A light harvesting system based on continuous energy transfer of pillar aromatics and its preparation method and application

Through a continuous energy transfer light capture system based on column aromatics, nanoparticles are formed by self-assembly of compound G and compound H, and two-step energy transfer is achieved in combination with fluorescent dyes, which solves the problem of insufficient energy transfer steps in the existing system, and realizes high-efficiency energy transfer and preparation of white light emitting materials.

CN115595147BActive Publication Date: 2025-05-06CHANGZHOU UNIV
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Patent Information

Application Number
CN202211234431.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-10-10
Publication Date
2025-05-06
Estimated Expiration
2042-10-10

AI Technical Summary

Technical Problem

The existing artificial light capture systems mainly rely on single-step fluorescence resonance energy transfer, making it difficult to achieve multi-step sequence energy transfer, and the ability to convert solar energy into chemical energy in a water environment is insufficient.

Method used

Using a continuous energy transfer light capture system based on column aromatics, nanoparticles are formed through the host-guest action of compound G and compound H, and a two-step continuous energy transfer system is formed with the fluorescent dye.

Benefits of technology

A wider spectral dimmable photoluminescence is achieved, with a larger Stokes displacement between the energy donor and the final acceptor, with high energy transfer capabilities and ultra-high antenna effects, suitable for the preparation of white light emitting materials and photocatalysts.

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Abstract

The present invention discloses a light-harvesting system based on continuous energy transfer of pillar aromatics, and a preparation method and application thereof. The light-harvesting system uses a tetraphenylethylene compound G modified with a methyl pyridinium salt as a guest and an energy donor, a pillar [5] aromatic compound H modified with an ammonium carboxylate salt as a host, and a fluorescent dye as an energy acceptor. In the present invention, compound G and compound H self-assemble to form nanoparticles through host-guest interaction, and construct a light-harvesting system for continuous energy transfer with the fluorescent dye. The light-harvesting system provided by the present invention has the characteristics of low cost and green environmental protection; the nanoparticle structure is stable; the two-step energy transfer has high-efficiency energy transfer capability and high antenna effect; the luminescent color of the light-harvesting system is adjustable, and can be used to prepare high-efficiency white light emitting devices; and the light-harvesting system can be used for photocatalytic dehalogenation reactions.
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Description

Technical Field

[0001] The invention relates to the technical field of luminescent materials for light-harvesting systems, and in particular to a light-harvesting system based on continuous energy transfer of pillar aromatics, and a preparation method and application thereof. Background Art

[0002] In recent years, solar energy, as an inexhaustible and clean energy source, has attracted more and more attention from the scientific community. In nature, green plants and some photosynthetic bacteria effectively capture, transfer, and store solar energy through photosynthesis, converting light energy into chemical energy. The light harvesting system plays an important role in the photosynthesis process in nature. The light harvesting system is a process in which multiple closely arranged chromophores capture the energy released by the sun and then transfer the captured energy to the receptor. Inspired by photosynthesis, various artificial light harvesting systems (LHS) have been manufactured by mimicking natural photosynthesis in a simplified and modified way, which can be applied to many fields such as optoelectronic device sensing, bioimaging, and information security.

[0003] To date, most artificial light harvesting systems involve fluorescence resonance energy transfer (FRET). FRET is a non-radiative process between an energy donor and an energy acceptor. Specifically, when the emission energy of the donor is absorbed by an appropriate acceptor, the fluorescence of the acceptor can be excited by the non-radiative energy transfer from the donor to the acceptor. To achieve FRET, three basic factors should be considered when selecting the donor and the acceptor: first, the absorption band of the acceptor should largely overlap with the fluorescence emission band of the donor; second, the distance between the donor and the acceptor should be much larger than their collision diameter, but not too far from each other; and finally, the donor and the acceptor must be arranged in an appropriate manner. However, to date, almost all artificial light harvesting systems focus on a one-step conventional energy transfer from the donor to the acceptor involving two chromophores. Compared with the one-step energy transfer, the two-step energy transfer can still achieve a wider spectrum tunable photoluminescence, and the Stokes shift between the energy donor and the final acceptor is also larger, even when there is no spectral overlap between the energy donor and the final acceptor. Therefore, designing efficient artificial light-harvesting systems with sequential energy transfer via supramolecular assembly remains a challenge, and it is of great significance to establish a multi-step sequential FRET system capable of converting solar energy into chemical energy in an aqueous environment. Summary of the invention

[0004] In view of the above technical problems, the present invention provides a light harvesting system based on continuous energy transfer of pillar aromatics, and a preparation method and application thereof.

