Circularly polarized luminescent tunable aryl acetylene supramolecular polymer, preparation and application
By forming arylacetylene supramolecular polymers through non-covalent interactions and utilizing fluorine atom modification and stacking mode modulation, the problem of controlling the wavelength of circularly polarized emission in existing technologies has been solved, achieving tunable circularly polarized emission in the range of 378-450nm, which is suitable for optical devices and information encryption fields.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- UNIV OF SCI & TECH OF CHINA
- Filing Date
- 2026-02-13
- Publication Date
- 2026-05-12
AI Technical Summary
Existing technologies for controlling the wavelength of circularly polarized light emission involve cumbersome chemical modification steps that are difficult to precisely control, and the supramolecular assemblies lack stability, making it difficult to meet the application requirements of optical devices and information encryption fields.
Arylacetylene supramolecular polymers are formed through non-covalent interactions. The electronic structure of the chromophore is changed by modifying it with fluorine atoms. The stacking mode is controlled by rapid cooling and stirring or sonication, thus achieving tunable wavelength of circularly polarized emission.
It achieves tunable circularly polarized emission wavelength in the 378-450nm band, has a high efficiency emission asymmetry factor, and the polymer system has simple processing and controllable cost, showing good application prospects.
Smart Images
Figure CN121718034B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of circularly polarized luminescent materials technology, and particularly to arylaceyne supramolecular polymers with tunable circularly polarized luminescence, their preparation, and applications. Background Technology
[0002] Adjusting the wavelength of circularly polarized emission (CPL) is crucial for expanding its applications in optical devices and information encryption. Constructing CPL-active materials based on π-conjugated aromatic chromophores is a common strategy for achieving efficient luminescence. Currently, there are two main approaches to controlling the wavelength of CPL: one is to introduce specific functional groups into the chromophore through chemical modification, thereby altering its electronic structure and energy level distribution; the other is to utilize supramolecular interactions to control the molecular packing pattern, thus affecting the excited-state properties. However, the former often involves cumbersome synthesis steps and is difficult to precisely control luminescence performance, while the latter is sensitive to external conditions and the stability of the assembled structure is often insufficient; both have certain limitations. Summary of the Invention
[0003] Based on the technical problems existing in the background technology, this invention proposes a circularly polarized luminescence tunable arylaceyne supramolecular polymer, its preparation and application, and develops CPL materials with tunable properties.
[0004] This invention proposes a supramolecular polymer of arylacetylene with tunable circularly polarized luminescence. This polymer is formed by dissolving arylacetylene in an organic solvent through non-covalent interactions. The structural formula of the arylacetylene is as follows:
[0005]
[0006] In the formula, R1-R4 are all one of F, H and OCH3.
[0007] Preferably, the solvent is methylcyclohexane and / or cyclohexane.
[0008] Preferably, the concentration of arylaceyne in the organic solvent is 0.1-1 mM.
[0009] This invention proposes a method for preparing an arylacetylene supramolecular polymer with tunable circularly polarized luminescence. The arylacetylene supramolecular polymer is as described above, and the method steps are as follows:
[0010] S1: Methyl gallate and bromododecane are added to DMF and reacted to obtain compound A;
[0011] S2: Compound A and sodium hydroxide are added to ethanol and reacted to give compound B;
[0012] S3: Compound B, 1-(4-bromophenyl)ethylamine, 1-ethyl-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine were added to dichloromethane to react and prepare the first intermediate;
[0013] S4: The first intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide and trimethylsilylacetylene are reacted with triethylamine under an inert atmosphere to obtain the second intermediate;
[0014] S5: Arylacetylene is prepared by reacting a second intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide, and diiodine-substituted aromatic compounds with triethylamine under an inert atmosphere.
[0015] S6: Dissolve arylaceyne in an organic solvent to obtain a arylaceyne supramolecular polymer with tunable circularly polarized luminescence.
