 And (3) carrying out ultrasonic treatment on mol/L compound B diluent for 30min, and continuously shaking the diluent during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of a donor compound C to a relay acceptor A to a final acceptor compound B being 2500 -5 mol/L, concentration of Relay acceptor Compound A1X 10 -6 mol/L, final acceptor compound B concentration 1X 10 -7 mol/L, measuring the fluorescence intensity of the sample by a fluorescence spectrophotometer, wherein the energy transfer efficiency is 57 percent, and the total antenna efficiency isShould be 55.9.
Example 16
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 250. Mu.L of a 4X 10 concentrated solution was taken out by a pipette -5 mol/L Compound A solution and 50. Mu.L of 1X 10 -2 The mol/L compound C solution is taken out by a pipette gun, and 20 mu L of the compound C solution with the concentration of 2X 10 is taken -5 And (3) carrying out ultrasonic treatment on mol/L compound B diluent for 30min, and continuously shaking the diluent during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of a donor compound C to a relay acceptor A to a final acceptor compound B being 2500 -5 mol/L, concentration of Relay acceptor Compound A1X 10 -6 mol/L, final acceptor compound B concentration 4X 10 -8 And measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 39 percent, and the total antenna effect is 63.1.
Example 17
10mL of CTAB aqueous solution was added to a 10mL Erlenmeyer flask, and 250. Mu.L of a 4X 10 concentrated solution was taken out by a pipette -5 mol/L Compound A solution and 50. Mu.L of 1X 10 -2 The mol/L compound C solution is taken out by a pipette with the concentration of 2X 10 to 10 mu L -5 And (3) carrying out ultrasonic treatment on mol/L compound B diluent for 30min, and continuously shaking the diluent during the ultrasonic treatment to prepare a nanoparticle aqueous solution with the concentration ratio of a donor compound C to a relay acceptor A to a final acceptor compound B being 2500 -5 mol/L, concentration of Relay acceptor Compound A1X 10 -6 mol/L, final acceptor compound B concentration 2X 10 -8 And measuring the fluorescence intensity of the sample by using a fluorescence spectrophotometer, wherein the energy transfer efficiency is 26 percent, and the total antenna effect is 56.2 percent.
Examples 1 to 12 are primary energy transfers and their fluorescence spectra are shown in FIG. 1; examples 13 to 17 are secondary energy transfers and their fluorescence spectra are shown in FIG. 2.
Example 18
The CIE coordinates plot plots the fluorescence of different donor-acceptor ratios, clearly showing that the trend of the fluorescence color is from blue to yellow and then to red, and the trend of the fluorescence color changes across the white emission band, wherein the CIE coordinates of the fluorescence is (0.31,0.33) which is in good agreement with the standard white emission coordinates (0.33) when the donor-acceptor concentration ratio is 1500. Solutions were also visible to the naked eye to exhibit white light emission under 330nm ultraviolet light. From its fluorescence spectrum, it can be seen that its spectral line uniformly covers the entire visible light range, which is a main reason why it can emit white light. The CIE diagram is shown in fig. 3. The white light emission pattern is shown in fig. 4.
Comparative example 1
The emission spectrum peak of the donor compound C and the absorption spectrum peak of the final acceptor compound B overlap by a small amount, and in order to verify whether the donor compound C has energy transferred directly to the final acceptor compound B without passing through the intermediate acceptor compound a, the following studies were performed:
step 2, weighing a certain amount of final acceptor compound B, transferring the final acceptor compound B into a volumetric flask, adding dichloromethane to dissolve the final acceptor compound B, and preparing the final acceptor compound B into a 5 × 10 solution -7 A mol/L solution;
step 3, weighing a certain amount of CTAB, transferring the CTAB into a volumetric flask, and preparing into an aqueous solution with the concentration of 1.0 mmol/L;
and 4, mixing a solution of a trace donor compound C and a trace final acceptor compound B according to a molar ratio of 100.
