Search

CN-121718034-B - Circular polarized luminescence adjustable aryl acetylene supermolecular polymer, preparation and application

CN121718034BCN 121718034 BCN121718034 BCN 121718034BCN-121718034-B

Abstract

The invention discloses an aryl acetylene supermolecular polymer with controllable circular polarized luminescence, a preparation method and an application thereof, and relates to the technical field of circular polarized luminescent materials, wherein the specific preparation method comprises the following steps of reacting methyl gallate with bromododecane to obtain a compound A; the method comprises the steps of reacting a compound A with sodium hydroxide to obtain a compound B, reacting the compound B, 1- (4-bromophenyl) ethylamine, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and 4-dimethylaminopyridine to obtain a first intermediate, reacting the first intermediate, dichloro-bis (triphenylphosphine) palladium, copper iodide and trimethylsilylacetylene to obtain a second intermediate, reacting the second intermediate, dichloro-bis (triphenylphosphine) palladium, copper iodide and diiodo-substituted aromatic compounds to obtain aryl acetylene, and dissolving the aryl acetylene in an organic solvent to obtain the circular polarization luminescence-adjustable aryl acetylene supermolecular polymer S6. The present invention developed CPL materials with tunable properties.

Inventors

  • HUANG YUN
  • HUANG NINGDONG
  • WANG FENG

Assignees

  • 中国科学技术大学

Dates

Publication Date
20260512
Application Date
20260213

Claims (10)

  1. 1. The circular polarized luminescence controllable aryl acetylene supermolecular polymer is characterized in that aryl acetylene is dissolved in an organic solvent to form the supermolecular polymer through non-covalent action, and the structural formula of the aryl acetylene is as follows: ; Wherein R 1 -R 4 is one of F, H and OCH 3 ; The preparation method of the aryl acetylene supermolecular polymer comprises the following steps: s1, adding methyl gallate and bromododecane into DMF (dimethyl formamide) for reaction to obtain a compound A; S2, adding the compound A and sodium hydroxide into ethanol to react to obtain a compound B; S3, adding a compound B, 1- (4-bromophenyl) ethylamine, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and 4-dimethylaminopyridine into dichloromethane to react to prepare a first intermediate; S4, adding the first intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and trimethylsilyl acetylene into triethylamine under inert atmosphere for reaction to prepare a second intermediate; s5, adding a second intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and a diiodide-substituted aromatic compound into triethylamine in an inert atmosphere for reaction to prepare aryl acetylene; S6, dissolving the aryl acetylene in an organic solvent to obtain the circular polarized luminescence adjustable aryl acetylene supermolecular polymer.
  2. 2. The circularly polarized light emitting regulatable arylacetylene supermolecular polymer according to claim 1, wherein the solvent is methylcyclohexane and/or cyclohexane.
  3. 3. The circularly polarized light-emitting regulatable arylacetylene supermolecular polymer of claim 1, wherein the concentration of arylacetylene in the organic solvent is 0.1-1 mM.
  4. 4. A method for preparing an arylacetylene supermolecular polymer with controllable circular polarized luminescence, which is characterized in that the method comprises the following steps: s1, adding methyl gallate and bromododecane into DMF (dimethyl formamide) for reaction to obtain a compound A; S2, adding the compound A and sodium hydroxide into ethanol to react to obtain a compound B; S3, adding a compound B, 1- (4-bromophenyl) ethylamine, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and 4-dimethylaminopyridine into dichloromethane to react to prepare a first intermediate; S4, adding the first intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and trimethylsilyl acetylene into triethylamine under inert atmosphere for reaction to prepare a second intermediate; s5, adding a second intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and a diiodide-substituted aromatic compound into triethylamine in an inert atmosphere for reaction to prepare aryl acetylene; S6, dissolving the aryl acetylene in an organic solvent to obtain the circular polarized luminescence adjustable aryl acetylene supermolecular polymer.
  5. 5. The method for preparing the circularly polarized light-emitting adjustable aryl acetylene supermolecular polymer according to claim 4, wherein the molar ratio of the methyl gallate to the bromododecane 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. 6. The method for preparing the circularly polarized light-emitting adjustable aryl acetylene supermolecular polymer according to claim 4, wherein the molar ratio of the compound A to the 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. 7. The method for preparing the circularly polarized light emission adjustable arylacetylene supermolecular polymer according to claim 4, wherein the molar ratio of the 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. 8. The method for preparing the circularly polarized light-emitting adjustable aryl acetylene supermolecular polymer according to claim 4, wherein the molar ratio of the first intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and trimethylsilyl acetylene 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. 9. The method for preparing the circularly polarized light-emitting adjustable aryl acetylene supermolecular polymer according to claim 4, wherein the molar ratio of the second intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and diiodide-substituted aromatic compound 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 aromatic compound substituted by diiodide in S5 is one of diiodobenzene, 1, 4-diiodotetrafluorobenzene and 1, 4-diiodine-2, 5-dimethyl ether.
  10. 10. Use of a circularly polarized light emitting regulatable arylacetylene supermolecular polymer in a circularly polarized light emitting material, characterized in that the arylacetylene supermolecular polymer is as defined in any one of claims 1-3.