[0016] Preferably, the molar ratio of methyl gallate to dodecane bromo in S1 is 1:4-8;
[0017] And / or, the reaction temperature in S1 is 70-90℃, and the reaction time is 10-14 hours.
[0018] Preferably, the molar ratio of compound A to sodium hydroxide in S2 is 1:6-10;
[0019] And / or, the reaction temperature in S2 is 20-30℃, and the reaction time is 8-16 hours.
[0020] Preferably, the molar ratio of compound B, 1-(4-bromophenyl)ethylamine, 1-ethyl-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine in S3 is 1:1-1.2:2.2-2.6:1.5-2;
[0021] And / or, the reaction temperature in S3 is 25-35℃, and the reaction time is 10-18 hours.
[0022] Preferably, the molar ratio of the first intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide and trimethylsilylacetylene in S4 is 1:0.05-0.15:0.05-0.15:4-8;
[0023] And / or, the reaction temperature in S4 is 75-85℃, and the reaction time is 12-16 hours.
[0024] Preferably, the molar ratio of the second intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide, and diiodosubstituted aromatic compound in S5 is 1:0.005-0.02:0.01-0.03:0.5-0.55;
[0025] And / or, the reaction temperature in S5 is 75-85℃, and the reaction time is 12-18 hours.
[0026] Preferably, the diiodine-substituted aromatic compound in S5 is one of diiodobenzene, 1,4-diiodotetrafluorobenzene, and 1,4-diiodo-2,5-dimethyl ether.
[0027] This invention proposes the application of a circularly polarized luminescent arylaceyne supramolecular polymer in circularly polarized luminescent materials, wherein the arylaceyne supramolecular polymer is as described above.
[0028] Beneficial technical effects of the present invention:
[0029] (1) This invention provides a novel circularly polarized luminescent supramolecular polymer material and its preparation method. Through non-covalent interactions, a supramolecular polymer system with efficient circularly polarized luminescence characteristics is successfully constructed. This strategy is not only simple in process and controllable in cost, but also has good prospects for practical application.
[0030] (2) This invention employs two methods to construct supramolecular polymer materials with different circularly polarized wavelengths. The first method involves introducing fluorine atoms and methoxy groups to modify the chromophores, altering their electronic structure and thus changing the circularly polarized emission wavelength. The second method involves compounds of structural formulas 1-4 exhibiting both parallel and slip-stacking modes during assembly. When rapidly cooled from high temperature to room temperature, the resulting supramolecular polymer forms a parallel stacking mode (belonging to metastable polymers), exhibiting one type of circularly polarized emission wavelength. Stirring or sonication transforms this stacking mode into a slip-stacking mode (belonging to stable polymers), resulting in another type of circularly polarized emission wavelength. These two methods achieve tunable circularly polarized emission wavelengths within the 378-450 nm band and demonstrate a high emission asymmetry factor. Attached Figure Description
[0031] Figure 1 The supramolecular assembly energy field diagram prepared in Example 3 of this invention;
[0032] Figure 2 The analytical spectrum of the luminescent material prepared in Example 1 of this invention is shown; wherein (A) is 1 H NMR, (B) is mass spectrometry;
[0033] Figure 3 The analytical spectrum of the luminescent material prepared in Example 2 of this invention is shown; wherein (A) is 1 H NMR, (B) is mass spectrometry;
[0034] Figure 4 The analytical spectrum of the luminescent material prepared in Example 3 of this invention is shown; wherein (A) is 1 H NMR, (B) is mass spectrometry;
[0035] Figure 5 The analytical spectrum of the luminescent material prepared in Example 4 of this invention is shown; wherein (A) is 1 H NMR, (B) is mass spectrometry;
[0036] Figure 6 The analytical spectrum of the luminescent material prepared in Example 5 of this invention is shown; wherein (A) is 1 H NMR, (B) is mass spectrometry;
[0037] Figure 7 The analytical spectrum of the luminescent material prepared in Example 6 of this invention is shown; wherein (A) is 1 H NMR, (B) is mass spectrometry;
[0038] Figure 8 The images are transmission electron microscope images of the luminescent materials prepared in Example 1 at different magnifications according to the present invention; where (A) is 200 nm and (B) is 500 nm.
