A chiral organic dye molecule with circularly polarized luminescent properties and its preparation method and application

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

Active Publication Date: 2018-10-09
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A chiral organic dye molecule with circularly polarized luminescent properties and its preparation method and application
  • A chiral organic dye molecule with circularly polarized luminescent properties and its preparation method and application
  • A chiral organic dye molecule with circularly polarized luminescent properties and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1, the compound shown in preparation formula D

[0087] The reaction formula is as follows:

[0088]

[0089] 1) Add 159gA, 49g maleic anhydride and 500ml xylene successively in a 1000ml round-bottomed flask, heat and reflux for 10 hours, remove the xylene from the reaction system by steam distillation, after the remaining solid is dried, recrystallize with 500ml acetic anhydride, filter 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 liquid bromine in 50ml of acetic acid, put it in a dropping funnel, slowly drop it into the flask at room temperature, and filter it after 12 hours , washed with a small amount of dichloromethane to obtain 9.1 g of oxidative addition product C, with a yield of 80%;

[0091] 3) Add 5.98g (0.01mol) of oxidative addition product C and 5.9g (0.1mol) of n-propylamine to a 250ml round botto...

Embodiment 2

[0097] Embodiment 2, compound shown in preparation formula E and formula F

[0098] The reaction formula is as follows:

[0099]

[0100] 1) Utilize high-performance liquid chromatography (HPLC) chiral column to carry out resolution, and specific chiral column is IC semi-preparative column; mobile phase is CO 2 / MeOH / DCM=40 / 30 / 30 (v / v / v); resolution gave 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 relevant spectrogram sees 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] From the above detection results, it can be seen that the obtained chiral compound has a correct structure.

Embodiment 3

[0107] Embodiment 3, preparation of the formula G of the compound shown in the attributable formula G 1 Compound shown

[0108] The reaction formula is as follows:

[0109]

[0110] Add 61mgE and 57mg p-trifluoromethylbenzeneboronic acid into a 25ml two-necked bottle, add 5ml toluene, 3ml ethanol and 2ml 2mol / LNa with a syringe under the protection of argon 2 CO 3 Aqueous solution, add catalyst tetrakis (triphenylphosphine) palladium 5mg after ventilating for 5 minutes, reflux at 100°C for 12 hours, take the organic layer, MgSO 4 Dried, filtered, spin-dried, separated by column chromatography to obtain the G substituted by trifluoromethylphenyl 1 44mg.

[0111] The structure detection result of this compound is 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 ...

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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 circularly polarized light emission, a preparation method and application thereof. Background technique [0002] Due to the chiral organic dye molecules have both chiral and photophysical and electrochemical properties, research in the fields of chiral light-emitting diodes, chiral field-effect transistors, chiral fluorescence imaging, and fluorescence and electrochemical sensors has been receiving much attention in recent years. Scientists favor chiral organic dye molecules with circularly polarized luminescence (CPL) properties because of 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 molecules in optoelectronic devices is very limited, mainly due to the...

Claims

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Application Information

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