According to spectrogram data, although a certain energy transfer efficiency exists between the compound C and the compound B, the emission peak of the compound B is extremely low, the fluorescence intensity of a corresponding nanoparticle aqueous solution is reduced sharply, and in contrast, in a system containing the relay acceptor compound A, the emission peak of the final acceptor compound B is very strong, which indicates that the relay acceptor compound A is an indispensable energy transfer bridge and connects the whole secondary energy transfer system in series, so that the key effect is achieved.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent flow transformations made by using the contents of the present specification and the accompanying drawings, or applied directly or indirectly to other related technical fields, are included in the scope of the present invention.
Claims (10)
1. A continuous two-step energy transfer light capture system, the light capture system uses compound C as light collection antenna and energy donor, compound A as relay receptor, compound B as final receptor, under the existence of amphiphilic surfactant, compound C, compound A and compound B and surfactant are micro-emulsified in water solution to form nano particles, and then the light capture system is constructed;
wherein the chemical structures of compounds A, B and C are as follows:
2. the light harvesting system of claim 1, wherein the surfactant is CTAB.
3. A light harvesting system according to claim 1, wherein the molar ratio of compound a to compound C is constant at 50 to 2500, and the molar ratio of compound B to compound C is from 1 to 25.
4. Use of a light harvesting system according to any of claims 1 to 3 in a luminescent material.
5. Use of a light harvesting system according to claim 1 in a white light material.
6. The use according to claim 5, wherein the molar ratio of compound A, compound B and compound C is 6.
7. A method of preparing a light harvesting system according to any of claims 1 to 3, comprising the steps of:
weighing the compound C, the compound A and the compound B, uniformly mixing, adding into a surfactant aqueous solution, and performing ultrasonic treatment to form a uniformly dispersed nanoparticle aqueous solution to obtain a light capture system.
8. The method of claim 7, wherein the concentration of the aqueous surfactant solution is 1.0mmol/L.
9. The method for preparing a light harvesting system according to claim 7, wherein the compound C, the compound A and the compound B are dissolved in a hydrophobic organic solvent and mixed uniformly.
10. The method of claim 9, wherein the hydrophobic organic solvent is selected from one or more of chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110437362.7A CN113136199B (en) | 2021-04-22 | 2021-04-22 | Continuous two-step energy transfer light capture system and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110437362.7A CN113136199B (en) | 2021-04-22 | 2021-04-22 | Continuous two-step energy transfer light capture system and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113136199A CN113136199A (en) | 2021-07-20 |
CN113136199B true CN113136199B (en) | 2023-01-31 |
Family
ID=76813659
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110437362.7A Active CN113136199B (en) | 2021-04-22 | 2021-04-22 | Continuous two-step energy transfer light capture system and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113136199B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113637358B (en) * | 2021-08-05 | 2023-01-31 | 常州大学 | Erasable fluorescent ink and preparation method thereof |
CN113527708B (en) * | 2021-08-11 | 2022-09-27 | 常州大学 | Bridged tetraphenyl vinyl based supramolecular polymer light capture system, preparation and application |
CN114479838B (en) * | 2022-01-20 | 2023-10-31 | 常州大学 | Light capturing system based on column arene and preparation method and application thereof |
CN114835701B (en) * | 2022-03-21 | 2023-07-18 | 华南理工大学 | Photosensitizer with AIE effect and high singlet oxygen yield and preparation method thereof |
CN115926186B (en) * | 2022-12-29 | 2024-04-09 | 常州大学 | Continuous light capturing system based on cyanostyrene supermolecular polymer |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103382388A (en) * | 2013-08-19 | 2013-11-06 | 中国科学院理化技术研究所 | Fluorescent nanoparticle based on quadruple hydrogen bond assembly supermolecules, and preparation method and applications thereof |
CN109206374A (en) * | 2017-07-07 | 2019-01-15 | 香港科技大学 | A kind of tetraphenyl ethylene isomers and its preparation method and application with aggregation-induced emission Yu supermolecule aggregation property |