[0005] To achieve the above object, the technical solution adopted by the present invention is:

[0006] On the one hand, the present invention provides a light harvesting system based on continuous energy transfer of pillararenes, wherein the light harvesting system uses compound G as a guest and energy donor, compound H as a host, and a fluorescent dye as an energy acceptor;

[0007] Wherein, the chemical structure of compound G is shown in formula (I):

[0008]

[0009] The chemical structure of compound H is shown in formula (II):

[0010]

[0011] As a preferred embodiment, the energy acceptor includes an intermediate acceptor A and a final acceptor B;

[0012] Preferably, the intermediate receptor A is Eosin Y; the chemical structure of Eosin Y is shown in formula (III):

[0013]

[0014] Preferably, the final receptor B is Nile Red; the chemical structure of Nile Red is shown in formula (IV):

[0015]

[0016] In the technical solution of the present invention, the compound G and the compound H self-assemble to form nanoparticles through host-guest interaction, and form the light-harvesting system with the fluorescent dye;

[0017] Preferably, the concentration ratio of the compound G to the compound H is 1-50:1, more preferably 4:1.

[0018] As a preferred embodiment, in the light harvesting system, the molar concentration ratio of compound G to intermediate acceptor A is 100 to 1000:1, for example, 100:1, 150:1, 200:1, 300:1, 400:1, 500:1, 700:1, 900:1, 1000:1 or any ratio therebetween;

[0019] Preferably, in the light harvesting system, the molar concentration ratio of the intermediate acceptor A to the compound G is 1000:10.

[0020] As a preferred embodiment, in the light harvesting system, the final molar concentration ratio of the receptor B to the compound G is 1 to 4:1000, such as 1:1000, 2:1000, 3:1000, 4:1000 or any ratio therebetween.

[0021] In certain specific embodiments, the concentration of compound G in the light harvesting system can be 1×10 -5 ~1×10 -4 mol / L, the concentration of compound H can be 2×10 -6 ~1×10 -5 mol / L, the concentration of compound A can be 5×10 -8 ~5×10 -7 mol / L, the concentration of compound B can be 4×10 -8 ~8×10 -8 mol / L.

[0022] In another aspect, the present invention provides a method for preparing the above light capture system, comprising the following steps:

[0023] Step 1: dissolving compound G and compound H in an aqueous solution and self-assembling to form a nanoparticle solution;

[0024] Step 2: adding a solution containing fluorescent dye A to the solution of step 1, and obtaining a light harvesting system for primary energy transfer after dispersion;

[0025] Step 3: Add the solution containing fluorescent dye B into the solution of step 2, and obtain the light harvesting system after dispersion.

[0026] As a preferred embodiment, the solvent of the solution containing the fluorescent dye A is selected from at least one of dimethyl sulfoxide and water;

[0027] Preferably, the solvent of the solution containing the fluorescent dye B is selected from at least one of dimethyl sulfoxide and water.

[0028] As a preferred embodiment, in step 1, the self-assembly is performed under ultrasonic conditions;

[0029] Preferably, in step 2, the dispersing is performed under ultrasonic conditions;

[0030] Preferably, in step 3, the dispersing is performed under ultrasonic conditions.

[0031] In yet another aspect, the present invention provides use of the above light harvesting system in preparing luminescent materials.

[0032] Preferably, the luminescent material is a photoluminescent material with an excitation wavelength of 300-400 nm.

[0033] Preferably, the luminescent material is a color-adjustable luminescent material.

[0034] In yet another aspect, the present invention provides use of the above light harvesting system in preparing white light emitting materials.

[0035] Preferably, the molar concentration ratio of the compound G, the intermediate receptor A, and the final receptor B is 1000:10:4;

[0036] Preferably, the excitation wavelength is 325 nm;

[0037] Preferably, the invention is used in the preparation of white light LED lamps.