Description

Circular polarized luminescence adjustable aryl acetylene supermolecular polymer, preparation and application Technical Field The invention relates to the technical field of circularly polarized luminescent materials, in particular to a circularly polarized luminescent adjustable aryl acetylene supermolecular polymer, and preparation and application thereof. Background Adjusting the wavelength of Circularly Polarized Light (CPL) is important to expand the application of the CPL in the fields of optical devices, information encryption and the like. The construction of CPL active materials based on pi conjugated aromatic chromophores is a common strategy for realizing efficient luminescence. At present, two main ways of regulating CPL wavelength are to introduce specific functional groups into chromophore through chemical modification to change its electronic structure and energy level distribution, and to regulate molecule stacking mode via supermolecule interaction to influence excited state property. However, the former is often complicated in synthesis steps and difficult to precisely control the luminescence property, while the latter is sensitive to external conditions, and the stability of the assembly is often insufficient, both of which have certain limitations. Disclosure of Invention Based on the technical problems in the background technology, the invention provides a circular polarization luminescence adjustable aryl acetylene supermolecular polymer, preparation and application thereof, and develops a CPL material with adjustable characteristics. The invention provides a circular polarized luminescence adjustable aryl acetylene supermolecular polymer, which is formed by dissolving aryl acetylene in an organic solvent and through non-covalent action, wherein the structural formula of the aryl acetylene is as follows: Wherein R 1-R4 is one of F, H and OCH 3. Preferably, the solvent is methylcyclohexane and/or cyclohexane. Preferably, the concentration of aryl acetylene in the organic solvent is from 0.1 to 1 mM. The invention provides a preparation method of a circular polarization luminescence-adjustable aryl acetylene supermolecular polymer, which comprises the following steps: s1, adding methyl gallate and bromododecane into DMF (dimethyl formamide) for reaction to obtain a compound A; S2, adding the compound A and sodium hydroxide into ethanol to react to obtain a compound B; S3, adding a compound B, 1- (4-bromophenyl) ethylamine, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and 4-dimethylaminopyridine into dichloromethane to react to prepare a first intermediate; S4, adding the first intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and trimethylsilyl acetylene into triethylamine under inert atmosphere for reaction to prepare a second intermediate; s5, adding a second intermediate, dichloro bis (triphenylphosphine) palladium, copper iodide and a diiodide-substituted aromatic compound into triethylamine in an inert atmosphere for reaction to prepare aryl acetylene; S6, dissolving the aryl acetylene in an organic solvent to obtain the circular polarized luminescence adjustable aryl acetylene supermolecular polymer. Preferably, the molar ratio of the methyl gallate to the bromododecane in the S1 is 1:4-8; And/or the reaction temperature in S1 is 70-90 ℃ and the reaction time is 10-14 hours. Preferably, 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. 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; And/or the reaction temperature in S3 is 25-35 ℃ and the reaction time is 10-18 hours. Preferably, the molar ratio of the first intermediate in S4, the dichloro bis (triphenylphosphine) palladium, the copper iodide and the trimethylsilyl acetylene 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. Preferably, the molar ratio of the second intermediate, dichlorobis (triphenylphosphine) palladium, copper iodide and diiodo-substituted aromatic compound 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. Preferably, the diiodo-substituted aromatic compound in S5 is one of diiodobenzene, 1, 4-diiodotetrafluorobenzene and 1, 4-diiodo-2, 5-dimethyl ether. The invention provides an application of a circular polarization luminescence adjustable aryl acetylene supermolecular polymer in a circular polarization luminescent material, wherein the aryl acetylene supermolecular polymer is as described above. The beneficial technical effects of the invention are as follows: (1) The invention provides a novel circularly polarized light emitting supermolecular polymer material and a preparation method thereof, and a supermolec