[0039] Figure 9 The circular dichroism spectra of the luminescent materials prepared in Examples 1 (solid line) and 2 (dashed line) of this invention are shown.
[0040] Figure 10 The image shows the spectrum of the luminescent material prepared in Example 1 of this invention; where (A) is the fluorescence spectrum and (B) is the circularly polarized fluorescence spectrum.
[0041] Figure 11 The images show transmission electron microscope (TEM) images of the luminescent materials prepared in Example 3 at different magnifications according to the present invention; where (A) is 200 nm and (B) is 0.5 μm.
[0042] Figure 12 The circular dichroism spectra of the luminescent materials prepared in Examples 3 (solid line) and 4 (dashed line) of this invention are shown.
[0043] Figure 13 The image shows the spectrum of the luminescent material prepared in Example 1 of this invention; where (A) is the fluorescence spectrum and (B) is the circularly polarized fluorescence spectrum.
[0044] Figure 14 This is a transmission electron microscope image of the luminescent material prepared in Example 5 of the present invention;
[0045] Figure 15 The circular dichroism spectra of the luminescent materials prepared in Examples 5 (solid line) and 6 (dashed line) of this invention are shown.
[0046] Figure 16The images show the spectra of the luminescent materials prepared in Examples 5 (solid line) and 6 (dashed line) of this invention; where (A) is the fluorescence spectrum and (B) is the circularly polarized fluorescence spectrum. Detailed Implementation
[0047] The present invention will be further explained below with reference to specific embodiments.
[0048] The synthetic route of the circularly polarized luminescence-tunable arylaceyne supramolecular polymer of the present invention is as follows:
[0049]
[0050] Example 1
[0051] Methyl gallate (1.8 g, 10 mmol) and bromododecane (13.2 g, 60 mmol) were added to N,N-dimethylformamide (60 mL) and stirred overnight at 80 °C. After cooling the reaction mixture to room temperature, the solvent was removed by rotary evaporation. The mixture was extracted with dichloromethane and water, and the organic phase was dried over anhydrous sodium sulfate and concentrated. The reactants were purified by silica gel column chromatography (petroleum ether / chloroform = 10:1, v / v) to give a white solid product, denoted as compound A.
[0052] Compound A (3.4 g, 5 mmol) and sodium hydroxide (1.6 g, 40 mmol) were added to ethanol (60 mL) and stirred overnight at room temperature. The mother liquor was gradually added to hydrochloric acid aqueous solution (pH = 1) (500 mL) to obtain a white solid. The white solid was purified by silica gel column chromatography (petroleum ether / chloroform = 10:1, v / v) to obtain a white solid product, denoted as compound B.
[0053] Compound B (10 g, 14.8 mmol), (S)-(+)-1-(4-bromophenyl)ethylamine (3.2 g, 16.2 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide (6.8 g, 35.6 mmol), and 4-dimethylaminopyridine (25.2 g, 25.2 mmol) were added to 100 mL of dichloromethane and reacted overnight with magnetic stirring. The solvent was then evaporated, and the mixture was extracted with water and dichloromethane. The dichloromethane was dried over anhydrous magnesium sulfate, and the sample was mixed with silica gel powder. The mixture was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 10:1, v / v) to give a white solid product, designated as the first intermediate.
[0054] Dichlorobis(triphenylphosphine)palladium (484 mg, 0.68 mmol), copper iodide (132 mg, 0.68 mmol), the first intermediate (6 g, 6.8 mmol), and trimethylsilylacetylene (4.4 g, 41.2 mmol) were added to triethylamine (Et3N, 60 mL) under a nitrogen atmosphere and reacted overnight at 85 °C with magnetic stirring. The reaction mixture was cooled to room temperature, the solvent was then evaporated, and water and dichloromethane were added for extraction. The dichloromethane was then dried over anhydrous magnesium sulfate, and silica gel powder was added and the mixture was stirred. The sample was then purified by silica gel column chromatography (petroleum oil ether / dichloromethane = 1:1, v / v) to give a white solid, designated as the second intermediate.