[0038] In another aspect, the present invention provides the use of the above light harvesting system as a photocatalyst;

[0039] Preferably, use as a photocatalyst in a dehalogenation reaction;

[0040] Preferably, the use as a photocatalyst in the dehalogenation reaction of α-bromoacetophenone:

[0041] Preferably, the use as a photocatalyst in the dehalogenation reaction shown in formula (V);

[0042]

[0043] The above technical solution has the following advantages or beneficial effects:

[0044] The present invention provides a light-harvesting system, which uses a tetraphenylethylene compound G modified with a methylpyridinium salt as a guest and an energy donor, a columnar[5]arene compound H modified with an ammonium carboxylate salt as a host, and a fluorescent dye as an energy acceptor. In the present invention, the compound G and the compound H are self-assembled to form nanoparticles through the host-guest interaction, and then the fluorescent dye is added to construct a continuous energy transfer light-harvesting system.

[0045] The light capture system of the present invention has the following advantages:

[0046] (1) The light harvesting system provided by the present invention has a two-step continuous energy transfer process, which can better simulate the energy transfer path of photosynthesis in nature;

[0047] (2) The light-harvesting system provided by the present invention can still transfer energy well under very high donor-acceptor ratio conditions. A unit acceptor can receive energy transferred by hundreds or even thousands of times the amount of donors. It also has the advantages of high energy transfer capability and ultra-high antenna effect. The highest energy transfer efficiency of the first step of energy transfer (compound G to intermediate acceptor A) is 79%, and the best antenna effect is 36.7%. The highest energy transfer efficiency of the second step of energy transfer (intermediate acceptor A to final acceptor B) is 79.6%, and the best antenna effect is 7.8%.

[0048] (3) The luminescent color of the light-harvesting system provided by the present invention is adjustable, and its fluorescence variation trend just includes the white light emission band, so white light emitting materials can be prepared and applied to white light LED lamps;

[0049] (4) The light harvesting system provided by the present invention can also be used as a photocatalyst in dehalogenation reactions, which can significantly increase the reaction rate;

[0050] (5) The light-harvesting system provided by the present invention is that compound G and compound H are self-assembled into nanoparticles through host-guest interaction and are uniformly dispersed in an aqueous solution, which has the effects of low cost and green environmental protection; and the structure is stable and can be stored for a long time. BRIEF DESCRIPTION OF THE DRAWINGS

[0051] Figure 1 1 and 2 are fluorescence spectra of different ratios of guest compound G and host compound H in Example 1.

[0052] Figure 2 : The fluorescence spectra of the donor compound G and the intermediate acceptor A in different ratios in Example 2 in aqueous solution.

[0053] Figure 3 1 is the fluorescence spectra of the donor compound G, the intermediate acceptor compound A and the final acceptor compound B in different proportions in Example 2 in aqueous solution.

[0054] Figure 4 This is the CIE 1931 color coordinate diagram at different receptor contents in Example 2.

[0055] Figure 5 This is the white light emission fluorescence spectrum when the concentration ratio of donor compound G, intermediate acceptor A, and final acceptor B in Example 3 is 10000:10:4.

[0056] Figure 6 Schematic diagram of the process of preparing a white light LED lamp using a light capture system in Example 3.

[0057] Figure 7 is the hydrogen nuclear magnetic resonance spectrum of compound G prepared in Preparation Example 1.

[0058] Figure 8 is the carbon NMR spectrum of compound G prepared in Preparation Example 1.

[0059] Fig. 9 This is the high-resolution mass spectrum of compound G prepared in Preparation Example 1. DETAILED DESCRIPTION

[0060] The following embodiments are only some embodiments of the present invention, rather than all embodiments. Therefore, the detailed description in the embodiments of the present invention provided below is not intended to limit the scope of the present invention claimed for protection, but merely represents selected embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making creative work belong to the protection scope of the present invention.

[0061] In the present invention, unless otherwise specified, all equipment and raw materials can be purchased from the market or are commonly used in the industry. The methods in the following embodiments are all conventional methods in the art unless otherwise specified.

