Chiral organic dye molecules having circularly polarized luminescence properties as well as preparation method and application of chiral organic dye molecules

A cross-coupling reaction and compound technology, applied in the field of dyes, can solve the problems of difficult preparation, limited development of chiral optoelectronic devices, and limited application, and achieve good application prospects, cheap raw materials, and simple synthesis methods

Active Publication Date: 2016-10-12
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Compared with the wide application of traditional organic dye molecules in the research fields of organic functional materials and devices, the application of chiral dye molecules in optoelectronic devices is very limited, mainly due to the lack of types of chiral organic dye molecules that limit chirality. The development of optoelectronic devices
At present, the main strategy to obtain chiral organic dye molecules is to introduce chiral groups into simple organic dye molecules, but it is often limited by the difficulty of preparation and the availability of species.

Method used

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  • Chiral organic dye molecules having circularly polarized luminescence properties as well as preparation method and application of chiral organic dye molecules
  • Chiral organic dye molecules having circularly polarized luminescence properties as well as preparation method and application of chiral organic dye molecules
  • Chiral organic dye molecules having circularly polarized luminescence properties as well as preparation method and application of chiral organic dye molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Example 1. Preparation of compound represented by formula D

[0087] The reaction formula is as follows:

[0088]

[0089] 1) Add 159gA, 49g maleic anhydride and 500ml xylene in a 1000ml round-bottomed flask successively, and heat to reflux for 10 hours. The reaction system is steam distilled to remove xylene. After the remaining solid is dried, it is recrystallized with 500ml acetic anhydride and filtered to obtain 87.8 g Acid anhydride addition product B, the yield is 82%;

[0090] 2) Add 8.3g of addition product B and 40ml of dichloromethane into a 250ml round bottom flask, dissolve 3ml of bromine in 50ml of acetic acid, place it in a dropping funnel, and slowly drip into the flask at room temperature. After 12 hours, filter , Washed with a small amount of dichloromethane to obtain 9.1g of oxidation addition product C, with a yield of 80%;

[0091] 3) Add 5.98g (0.01mol) of oxidation addition product C and 5.9g (0.1mol) of n-propylamine into a 250ml round bottom flask, heat...

Embodiment 2

[0097] Example 2. Preparation of compounds represented by formula E and formula F

[0098] The reaction formula is as follows:

[0099]

[0100] 1) Use high performance liquid chromatography (HPLC) chiral column for resolution, the specific chiral column is IC semi-preparative column; mobile phase is CO 2 / MeOH / DCM=40 / 30 / 30(v / v / v); split to obtain E(e.e.> 99%) and F(e.e.> 99%).

[0101] The high performance liquid chromatography data of this compound are shown in Table 1 and Table 2, and the relevant spectra are shown in Figure 7 with Figure 8 Shown:

[0102] Table 1. HPLC data of E

[0103] Compound

Ret.Time

Area

Area%

T.Plate#

Height

Height%

E

2.613

8805505

100.00

993952

100.00

2.613

[0104] Table 2. HPLC data of F

[0105]

[0106] It can be seen from the above detection results that the chiral compound has a correct structure.

Embodiment 3

[0107] Example 3. Preparation of formula G belonging to the compound represented by formula G 1 Shown compound

[0108] The reaction formula is as follows:

[0109]

[0110] Take 61mg E and 57mg p-trifluoromethyl phenylboronic acid into a 25ml two-necked flask, add 5ml toluene, 3ml ethanol and 2ml 2mol / LNa with a syringe under the protection of argon. 2 CO 3 Aqueous solution, ventilate for 5 minutes, add 5mg of tetrakis(triphenylphosphonium) palladium catalyst, reflux for 12 hours at 100℃, take the organic layer, MgSO 4 Dry, filter, spin-dry, and separate by column chromatography to obtain p-trifluoromethylphenyl substituted G 1 44mg.

[0111] The structure test results of this compound are as follows:

[0112] 1 H NMR(500MHz, CDCl 3 )δ7.75–7.61(m,8H),7.27(s,2H),4.19–4.14(m,2H), 3.73–3.64(m,2H), 3.20(s,6H),3.02–2.98(m, 2H), 2.73(td,J=14.6,3.9Hz,2H), 2.53(td,J=15.3,3.9Hz,2H), 1.75(h,J=7.4Hz,2H),1.33(s,6H), 1.00(t,J=7.4Hz,3H). 13 C NMR(126MHz, CDCl 3 )δ169.0, 155.5, 141.9, 139.2, 139.0...

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Abstract

The invention discloses chiral organic dye molecules having circularly polarized luminescence properties as well as a preparation method and an application of the chiral organic dye molecules. The chiral organic dye molecules have structural formulas shown in the formula I1 and the formula I2. Chiral organic dyes shown in the formula I1 and the formula I2 can be used for preparing chiral organic luminescent materials, and the organic luminescent materials have multi-color circularly polarized luminescence properties. According to the method for preparing the chiral organic dyes having the multi-color circularly polarized luminescence properties, raw materials are cheap, the synthesis method is simple, the yield of products is high, and the organic dyes have the characteristic of easiness in derivatization, are good in stability and have the bright application prospect in the field of chiral photoelectric materials.

Description

Technical field [0001] The invention belongs to the field of dyes, and relates to a chiral organic dye molecule with circular polarization luminescence, and a preparation method and application thereof. Background technique [0002] Chiral organic dye molecules have both chiral and photophysical and electrochemical properties. In recent years, research in fields including chiral light-emitting diodes, chiral field-effect transistors, chiral fluorescence imaging, and fluorescence and electrochemical sensors has been extensively studied. Favored by scientists, chiral organic dye molecules with circularly polarized luminescence (CPL) properties have always been a research hotspot in the field of chiral luminescent materials due to their unique chiral luminescence properties and wide application prospects. [0003] Compared with the wide application of traditional organic dye molecules in the research fields of organic functional materials and devices, the application of chiral dye mol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/58C09K11/06C09B57/00
CPCC07B2200/07C07D209/58C09B57/00C09K11/06C09K2211/1029
Inventor 李猛陈传峰
Owner INST OF CHEM CHINESE ACAD OF SCI
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