[0055] Dichlorobis(triphenylphosphine)palladium (20 mg, 0.03 mmol), copper iodide (5 mg, 0.03 mmol), a second intermediate (1080 mg, 1.35 mmol), and 1,4-diiodotetrafluorobenzene (240 mg, 0.39 mmol) were added to triethylamine (Et3N and tetrahydrofuran, 50 mL) under a nitrogen atmosphere and reacted overnight at 85 °C with magnetic stirring. The reaction mixture was cooled to room temperature, the solvent was then evaporated, and water and dichloromethane were added for extraction. The dichloromethane was then dried over anhydrous magnesium sulfate, and silica gel powder was added and the mixture was stirred. The sample was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 1:1, v / v) to give a white solid, designated (S)-1 (272 mg, 0.10 mmol, 26.6%).
[0056] 1 H NMR (400 MHz, CDCl3, 293 K) δ (ppm): 7.58 (d, J = 8.1 Hz, 2H), 7.41 (d, 2H), 6.99 (s, 2H), 6.34 (d, J = 7.7 Hz, 1H), 5.46-5.30 (m, 1H), 4.00 (m, 6H), 1.78 (m, 6H), 1.65 (d, J = 6.9 Hz, 3H), 1.46 (s, 6H), 1.25 (s, 48H), 0.87 (m, 9H).
[0057] [M+H] was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry. + The mass-to-charge ratio (m / z) of the ion is 1750.67.
[0058] Example 2
[0059] (R)-(+)-1-(4-bromophenyl)ethylamine was used instead of (S)-(+)-1-(4-bromophenyl)ethylamine in Example 1, and all other conditions were the same as in Example 1. The resulting white solid was the enantiomer compound, denoted as (R)-1 (284 mg, 0.11 mmol, 27.9%).
[0060] 1 H NMR (400 MHz, CDCl3, 293 K) δ (ppm): 7.58 (d, J = 8.1 Hz, 2H), 7.41 (d, 2H), 6.99 (s, 2H), 6.34 (d, J = 7.7 Hz, 1H), 5.46-5.30 (m, 1H), 4.00 (m, 6H), 1.78 (m, 6H), 1.65 (d, J = 6.9 Hz, 3H), 1.46 (s, 6H), 1.25 (s, 48H), 0.87 (m, 9H).
[0061] [M+H] was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry. + The mass-to-charge ratio (m / z) of the ion is 1749.42.
[0062] Example 3
[0063] Dichlorobis(triphenylphosphine)palladium (20 mg, 0.03 mmol), copper iodide (5 mg, 0.03 mmol), the second intermediate prepared in Example 1 (1080 mg, 1.35 mmol), and diiodobenzene (240 mg, 0.39 mmol) were added to triethylamine (Et3N and tetrahydrofuran, 50 mL) under a nitrogen atmosphere and reacted overnight at 85 °C with magnetic stirring. The reaction mixture was cooled to room temperature, the solvent was then evaporated, and water and dichloromethane were added for extraction. The dichloromethane was then dried over anhydrous magnesium sulfate, and silica gel powder was added and the mixture was stirred. The sample was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 1:1, v / v) to give a white solid, designated as (S)-2 (272 mg, 0.10 mmol, 26.6%).
[0064] 1 H NMR (400 MHz, CDCl3, 293 K) δ (ppm): 7.51 (d, 4H), 7.37 (d, 2H), 6.99 (s, 2H), 6.34 (d, J = 7.7 Hz, 1H), 5.46-5.30 (m, 1H), 4.00 (m, 6H), 1.78 (m, 6H), 1.65 (d, J= 6.9 Hz, 3H), 1.46 (s, 6H), 1.25 (s, 48H), 0.87 (m, 9H).
[0065] [M+H] was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry. + The mass-to-charge ratio (m / z) of the ion is 1677.89.