[0062] Preparation Example 1 Preparation of Compound G:

[0063] In this preparation example, compound G is synthesized from compound 1 as a raw material, and the structural formula of compound 1 is shown below:

[0064]

[0065] It was prepared according to the method in Angew.Chem.Int.Ed.2020,59,12800–12805.

[0066] The preparation process of compound G is as follows: In a 100 mL three-necked flask, compound 1 (1.00 g, 1.8 mmol) and p-methylpyridine (2.46 g, 26.4 mmol) were dissolved in acetone (30 mL). 2 The mixture was heated to reflux under atmosphere for 24 h. Post-treatment: After the reaction mixture was cooled to room temperature, it was rotary evaporated and the crude product was purified by silica gel column (methanol: water = 1:1, V / V) to obtain a yellow hard cream solid, which was compound G (0.94 g, 79%).

[0067] The H NMR spectrum of compound G is as follows Figure 7 As shown: 1 H NMR (300 MHz, DMSO-d 6 ,298K): δ (ppm) = 8.97 (d, J = 6.0Hz, 2H, Py-H), 8.00 (d, J = 6.0Hz, 2H, Py-H), 7.15-7.07 (m, 9H, Ar-H), 6.9 9-6.92(m,6H,Ar-H),6.84(d,J=9.0Hz,2H,Ar-H),6.67(d,J=9.0Hz,2H,Ar-H),4.54(t,J=6.0Hz,2H,-CH 2 ),3.85(t,J=6.0Hz,2H,-CH 2 ),2.61(s,3H,-CH 3 ),1.92-1.83(m,2H,-CH 2 ),1.67-1.58(m,2H,-CH 2 ),1.25(br,12H,-CH 2 ).

[0068] The NMR carbon spectrum of compound G is as follows Figure 8 As shown: 13C NMR (75 MHz, DMSO-d 6 ,298K): δ(ppm)=159.2,157.8,144.2,144.0,143.9,140.7,140.1,135.7,132.4,131.2,131.1,128 .8,128.4,128.3,126.9,126.9,114.1,79.7,67.7,60.3,31.1,29.3,29.2,28.8,26.0,25.8,21.8.

[0069] The high-resolution mass spectrum of compound G is as follows Fig. 9 Shown: HR-ESI-MS: m / z[M-Br] + Calculate for [C 42 H 46 NO] + =580.3574, found 580.3567.

[0070] According to the above experimental characterization, the structure of compound G is determined as follows:

[0071]

[0072] Example 1 Preparation of supramolecular nanoparticles:

[0073] In this example, compound H was synthesized according to the literature J. Mater. Chem. B, 2016, 4, 2819-2827, and its structure is as follows:

[0074]

[0075] Preparation of supramolecular nanoparticles:

[0076] Step 1, weigh 19.8 mg of the compound G prepared in Preparation Example 1 into a 5 mL volumetric flask, add deionized water to make up to 5 mL, and prepare a 6 mmol / L mother solution;

[0077] Step 2, weigh 10.4 mg of compound H into a 10 mL volumetric flask, add deionized water to make up to 10 mL, and prepare a 0.5 mmol / L mother solution;

[0078] Step 3: Use a pipette to transfer appropriate amounts of the mother solution of compound G and the mother solution of compound H to a 5 mL volumetric flask and mix them evenly. Then add deionized water to the volume and ultrasonicate for 3 minutes to form nanoparticles dispersed in water.

[0079] Fluorescence titration experiment with different host-guest ratios:

[0080] At 25°C, the concentration of the aqueous solution of the guest compound G was fixed at 20 μM, and different equivalents of the host compound H (0.5-40 μM) were added thereto to measure its optical transmittance. According to the change of the optical transmittance at 450 nm, a concentration-transmittance line graph was obtained. The lowest point corresponds to a concentration of 5 μM H, that is, the optimal ratio of compound G to compound H is 4:1, where the concentration of compound G is 2×10 -5 mol / L, the concentration of compound H is 5×10 -6 mol / L.

[0081] In this embodiment, the excitation was measured at 325 nm. The fluorescence spectrum of Figure 1 shown.

[0082] In this embodiment, the ultrasonic instrument used is an ultrasonic cleaning machine commonly used in laboratories, and the frequency is 40 kHz.

[0083] Example 2 Preparation of light harvesting system:

[0084] In this embodiment, compound G is used as an energy donor, fluorescent dye A eosin Y is used as an intermediate acceptor, and fluorescent dye B Nile red is used as a final acceptor. The preparation method is as follows:

[0085] Step 1, weigh 19.8 mg of the compound G prepared in Preparation Example 1 into a 5 mL volumetric flask, add deionized water to make up to 5 mL, and prepare a 6 mmol / L mother solution;

[0086] Step 2, weigh 10.4 mg of compound H into a 10 mL volumetric flask, add deionized water to make up to 10 mL, and prepare a 0.5 mmol / L mother solution;

[0087] Step 3, weigh 16.20 mg of fluorescent dye A into a 5 mL volumetric flask, add dimethyl sulfoxide to make up to 5 mL, and prepare a 5 mmol / L mother solution;

[0088] Step 4, weigh 1.6 mg of fluorescent dye B into a 5 mL volumetric flask, add dimethyl sulfoxide to make up to 5 mL, and prepare a 1 mmol / L mother solution;

[0089] Step 5: Use a pipette to transfer appropriate amounts of the mother solution of compound G, the mother solution of compound H, and the mother solution of fluorescent dye A Eosin Y into a 5 mL volumetric flask, mix well, then add deionized water to make up the volume, and form nanoparticles after ultrasonication for 3 minutes. Aqueous solution; wherein the nanoparticles The concentrations of compound G, compound H, and compound A in the aqueous solution are shown in Table 1 ;

[0090] Table 1

[0091]

[0092] Step 6: Use a pipette to transfer appropriate amounts of The aqueous solution and the mother solution of fluorescent dye B were mixed in a 5 mL volumetric flask, and then deionized water was added to the volume. After ultrasonic treatment for 3 minutes, nanoparticles dispersed in water were formed. Among them, nanoparticles dispersed in water In the above, the concentrations of compound G, compound H, compound A, and compound B are shown in Table 2 ;

[0093] Table 2

[0094]

[0095] In this embodiment, the prepared samples were measured under 325 nm excitation. Nanoparticles, Fluorescence spectrum of nanoparticles. Figure 2 This embodiment is shown Fluorescence spectra of nanoparticles with different ratios of donor compound G and intermediate acceptor A in aqueous solution, Figure 3 This embodiment is shown Fluorescence spectra of nanoparticles with different ratios of donor compound G, intermediate acceptor compound A and final acceptor compound B in aqueous solution.

[0096] In this embodiment, the energy transfer efficiency and antenna effect of the nanoparticles are characterized by the fluorescence spectrum obtained through the above test, and the process is as follows:

[0097] According to the measured Nanoparticles and The fluorescence spectrum of the nanoparticles was used to calculate the first step energy transfer efficiency (Φ ET ):

[0098] Φ ET =1-I DA / I D (eq.S1)

[0099] Among them, I DA and I D They are (donor and acceptor) and The fluorescence intensity of (donor) at 480nm when excited at 325nm. Substituting the measured data into formula S1, the maximum energy transfer efficiency of the first step of energy transfer (compound G to compound A) is 79%. At this time, [H] = 5×10 -6 mol / L,[G]=2×10 -5 mol / L,[A]=2×10 -7 mol / L.

[0100] According to the measured Nanoparticles and The fluorescence spectrum of the nanoparticles was used to calculate the energy transfer efficiency (Φ ET ):

[0101] Φ ET =1-I DA / I D (eq.S1)

[0102] Among them I DA and I D They are (donor and acceptor) and The fluorescence intensity of the donor at 550 nm when excited at 325 nm. The maximum energy transfer efficiency of the second step energy transfer (compound A to compound B) measured according to equation S1 reached 79.6%. At this time, [H] = 5 × 10 -6 mol / L,[G]=2×10 -5 mol / L,[A]=2×10 - 7 mol / L,[B]=8×10 -8 mol / L.

