Circularly polarized light-emitting organic micro-nano crystal material as well as preparation method and application thereof

A crystalline material and circular polarization technology, applied in the field of circularly polarized light-emitting organic micro-nano crystal materials and their preparation, can solve the problems of complex molecular structure, long and tedious preparation process, etc. Effect

Active Publication Date: 2021-06-22
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
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Problems solved by technology

[0004] Aiming at the problems in the prior art that the general molecular structure of materials with circularly polarized luminescent properties is very complex and the preparation process is relatively tedious and cumbersome, the present invention provides a circularly polarized luminescent organic micro-nano crystal material based on pyridine groups and its preparation The method and application can broaden the research direction for the preparation of circularly polarized light-emitting organic materials

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  • Circularly polarized light-emitting organic micro-nano crystal material as well as preparation method and application thereof
  • Circularly polarized light-emitting organic micro-nano crystal material as well as preparation method and application thereof
  • Circularly polarized light-emitting organic micro-nano crystal material as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0102] This embodiment provides an ionic protonated pyridinium salt compound as shown in formula I-1 and a preparation method thereof.

[0103]

[0104] The preparation method of the ionic protonated pyridinium salt compound comprises the following steps:

[0105] (1) Preparation of 2,2'-bis(2-pyridine)-1,1'-biphenyl:

[0106] The synthesis of 2,2'-bis(2-pyridine)-1,1'-biphenyl refers to the reaction formula (1-1) Guo X, Wang G, Li C-J.Ruthenium-Catalyzed Oxidative Homo-Coupling of 2-Arylpyridines[ J]. Adv. Syn. Cat. 2009, 351:2071-2074.

[0107]

[0108] (2) Preparation of ionic protonated pyridinium salt complexes as shown in formula I-1a:

[0109]

[0110] A solution of 2,2'-bis(2-pyridine)-1,1'-biphenyl (6.9 mg, 0.022 mmol) in tetrahydrofuran (1 mL) and levocamphorsulfonic acid (L-(-)-CSA) (10.2 mg , 0.044mmol) tetrahydrofuran solution (2mL) uniformly mixed, 70W water bath ultrasonic 2min, room temperature for 10min, filtered the white precipitated solid to obt...

Embodiment 2

[0122] This embodiment provides an ionic protonated pyridinium salt compound as shown in formula I-2 and a preparation method thereof.

[0123]

[0124] Its preparation method comprises the following steps:

[0125] (1) Preparation of 2,2'-bis(4-bromo-2-pyridine)-1,1'-biphenyl;

[0126] Dimer of p-cymene dichloride ruthenium (76.5mg, 0.13mmol), 4-bromo-2-phenylpyridine (1170mg, 5.0mmol), ferric chloride (649mg, 4.0mmol) and 15mL of chlorobenzene Added to a 100mL oven-dried reaction vessel, stirred at 120°C for 16h. After cooling to room temperature, 12mL Et 3 N and 12mL CH 2 Cl 2 Added to the reaction system, and continued to stir at room temperature for 0.5h. The resulting mixture was treated with CH 2 Cl 2 Diluted short silica gel column was filtered, the filtrate was concentrated, and the residue was purified by column chromatography (SiO 2, PE / EA=5:1, v / v), 550 mg of white solid was obtained, the yield was 64%.

[0127] The main reaction path is shown in reacti...

Embodiment 3

[0153] This embodiment provides an ionic protonated pyridinium salt compound as shown in formula I-3 and a preparation method thereof.

[0154]

[0155] The preparation method of this compound comprises the following steps:

[0156] (1) Preparation of 2,2'-bis(4-((E)-4-methoxystyrene)-2-pyridine)-1,1'-biphenyl:

[0157] in N 2 Under protection, 2,2'-bis(4-bromo-2-pyridine)-1,1'-biphenyl (322mg, 0.69mmol), K 2 CO 3 (193mg, 1.4mmol) and Pd(OAc) 2 (18mg, 0.08mmol) was added to an oven-dried 100mL round bottom flask, and 1-methoxy-4-vinylbenzene (375μL, 2.8mmol) and DMF (8mL) were added with a syringe, and nitrogen was bubbled at room temperature to remove oxygen for 20min After that, add PPh 3 Ligand (56mg, 0.21mmol), the reaction system was sealed and placed in an oil bath preheated to 140°C, and stirred at this temperature for 48h. After cooling to room temperature, the reaction mixture was poured into water (10 mL) and washed with CH 2 Cl 2 (3 x 20 mL) extraction. ...

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Abstract

The invention provides a circularly polarized light-emitting organic micro-nano crystal material as well as a preparation method and application thereof, belongs to the technical field of organic light-emitting materials, and aims to solve the problems that materials with circularly polarized light-emitting performance in the prior art are generally very complex in molecular structure and relatively long and tedious in preparation process. The circularly polarized light-emitting organic micro-nano crystal is an ionic pyridinium salt compound, and the structural formula is shown as a formula I in the specification; the ionic pyridinium salt compound is composed of positive ions of 2, 2'-bis(2-pyridine)-1, 1'-biphenyl or derivatives thereof and negative ions of camphorsulfonate radicals; and in the formula I, * represents chirality of the camphorsulfonate radicals, the camphorsulfonate radicals are left-handed (L) or right-handed (D), and R groups are H or aromatic substituent groups with different conjugate lengths. According to the method, the high-quality circularly polarized light-emitting two-dimensional micro-nano crystal is prepared in situ through a simple and rapid one-step solution reprecipitation method. The organic micro-nano crystal material can be applied to the fields of optical sensing and the like.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a circularly polarized light-emitting organic micro-nano crystal material and a preparation method and application thereof. Background technique [0002] In recent years, circularly polarized luminescent nanomaterials have attracted extensive attention due to their potential applications in optoelectronic devices, optical sensors, asymmetric synthetic catalysts, etc. Many reports have demonstrated that supramolecular assembly can precisely control and enhance the circular polarization properties of chiral and even achiral chromophores. Therefore, based on intermolecular non-covalent interactions, including hydrogen bonding, π-π stacking, electrostatic and Hydrophobic interactions construct a variety of circularly polarized light-emitting organic nanoassemblies. Unlike flexible nanoassemblies based on gelling agents, polymers, metal complexes, liquid crys...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07C309/19C07C303/32C09K11/06
CPCC07D213/61C07C309/19C07C303/32C09K11/06C07B2200/07C07C2602/42C09K2211/1029
Inventor 钟羽武李仲秋
Owner INST OF CHEM CHINESE ACAD OF SCI
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