[0066] Example 4
[0067] (R)-(+)-1-(4-bromophenyl)ethylamine was used to replace (S)-(+)-1-(4-bromophenyl)ethylamine in Example 3, and all other conditions were the same as in Example 3. The resulting pale yellow solid was the enantiomer compound, denoted as (R)-2 (284 mg, 0.11 mmol, 27.9%).
[0068] 1 H NMR (400 MHz, CDCl3, 293 K) δ (ppm): 7.51 (d, 4H), 7.37 (d, 2H), 6.99 (s, 2H), 6.34 (d, J = 7.7 Hz, 1H), 5.46-5.30 (m, 1H), 4.00 (m, 6H), 1.78 (m, 6H), 1.65 (d, J= 6.9 Hz, 3H), 1.46 (s, 6H), 1.25 (s, 48H), 0.87 (m, 9H).
[0069] [M+H] was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry. + The mass-to-charge ratio (m / z) of the ion is 1678.38.
[0070] Example 5
[0071] Dichlorobis(triphenylphosphine)palladium (20 mg, 0.03 mmol), copper iodide (5 mg, 0.03 mmol), the second intermediate prepared in Example 1 (1080 mg, 1.35 mmol), and 1,4-diiodo-2,5-dimethyl ether (240 mg, 0.39 mmol) were added to triethylamine (Et3N and tetrahydrofuran, 50 mL) under a nitrogen atmosphere and reacted overnight at 85 °C with magnetic stirring. The reaction mixture was cooled to room temperature, the solvent was then evaporated, and water and dichloromethane were added for extraction. The dichloromethane was then dried over anhydrous magnesium sulfate, and silica gel powder was added and the mixture was stirred. The sample was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 1:1, v / v) to give a white solid, designated (S)-3 (272 mg, 0.10 mmol, 26.6%).
[0072] 1H NMR (400 MHz, CDCl3, 293 K) δ (ppm): 7.55 (d, 2H), 7.36 (d, 2H), 7.02 (s, 1H), 6.95 (s, 2H), 6.34 (d, J = 7.7 Hz, 1H), 5.46-5.30 (m, 1H), 4.00 (m, 6H), 3.89 (s, 3H), 1.78 (m, 6H), 1.65 (d, J = 6.9 Hz, 3H), 1.46 (s, 6H), 1.25 (s, 48H), 0.87 (m, 9H).
[0073] [M+H] was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry. + The mass-to-charge ratio (m / z) of the ion is 1737.52.
[0074] Example 6
[0075] (R)-(+)-1-(4-bromophenyl)ethylamine was used instead of (S)-(+)-1-(4-bromophenyl)ethylamine in Example 5, and all other conditions were the same as in Example 5. The resulting pale yellow solid was the enantiomer compound, denoted as (R)-3 (284 mg, 0.11 mmol, 27.9%).
[0076] 1 H NMR (400 MHz, CDCl3, 293 K) δ (ppm): 7.55 (d, 2H), 7.36 (d, 2H), 7.02 (s, 1H), 6.95 (s, 2H), 6.34 (d, J = 7.7 Hz, 1H), 5.46-5.30 (m, 1H), 4.00 (m, 6H), 3.89 (s, 3H), 1.78 (m, 6H), 1.65 (d, J = 6.9 Hz, 3H), 1.46 (s, 6H), 1.25 (s, 48H), 0.87 (m, 9H).
[0077] [M+H] was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry. + The mass-to-charge ratio (m / z) of the ion is 1737.62.
[0078] The arylacetylenes prepared in Examples 1-6 were dissolved in methylcyclohexane (MCH) to obtain arylacetylene supramolecular polymers with tunable circularly polarized luminescence. In this example, the concentration of the supramolecular polymer was controlled at 0.5 mM.