[0103] According to the measured Nanoparticles and The fluorescence spectrum of the nanoparticles was used to calculate the antenna effect (AE) of the first step of energy transfer using Equation S2:

[0104] AE=I' DA,325 / I DA,480 =(I DA,325 -I D,325 ) / I DA,480 (eq.S2)

[0105] Among them I DA,325 and I DA,480 They are Fluorescence intensity at 550nm under excitation at 325nm and 480nm. D,325 for The emission spectrum was normalized at 480 nm and the fluorescence intensity at 550 nm under 325 nm excitation. According to equation S2, the antenna effect of the first step of energy transfer (compound G to compound A) is up to 36.7%. At this time, [H] = 5 × 10 - 6 mol / L,[G]=2×10 -5 mol / L,[A]=4×10 -8mol / L.

[0106] According to the measured Nanoparticles and The fluorescence spectrum of the nanoparticles was used to calculate the antenna effect (AE) of the second step energy transfer using Equation S2:

[0107] AE=I' DA,325 / I DA,550 =(I DA,325 -I D,325 ) / I DA,550 (eq.S2)

[0108] Among them, I DA,325 and I DA,550 They are Fluorescence intensity at 625nm under excitation at 325nm and 550nm. D,325 for The emission spectrum was normalized at 550 nm and the fluorescence intensity at 625 nm under 325 nm excitation. According to equation S2, the antenna effect of the second step energy transfer (compound A to compound B) is up to 7.8%. At this time, [H] = 5 × 10 -6 mol / L,[G]=2×10 -5 mol / L,[A]=2×10 -7 mol / L,[B]=8×10 -8 mol / L.

[0109] This embodiment will The fluorescence spectrum is converted into CIE color coordinates, such as Figure 4 As shown:

[0110] The CIE1931 color coordinates can reflect the color change process of the fluorescent light capture system. In the CIE1931 coordinate diagram, the x-axis represents the red part, the y-axis represents the green part, and the z-axis represents the blue part. After the fluorescence emission data of the fluorescent light capture system is processed by the CIE1931 software, a continuous coordinate point can be obtained. From the CIE1931 coordinate diagram, it can be clearly seen that with the addition of receptor A, the color changes from blue fluorescence to green fluorescence. After the continuous addition of receptor B, the color changes from green fluorescence to red fluorescence, which reflects the change trend of the fluorescence color of the light capture system. By adjusting the light capture system Different proportions of A and B can produce a white light emitting system, whose white light emission spectrum is reflected in the coordinates of (0.32, 0.33) in CIE1931, which is close to the coordinates of pure white light emission (0.33, 0.33).

[0111] Example 3 Light capture system for preparing white light LED lamp:

[0112] In this embodiment, a white light LED lamp is prepared using the light capture system obtained in the above method, wherein the nanoparticles Middle: [H] = 5 × 10 -6 mol / L, [G] = 2 × 10 -5 mol / L, [A] = 2 × 10 -8 mol / L, [B] = 8 × 10 -9 mol / L; the concentration ratio of donor compound G, intermediate acceptor A, and final acceptor B is 10000:10:4. The white light emission fluorescence spectrum at this concentration ratio is shown in Figure 5 Therefore, the nanoparticles prepared in this embodiment can be further applied to the production of white LED lamps.

[0113] The preparation process of white light LED lamp is shown in Figure 6 , the specific steps are as follows:

[0114] The light-harvesting system solution with the above ratio was repeatedly coated on a blue LED bulb (365nm), which produced bright white light after applying a bias of 3V.

[0115] Example 4 Light harvesting system for photocatalytic dehalogenation reaction:

[0116] In this embodiment, The system acts as a photocatalyst to catalyze the dehalogenation reaction of α-bromoacetophenone in aqueous solution.

[0117]

[0118] Here are the steps:

[0119] α-Bromoacetophenone (0.1 mmol, 20.0 mg), diethyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (0.1 mmol, 27.9 mg) and N,N-diisopropylethylamine (DIPEA) (0.2 mmol, 25.8 mg) were dissolved in a quartz Schlenk tube. The mixture was cooled with liquid nitrogen, evacuated, and circulated with nitrogen for three times. Then, the mixture was stirred at room temperature and illuminated with a xenon lamp (100 mW / cm 2 ) was irradiated for 8 h and diluted with ether (12 × 2 mL). The organic layers were collected and 2 SO 4 The solvent was removed in vacuo and the product was purified by silica gel column chromatography (PE:DCM=30:1) to obtain a yellow liquid (0.1 mmol, 11.8 mg) with a yield of 98% (Entry 4).