CN109369543A (en) * | 2018-12-11 | 2019-02-22 | 常州大学 | A kind of tetraphenylethylene synthetic method that urea groups pyrimidone replaces |
CN111303049A (en) * | 2020-02-16 | 2020-06-19 | 常州大学 | Preparation method of water-dispersible fluorescent supramolecular polymer nanospheres |
CN112010869A (en) * | 2020-09-07 | 2020-12-01 | 常州大学 | Light capture system and preparation method and application thereof |
-
2021
- 2021-04-22 CN CN202110437362.7A patent/CN113136199B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103382388A (en) * | 2013-08-19 | 2013-11-06 | 中国科学院理化技术研究所 | Fluorescent nanoparticle based on quadruple hydrogen bond assembly supermolecules, and preparation method and applications thereof |
CN109206374A (en) * | 2017-07-07 | 2019-01-15 | 香港科技大学 | A kind of tetraphenyl ethylene isomers and its preparation method and application with aggregation-induced emission Yu supermolecule aggregation property |
CN109369543A (en) * | 2018-12-11 | 2019-02-22 | 常州大学 | A kind of tetraphenylethylene synthetic method that urea groups pyrimidone replaces |
CN111303049A (en) * | 2020-02-16 | 2020-06-19 | 常州大学 | Preparation method of water-dispersible fluorescent supramolecular polymer nanospheres |
CN112010869A (en) * | 2020-09-07 | 2020-12-01 | 常州大学 | Light capture system and preparation method and application thereof |
Non-Patent Citations (1)
Title |
---|
An efficient artificial light-harvesting system with tunable emission in water constructed from a H-bonded AIE supramolecular polymer and Nile Red;Tangxin Xiao 等;《Chem. Commun.》;20200901;第56卷;12021-12024 * |
Also Published As
Publication number | Publication date |
---|---|
CN113136199A (en) | 2021-07-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113136199B (en) | Continuous two-step energy transfer light capture system and preparation method and application thereof | |
Zhang et al. | Tricolor white-light-emitting carbon dots with multiple-cores@ shell structure for WLED application | |
Xiao et al. | Supramolecular polymer-directed light-harvesting system based on a stepwise energy transfer cascade | |
Xin et al. | Highly stable and luminescent perovskite–polymer composites from a convenient and universal strategy | |
Hu et al. | New multicolored AIE photoluminescent polymers prepared by controlling the pH value | |
Cao et al. | Brighten triplet excitons of carbon nanodots for multicolor phosphorescence films | |
CN112010869B (en) | Light capture system and preparation method and application thereof | |
CN109328402A (en) | Quantum dot light emitting device | |
CN105820585A (en) | Preparation of mesoporous molecular imprinting fluorescent probe and detection of tetracycline antibiotics by mesoporous molecular imprinting fluorescent probe | |
Zhang et al. | Pyrene-based nonwoven fabric with tunable fluorescence properties by employing the aggregation-caused quenching effect | |
CN104926981A (en) | Preparation method for fluorescence sensing material based on molecular imprinting and carbon dots | |
CN108440711B (en) | Water-based naphthalimide fluorescent polymer emulsion and preparation method thereof | |
CN106281307A (en) | A kind of flexible chitosan light-emitting film containing rare earth and preparation method thereof | |
CN107955135A (en) | It is conjugated organic grid nanometer polymer and its methods for making and using same | |
Wang et al. | Stimulus responsive fluorescent hyperbranched polymers and their applications | |
Yang et al. | Copolymer of Fluorene and Triphenylamine Moieties: Direct and Post‐Functionalization Strategy, Structural Characterization, and Chemosensoring Behavior | |
CN114410299B (en) | Carbon dot and preparation method of carbon dot-based composite material | |
Huang et al. | Polymer precursor strategy toward the precise synthesis of uniform hairy carbon dots with tunable sizes and size effects over their fluorescence | |
Soran-Erdem et al. | High-stability, high-efficiency organic monoliths made of oligomer nanoparticles wrapped in organic matrix | |
CN108559064B (en) | Conjugated main chain doped zwitterionic polyfluorene vinylene and preparation and application thereof | |
CN113045978B (en) | Preparation method of carbon quantum dot-water-soluble polyurethane solution | |
CN108358957B (en) | Preparation method of rare earth-polymer nanospheres emitting white light | |
CN104945858A (en) | Preparation method for carboxylic acid type polyfluorene/titanium dioxide nano-hybrid materials | |
CN113527708B (en) | Bridged tetraphenyl vinyl based supramolecular polymer light capture system, preparation and application | |
CN110330963B (en) | Redox-responsive color-changing rare earth supermolecule gel fluorescent material and preparation thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |