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Aggregation-induced emission type near-infrared fluorescent material and synthesis method thereof

A technology for aggregation-induced luminescence and fluorescent materials, applied in the field of preparation of the materials

Active Publication Date: 2020-07-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional near-infrared fluorescent dyes usually have a large rigid planar structure, and are prone to π-π stacking at high concentrations or aggregation states, resulting in fluorescence quenching (Aggregation-caused quenching, ACQ), and organic molecules due to their high hydrophobicity Aggregates naturally in biological media, thus this phenomenon becomes a major obstacle for practical application in the fields of bioimaging and therapeutics

Method used

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  • Aggregation-induced emission type near-infrared fluorescent material and synthesis method thereof
  • Aggregation-induced emission type near-infrared fluorescent material and synthesis method thereof
  • Aggregation-induced emission type near-infrared fluorescent material and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 1. 1.5mL (13.4mmol) m-aminoanisole, 8.76g (40.2mmol) 4-methyl iodobenzene, 7.5g (67mmol) potassium tert-butoxide, 483mg (2.68mmol) o-phenanthroline, 510mg ( 2.68mmol) cuprous iodide was added in 20mL toluene, stirred and reacted at 125°C for 20 hours, filtered and spin-dried the filtrate, dry column chromatography (the mixed solution of petroleum ether and ethyl acetate volume ratio of 100:1 was eluent), to obtain the compound of formula I.

[0047]

[0048] 2. Dissolve 1.74mL (18.4mmol) of boron tribromide in 18mL of dichloromethane, and add 3.72g (12.26mmol) of the compound of formula I in dichloromethane, and stir and react at room temperature for 12 hours. The reaction solution was poured into ice water, extracted with deionized water and dichloromethane, and a mixture of petroleum ether and ethyl acetate with a volume ratio of 30:1 was used as the eluent) to obtain the compound of formula II.

[0049]

[0050]3. Add 6.8mL (88.5mmol) N,N-dimethylformamide to ...

Embodiment 2

[0060] In this example, malononitrile in Example 1 was replaced with an equimolar amount of the compound of formula VI, and the other steps were the same as in Example 1 to obtain the fluorescent dye shown in V-2 with a yield of 75%.

[0061]

[0062] The structural characterization data of the resulting product are: 1 H NMR (300MHz, CDCl 3 )δ8.65(s,1H),7.71-7.55(m,5H),7.38(d,J=8.8Hz,1H),7.15(dd,J=27.4,8.2Hz,8H),6.93(s,1H ),6.82(dd,J=8.8,2.2Hz,1H),6.66(d,J=2.1Hz,1H),2.37(s,6H).

[0063] The formula VI compound used in the present embodiment is prepared according to the following method:

[0064] Add 1g (5mmol) of α-bromoacetophenone, 427mg (5mmol) of cyanoacetic acid, 201mg (5mmol) of sodium hydroxide, and 3.9mL of deionized water into 18mL of ethanol, and react under reflux for 1 hour, cool to precipitate a solid, and filter to obtain Compound of formula VI.

[0065]

Embodiment 3

[0067] In this example, malononitrile in Example 1 was replaced with an equimolar amount of the compound of formula VII, and other steps were the same as in Example 1 to obtain the fluorescent dye shown in V-3 with a yield of 67%.

[0068]

[0069] The structural characterization data of the resulting product are: 1 H NMR (300MHz, CDCl 3 )δ7.97-7.82(m,2H),7.43(d,J=16.1Hz,1H),7.32(d,J=8.9Hz,1H),7.16(dd,J=29.3,8.3Hz,8H), 6.82(dd,J=8.8,2.2Hz,1H),6.67(d,J=2.0Hz,1H),2.38(s,6H),1.72(s,6H).

[0070] The compound of formula VII used in this embodiment is prepared according to the following method:

[0071] Add 3.2mL (30mmol) of 3-hydroxy-3-methyl-2-butanone, 5.9g (90mmol) of malononitrile, and 3.8g (34mmol) of magnesium ethoxide into 30mL of ethanol, and react at 60°C for 8 hours. The reaction solution was spin-dried and then subjected to dry column chromatography (using a mixture of petroleum ether and ethyl acetate at a volume ratio of 20:1 as the eluent) to obtain the compoun...

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Abstract

The invention discloses an aggregation-induced emission type near-infrared fluorescent material and a synthesis method thereof. The structural formula of the fluorescent material is shown in the specification, wherein R represents items in the specification; the method includes obtaining 3-methoxy-4-(N, N-dimethylphenyl) aniline by reacting 4-methyl iodobenzene with m-aminoanisole; preparing 4-(xylyl amino) salicylaldehyde via demethylating and a Vilsmeier reaction, carrying out a Witting reaction to obtain an intermediate, carrying out a Vilsmeier reaction to obtain 7-(xylyl amino) coumarin-3-formaldehyde, and finally, carrying out a nucleophilic reaction to obtain the fluorescent material. The fluorescent material provided by the invention realizes aggregation-induced emission characteristics and near-infrared emission characteristics in an organic small molecular skeleton, and also has singlet oxygen generation characteristics. By utilizing the characteristics, the fluorescent material has a great application prospect in the aspects of bioluminescence imaging, bacteriostasis, sterilization and the like.

Description

technical field [0001] The invention belongs to the technical field of near-infrared aggregation-induced fluorescent materials, and specifically relates to a fluorescent material having aggregation-induced luminescent properties, near-infrared luminescent properties, and the property of generating singlet oxygen, and a preparation method of the material. Background technique [0002] Fluorescence bioimaging technology has become a powerful and non-invasive biological visualization analysis tool due to its advantages of fast response, high temporal resolution, high sensitivity, good field operability, simple operation, and good reproducibility. As the main branch of fluorescent materials, small-molecule organic fluorophores are currently in an explosive development stage, especially near-infrared emitting (>700nm) fluorophores, which have high penetration depth, low biological autofluorescence interference, and light damage to biological structures. Small, light scattering...

Claims

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Application Information

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IPC IPC(8): C07D311/16C07D405/06C07D407/06C09K11/06G01N21/64A61K41/00A61P31/04
CPCC07D311/16C07D405/06C07D407/06C09K11/06G01N21/6428A61K41/0057A61P31/04C09K2211/1088C09K2211/1029
Inventor 李楠赵娜李悦
Owner SHAANXI NORMAL UNIV
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