[0120] As shown in Table 3, no catalyst is used (Entry 1), or (Entry 2), A+B (Entry 3) as catalyst, or without light (Entry 5), the yield is not ideal.

[0121] Table 3

[0122]

[0123] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. A light harvesting system based on continuous energy transfer of pillararenes, characterized in that: The light harvesting system uses compound G as the guest and energy donor, compound H as the host, and a fluorescent dye as the energy acceptor; Wherein, the chemical structure of compound G is shown in formula (I): The chemical structure of compound H is shown in formula (II): The energy acceptor includes an intermediate acceptor A and a final acceptor B; The intermediate receptor A is Eosin Y; the chemical structure of Eosin Y is shown in formula (III): The final receptor B is Nile Red; the chemical structure of Nile Red is shown in formula (IV):

2. The light capture system according to claim 1, characterized in that The compound G and the compound H are self-assembled to form nanoparticles through host-guest interaction, and form the light harvesting system with the fluorescent dye.

3. The light capture system according to claim 1, characterized in that The concentration ratio of the compound G to the compound H is 1 to 50:

1.

4. The light capture system according to claim 1, characterized in that The concentration ratio of compound G to compound H is 4:

1.

5. The light capture system according to claim 1, characterized in that In the light harvesting system, the molar concentration ratio of compound G to intermediate acceptor A is 100-1000:

1.

6. The light capture system according to claim 1, characterized in that In the light harvesting system, the molar concentration ratio of the intermediate acceptor A to the compound G is 1000:

10.

7. The light capture system according to claim 1, characterized in that In the light harvesting system, the final molar concentration ratio of the receptor B to the compound G is 1 to 4:1000.

8. The method for preparing the light harvesting system according to any one of claims 1 to 7, characterized in that: The steps include: Step 1: dissolving compound G and compound H in an aqueous solution and self-assembling to form a nanoparticle solution; Step 2: adding a solution containing fluorescent dye A to the solution of step 1, and obtaining a light harvesting system for primary energy transfer after dispersion; Step 3: Add the solution containing fluorescent dye B into the solution of step 2, and obtain the light harvesting system after dispersion.

9. The preparation method according to claim 8, characterized in that: The solvent of the solution containing the fluorescent dye A is selected from at least one of dimethyl sulfoxide and water.

10. The preparation method according to claim 8, characterized in that: The solvent of the solution containing the fluorescent dye B is selected from at least one of dimethyl sulfoxide and water.

11. The preparation method according to claim 8, characterized in that: In step 1, the self-assembly is performed under ultrasonic conditions.

12. The preparation method according to claim 8, characterized in that: In step 2, the dispersion is carried out under ultrasonic conditions.

13. The preparation method according to claim 8, characterized in that: In step 3, the dispersion is carried out under ultrasonic conditions.

14. Use of the light harvesting system according to any one of claims 1 to 7 in the preparation of luminescent materials.

15. The use according to claim 14, characterized in that: The luminescent material is a photoluminescent material, and the excitation wavelength is 300-400nm.

16. The use according to claim 14, characterized in that The luminescent material is a color-adjustable luminescent material.

17. Use of the light harvesting system according to any one of claims 1 to 7 in preparing white light emitting materials.

18. The use according to claim 17, characterized in that The molar concentration ratio of the compound G, the intermediate receptor A, and the final receptor B is 1000:10:

4.

19. The use according to claim 17, characterized in that: The excitation wavelength is 325 nm.

20. The use according to claim 17, characterized in that Application in the preparation of white light LED lamps.

21. Use of the light harvesting system according to any one of claims 1 to 7 as a photocatalyst.

22. The use according to claim 21, characterized in that Application as a photocatalyst in dehalogenation reactions.

23. The use according to claim 22, characterized in that Application as a photocatalyst in the dehalogenation reaction of α-bromoacetophenone.

24. The use according to claim 23, characterized in that Application as a photocatalyst in the dehalogenation reaction shown in formula (V);

Citation Information

Patent Citations

  • Light capture system based on pillararene as well as preparation method and application of light capture system

    CN114479838A