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Axial chiral azahelicene derivative, circular polarization luminescent material and preparation method

A technology of azahelicene and luminescent materials, applied in luminescent materials, organic chemical methods, chemical instruments and methods, etc., can solve the problem of low asymmetry factor, reduce difficulty, excellent chiral luminescence performance, and expand the selection range Effect

Active Publication Date: 2020-09-08
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the asymmetry factor (glum) of the circularly polarized luminescence of common chiral organic fluorescent molecules is low

Method used

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  • Axial chiral azahelicene derivative, circular polarization luminescent material and preparation method
  • Axial chiral azahelicene derivative, circular polarization luminescent material and preparation method
  • Axial chiral azahelicene derivative, circular polarization luminescent material and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] This embodiment relates to the method for preparing racemic azahelicene A, as follows:

[0044]

[0045] The reaction principle is as figure 1 As shown, it specifically includes the following steps: 2.4g of 2-methyl[4]helicene bromotriphenylphosphine salt is dissolved in 20mL of tetrahydrofuran dehydrated, and cooled to -78°C with an ice ethanol bath under nitrogen protection. Slowly add 2.8 mL of n-butyllithium (1.6 mol / L n-hexane solution) to the reaction system, react at -78°C for 5 minutes, then slowly raise the temperature to room temperature for 30 minutes. As the reaction progressed, the reaction system gradually turned dark red. Then the reaction system was cooled to -78°C with an ice ethanol bath, and 628 mg of 6-formylquinoline was added thereto, reacted at -78°C for 5 minutes, and then slowly warmed up to room temperature for 60 minutes. After the reaction was completed, the solvent was removed and then purified with a silica gel column (eluent: ethyl ac...

Embodiment 2

[0049] This embodiment relates to the method for preparing chiral azahelicene, the process is as follows:

[0050]

[0051] Specifically, chiral resolution is performed using a high-performance liquid chromatography chiral column, and the specific chiral column is a CHIRALPAKIG preparative column; the mobile phase is n-hexane / ethanol=80 / 20 (v / v); the P-type isomer is obtained by resolution I (e.e. >99%) and M-type isomer II (e.e. >99%).

[0052] The high-performance liquid chromatography data of this compound are shown in table 1 and table 2, and relevant spectrogram sees Figure 4 with Figure 5 shown;

[0053] Table 1, the high performance liquid chromatography data of compound I

[0054] compound Ret. Time area Area% T.Plate# I 4.949 3111176 99.9797 654.005 II 5.812 630 0.0203 12499.444

[0055] Table 2, HPLC data of compound II

[0056] compound Ret. Time area Area% T.Plate# I 4.951 1629 0.0399 5651.0...

Embodiment 3

[0060] This embodiment relates to a preparation method of azahelicene quaternary ammonium salt, such as Figure 8 As shown, it specifically includes the following steps: Preparation of Compound B: Weigh 38 mg of Compound A, add about 0.2 mL of methyl iodide, and react for 24 hours under stirring at room temperature. After the reaction was completed, 50 mg of an orange solid was obtained after removal of iodomethane, with a yield of 96%.

[0061] Chiral compounds III and IV can be obtained by the same method using compounds I and II as reactants, and the yields are 98% and 94%, respectively.

[0062] The characterization results of compound B are as follows:

[0063] 1 H NMR (500MHz, DMSO-d6, 295K): δ8.78(d, J=5.6Hz, 1H), 8.73(d, J=9.2Hz, 1H), 8.48(d, J=8.2Hz, 1H), 8.40(d,J=8.2Hz,1H),8.34(d,J=8.3Hz,2H),8.31-8.24(m,2H),8.21(d,J=9.2Hz,2H),7.99(d,J =8.5Hz, 1H), 7.72(d, J=8.5Hz, 1H), 7.51(d, J=7.9Hz, 1H), 7.12(t, J=7.4Hz, 1H), 7.03-6.92(m, 2H ), 6.49(t, J=7.6Hz, 1H), 4.36(s, 3...

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Abstract

The invention relates to an axial chiral azaspirene derivative, a circular polarization luminescent material and a preparation method. The structural formula of a racemate of the axial chiral azahelicene is shown as formula A, the structural formula of a P-type isomer is shown as formula I, the structural formula of an M-type isomer is shown as formula II, a compound shown as formula A or a P-typeisomer shown as formula I or an M-type isomer shown as formula II is taken as a reactant for normal temperature stirring reaction with excessive methyl iodide for 24 hours at under the condition of no additional other solvent, so that the product axial chiral azaspirene derivative can be obtained. The compound is compounded with DNA to form a DNA-helicene compound which can be used as a circularpolarization luminescent material. Compared with the prior art, the method has the advantages of simple synthesis method, high synthesis yield and the like.

Description

technical field [0001] The invention belongs to the field of luminescent materials, and relates to a method for inducing achiral / racemic condensed ring molecules and enhancing circularly polarized luminescence of the chiral fused ring molecules. Background technique [0002] In recent years, the research enthusiasm of circularly polarized luminescent materials has been increasing. Circular polarization materials have attracted the attention of scientists because of their good application prospects in many fields including optical display, information storage, optoelectronic devices, and biological imaging. Chiral organic fluorescent molecules with circularly polarized luminescent properties have always been a research hotspot in the field of chiral luminescent materials because of their unique chiral luminescent properties and broad application prospects. [0003] At present, the circularly polarized luminescence of chiral organic fluorescent molecules has great limitations...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C09K11/06
CPCC07D221/18C09K11/06C07B2200/07C09K2211/1029
Inventor 邱惠斌沈程硕干富伟
Owner SHANGHAI JIAO TONG UNIV
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