[0079] like Figure 8As shown in part (A), the arylacetylenic triphenylamine (R)-1 of the present invention assembles into a Wiener fiber supramolecular polymer through the synergistic effects of hydrogen bonding and π-π stacking, and due to the transfer of the alkyl stereocenter to the arylacetylenic core, a circular dichroism signal is obtained as shown in part (A). Figure 9 The solid blue line indicates that the arylaceyne chromophore polymer produces a fluorescence signal of 385 nm at an excitation wavelength of 300 nm. Figure 10 (A) portion of the blue curve), and the circular dichroism signal centered at 435 nm ( Figure 10 (B) Blue Curve). The resulting polymer, when subjected to ultrasound or stirring, forms a second type of nanofiber polymer (…). Figure 8 As shown in part (B), a circular dichroic signal inversion occurs simultaneously. Figure 9 (Partial red curve) and produces a 436 nm fluorescence signal at an excitation wavelength of 300 nm ( Figure 10 (A) part red curve), and the circular dichroism signal centered at 450 nm ( Figure 10 (B) section, red curve).
[0080] like Figure 11 As shown in part (A), the arylacetylenic triphenylamine (R)-2 of the present invention also assembles into a one-dimensional nanofiber supramolecular polymer under the synergistic effect of hydrogen bonding and π-π stacking, and due to the transfer of the alkyl stereocenter to the arylacetylenic core, the circular dichroism signal is as follows: Figure 12 Partial blue curves are shown. This is because the arylacetylene chromophore polymer produces a fluorescence signal of 376 nm at an excitation wavelength of 300 nm. Figure 13 (A) portion of the blue curve), and the circular dichroism signal centered at 378 nm ( Figure 13 (B) Partial blue curve). The resulting polymer, when subjected to ultrasound or stirring, forms a second type of nanofiber polymer ( Figure 11 As shown in part (B), a second type of circular dichromatic signal is generated simultaneously. Figure 12 (Partial red curve) and produces a fluorescence signal of 397 nm at an excitation wavelength of 300 nm ( Figure 13 (A) part red curve), and the circular dichroism signal centered at 396 nm ( Figure 13 (B) section, red curve).
[0081] like Figure 14 As shown, the arylacetylenic triphenylamine (R)-3 of the present invention also assembles into a one-way nanofiber supramolecular polymer under the synergistic effect of hydrogen bonding and π-π stacking, and due to the transfer of the alkyl stereocenter to the arylacetylenic core, the circular dichroism signal is as follows: Figure 15The blue curve in section (C) shows that the aryl acetylene chromophore polymer produces a fluorescence signal of 394 nm at an excitation wavelength of 300 nm. Figure 16 (A) portion of the blue curve), and the circular dichroism signal centered at 413 nm ( Figure 16 (Part B, blue curve).
[0082] In summary, arylacetylenes (R)-1, (R)-2, and (R)-3 exist in a supramolecular homologous polymer state. This results in circularly polarized emission at wavelengths of 378, 396, 413, 436, and 450 nm. The wavelength of the circularly polarized emission within the range of 378–450 nm is tunable; furthermore, the circular dichroism signals and circularly polarized emission of arylacetylenes (S)-1, (S)-2, and (S)-3 in the supramolecular polymer are symmetrical with those of (R)-1, (R)-2, and (R)-3.
[0083] Although embodiments of this application have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and variations can be made to these embodiments without departing from the principles and spirit of this application. The scope of this application is defined by the appended claims and their equivalents, all of which should be included within the protection scope of this application.
Claims
1. A arylacetylene supramolecular polymer with tunable circularly polarized luminescence, characterized in that, The structural formula of arylacetylene is as follows: A supramolecular polymer formed by the non-covalent interaction of arylacetylene dissolved in an organic solvent: ； In the formula, R1-R4 are all one of F, H and OCH3; The preparation steps of arylaceyne supramolecular polymers are as follows: S1: Methyl gallate and bromododecane are added to DMF and reacted to obtain compound A; S2: Compound A and sodium hydroxide are added to ethanol and reacted to give compound B; S3: Compound B, 1-(4-bromophenyl)ethylamine, 1-ethyl-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine were added to dichloromethane to react and prepare the first intermediate; S4: The first intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide and trimethylsilylacetylene are reacted with triethylamine under an inert atmosphere to obtain the second intermediate; S5: Arylacetylene is prepared by reacting a second intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide, and diiodine-substituted aromatic compounds with triethylamine under an inert atmosphere. S6: Dissolve arylaceyne in an organic solvent to obtain a arylaceyne supramolecular polymer with tunable circularly polarized luminescence.
