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Chiral dark blue fluorescent material and preparation method thereof

A fluorescent material and deep blue technology, which is applied in the field of chiral fluorescent materials emitting deep blue fluorescence and their preparation, can solve the problems of difficulty in obtaining deep blue and deep red fluorescent materials, low activity, and difficulty in reaction, and achieve high solid state The effect of luminous efficiency and strong fluorescence intensity

Active Publication Date: 2020-06-30
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are three main reasons why dark blue and deep red fluorescent materials are rare: (1) there is no suitable skeleton that can be modified; (2) the reaction is difficult to proceed due to steric hindrance; (3) due to electron donation or absorption The activity of electron groups is low and the reaction conditions are relatively harsh, so it is difficult to obtain the target dark blue and deep red fluorescent materials

Method used

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  • Chiral dark blue fluorescent material and preparation method thereof
  • Chiral dark blue fluorescent material and preparation method thereof
  • Chiral dark blue fluorescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 313mg (0.5mmol) of compound I-1, 434mg (1.5mmol) of triphenylamine-4-boronic acid, 58mg (0.05mmol) of tetrakis(triphenylphosphine)palladium into 3mL of ethylene glycol dimethyl ether, and add 2mol / L carbonic acid Potassium aqueous solution adjusts the pH value of the system to 8-9, stirs and reacts at 80°C for 16 hours, extracts the reaction solution with dichloromethane, combines the organic phases, and performs dry column chromatography (the volume ratio of petroleum ether to ethyl acetate is 60: 1 as the eluent) to obtain compound II-1 with a yield of 78%.

[0035]

[0036] The structural characterization data of the resulting product are: 1 H NMR (300MHz, CDCl 3 )δ7.96(s,1H),7.88(d,J=8.2Hz,1H),7.64(d,J=8.6Hz,2H),7.41(ddd,J=8.1,5.2,2.8Hz,1H), 7.28(dd, J=5.6,2.4Hz,4H),7.24(s,2H),7.15(t,J=8.6Hz,6H),7.03(t,J=7.3Hz,2H),4.46(dd,J =13.7,5.7Hz,2H),2.45(s,3H).

Embodiment 2

[0038] 1. Compound II-1 was prepared according to the method of Example 1.

[0039] 2. Add 300mg (0.35mmol) of compound II-1, 292mg (0.86mmol) of 1,3-diiodo-5,5-dimethylhydantoin, and 18mg (0.035mmol) of scandium trifluoride into 8mL of dichloromethane , stirred at room temperature for 12 hours, dry column chromatography (the mixture of petroleum ether and ethyl acetate with a volume ratio of 60:1 was used as the eluent), and compound III-1 was obtained.

[0040]

[0041] 3. Add 334 mg (0.3 mmol) of compound III-1, 110 mg (0.9 mmol) of phenylboronic acid (compound IV-1), and 35 mg (0.03 mmol) of tetrakis(triphenylphosphine) palladium into 2 mL of ethyl alcohol dimethyl ether, and add 2mol / L potassium carbonate aqueous solution adjusts the pH value of the system to 8-9, stirs and reacts at 80°C for 16 hours, extracts the reaction solution with dichloromethane, combines the organic phases, and performs dry column chromatography (petroleum ether and ethyl acetate volume The m...

Embodiment 3

[0045]Add 566mg (1.0mmol) of compound I-2, 867mg (3.0mmol) of triphenylamine-4-boronic acid, and 116mg (0.1mmol) of tetrakis(triphenylphosphine)palladium into 8mL of ethylene glycol dimethyl ether, and add 2mol / The pH value of L potassium carbonate aqueous solution adjustment system is 8 ~ 9, stirred and reacted at 80 DEG C for 16 hours, extracted the reaction solution with dichloromethane, combined the organic phase, and performed dry column chromatography (the volume ratio of sherwood oil and ethyl acetate was 60:1 mixture was the eluent) to obtain compound II-2 with a yield of 87%.

[0046]

[0047] The structural characterization data of the resulting product are: 1 H NMR (300MHz, CDCl 3 )δ7.97(s,1H),7.89(d,J=8.1Hz,1H),7.64(d,J=8.5Hz,2H),7.42-7.34(m,1H),7.29(s,1H), 7.22(d, J=6.5Hz, 4H), 7.15(d, J=8.2Hz, 7H), 7.02(t, J=7.2Hz, 2H), 3.24(s, 3H).

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Abstract

The invention discloses a class of chiral dark blue fluorescent materials and a preparation method thereof. In the structural general formula of the fluorescent material, R1 represents methyl methyl ether or C1-C3 alkyl, and R2 represents any one of H, phenyl, C1-C2 alkoxy substituted phenyl, C1-C3 alkyl substituted phenyl and triphenylamino. According to the preparation method, hydroxyl-protected3,3'-iodo-o-dinaphthol and triphenylamine-4-boric acid are utilized to synthesize an o-dinaphthol intermediate, and then a Suzuki coupling reaction is utilized to synthesize the final fluorescent material. The fluorescent material provided by the invention realizes dark blue fluorescence luminescence characteristics and chirality in one molecular skeleton at the same time, can be used for preparing organic light emitting devices and chiral light emitting devices, has strong fluorescence intensity in an organic solvent and water, has high solid-state luminous efficiency, and can realize imaging of cells, tissues and bacteria, glycosylation analysis of proteins, detection of ions and the like.

Description

technical field [0001] The invention belongs to the technical field of chiral fluorescent materials, and in particular relates to a chiral fluorescent material emitting deep blue fluorescence and a preparation method thereof. Background technique [0002] Due to the wide application of fluorescent materials, such as dyes, organic pigments, anti-counterfeiting marks, cell labels, organic light-emitting diodes, cell surface protein labels, and the removal of biological tumors, fluorescent materials have received more and more scientific attention in recent years. world's attention. According to relevant literature and related mechanisms, the synthesis and emission of different fluorescent materials requires the adjustment of the strength and position of electron donation and electron withdrawal on the basis of the basic skeleton. At present, the emission wavelength of most fluorescent materials is between 480nm and 650nm, and the dark blue below 480nm Color and deep red fluor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/78C07C213/02C07C213/08C09K11/06
CPCC07C217/78C07C213/02C07C213/08C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C07B2200/07
Inventor 李楠赵娜张敏
Owner SHAANXI NORMAL UNIV
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