2. The arylacetylene supramolecular polymer with tunable circularly polarized luminescence according to claim 1, characterized in that, The solvent is methylcyclohexane and / or cyclohexane.
3. The arylacetylene supramolecular polymer with tunable circularly polarized luminescence according to claim 1, characterized in that, The concentration of arylaceyne in organic solvents is 0.1-1 mM.
4. A method for preparing an arylacetylene supramolecular polymer with tunable circularly polarized luminescence, wherein the arylacetylene supramolecular polymer is as described in any one of claims 1-3, characterized in that... The steps are as follows: S1: Methyl gallate and bromododecane are added to DMF and reacted to obtain compound A; S2: Compound A and sodium hydroxide are added to ethanol and reacted to give compound B; S3: Compound B, 1-(4-bromophenyl)ethylamine, 1-ethyl-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine were added to dichloromethane to react and prepare the first intermediate; S4: The first intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide and trimethylsilylacetylene are reacted with triethylamine under an inert atmosphere to obtain the second intermediate; S5: Arylacetylene is prepared by reacting a second intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide, and diiodine-substituted aromatic compounds with triethylamine under an inert atmosphere. S6: Dissolve arylaceyne in an organic solvent to obtain a arylaceyne supramolecular polymer with tunable circularly polarized luminescence.
5. The method for preparing the circularly polarized luminescence-tunable arylaceyne supramolecular polymer according to claim 4, characterized in that, The molar ratio of methyl gallate to dodecane bromo in S1 is 1:4-8; And / or, the reaction temperature in S1 is 70-90℃, and the reaction time is 10-14 hours.
6. The method for preparing the circularly polarized luminescence-tunable arylaceyne supramolecular polymer according to claim 4, characterized in that, The molar ratio of compound A to sodium hydroxide in S2 is 1:6-10; And / or, the reaction temperature in S2 is 20-30℃, and the reaction time is 8-16 hours.
7. The method for preparing the circularly polarized luminescence-tunable arylaceyne supramolecular polymer according to claim 4, characterized in that, The molar ratio of compound B, 1-(4-bromophenyl)ethylamine, 1-ethyl-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine in S3 is 1:1-1.2:2.2-2.6:1.5-2; And / or, the reaction temperature in S3 is 25-35℃, and the reaction time is 10-18 hours.
8. The method for preparing the circularly polarized luminescence-tunable arylaceyne supramolecular polymer according to claim 4, characterized in that, The molar ratio of the first intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide, and trimethylsilylacetylene in S4 is 1:0.05-0.15:0.05-0.15:4-8. And / or, the reaction temperature in S4 is 75-85℃, and the reaction time is 12-16 hours.
9. The method for preparing the circularly polarized luminescence-tunable arylaceyne supramolecular polymer according to claim 4, characterized in that, The molar ratio of the second intermediate, dichlorobis(triphenylphosphine)palladium, copper iodide, and diiodosubstituted aromatic compounds in S5 is 1:0.005-0.02:0.01-0.03:0.5-0.55; And / or, the reaction temperature in S5 is 75-85℃, and the reaction time is 12-18 hours; And / or, the diiodine-substituted aromatic compound in S5 is one of diiodobenzene, 1,4-diiodotetrafluorobenzene, and 1,4-diiodo-2,5-dimethyl ether.
10. The application of a circularly polarized luminescent arylaceyne supramolecular polymer in circularly polarized luminescent materials, characterized in that, The arylaceyne supramolecular polymer is as described in any one of claims 1-3.