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Application of polyether modified organosilicon copolymer in enhancing fluorescence detection performance of lipophilic AIE organic fluorescence probe

A fluorescent probe and polyether modification technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of disordered aggregation, non-uniform dispersion, and fluorescence quenching of fluorescent probe molecules, and achieve improved water solubility. Performance and detection sensitivity, large acid and alkali tolerance, and the effect of improving fluorescence intensity

Active Publication Date: 2022-06-17
SOUTHEAST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as a dynamic organelle, lipid droplets mainly exist in the water-soluble cytoplasm and other organelles. Therefore, the lipid-soluble AIE organic fluorescent probe molecules targeting lipid droplets have great potential in practical biological applications, especially in biosensing and During detection, there are phenomena such as poor water solubility and adsorption of solute molecules or particles due to lipophilicity and hydrophobicity, which cause problems such as disordered aggregation, non-uniform dispersion and fluorescence quenching of fluorescent probe molecules in biosensing and detection media, which are serious. The practical application of fat-soluble AIE organic fluorescent probe molecules targeting lipid droplets is restricted

Method used

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  • Application of polyether modified organosilicon copolymer in enhancing fluorescence detection performance of lipophilic AIE organic fluorescence probe
  • Application of polyether modified organosilicon copolymer in enhancing fluorescence detection performance of lipophilic AIE organic fluorescence probe
  • Application of polyether modified organosilicon copolymer in enhancing fluorescence detection performance of lipophilic AIE organic fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～2

[0047] Preparation of hydrogen-containing silicone oil: equipped with thermometer, stirrer, reflux condenser (equipped with N 2 Into the 100mL three-necked bottle of trachea), add 202 silicone oil (H%=1.55%) 10.0g, hexamethyldisiloxane 1.95g, octamethylcyclotetrasiloxane 52.0g, and the amount of concentrated sulfuric acid catalyst is the total amount of material. 1% of the mass, the reaction temperature is 85 ° C, the reaction is carried out for 8 hours, and the hydrogen-containing silicone oil intermediate of Example 1 is synthesized by telomerization reaction; 1.95g of hexamethyldisiloxane is adjusted to 4.55g, and other synthesis conditions remain unchanged, the synthesis example 2 Hydrogenated silicone oil intermediate.

[0048] Preparation of polyether modified organosilicon copolymer: equipped with thermometer, stirrer, reflux condenser (equipped with N 2 In the 100mL there-necked flask of the trachea), hydrogen-containing silicone oil and allyl polyether were added to ...

Embodiment 3

[0053] Preparation of AIE organic fluorescent probe TTI:

[0054] (1) 1 mmol a (4-bromo-N,N-diphenylaniline) and 1 mmol b ((5-formylthiophen-2-yl)boronic acid) were dissolved in 20 mL of a mixed solvent of methanol and toluene (methanol The volume ratio of toluene and toluene is 1:1), and potassium carbonate (5mmol) is added to it, and after stirring evenly, the air in the reaction system is removed and 1,1'-bisdiphenylphosphinoferrocene dichloride is added thereto. Palladium (0.1 mmol) was removed and the reaction temperature was raised to 85°C after further removal of air and the reaction was continued for 12 hours. After the reaction was completed, the solvent was removed, and the mixture was eluted with a mixed liquid of petroleum ether:ethyl acetate=100:1 to obtain a yellow solid product c(5-(4-(diphenylamino)phenyl)thiophene- 2-formaldehyde); product c 1 H NMR (600MHz, CDCl 3 )δ9.86(s,1H),7.71(d,J=4.0Hz,1H),7.54-7.51(m,2H),7.32-7.29(m,5H),7.15(dd,J=8.5,0.9Hz , 4H), 7...

Embodiment 4

[0057] Preparation of AIE organic fluorescent probe TOI: on the basis of Example 3, replace b((5-formylthiophen-2-yl)boronic acid) with (5-formylfuran-2-yl)boronic acid, other conditions constant.

[0058] of product c (5-(4-(diphenylamino)phenyl)furan-2-carbaldehyde) 1 H NMR (600MHz, CDCl 3 )δ9.59(s,1H),7.65(d,J=8.8Hz,2H),7.31–7.29(m,4H),7.28(s,1H),7.13(d,J=7.7Hz,4H), 7.08 (dd, J=16.6, 8.1 Hz, 4H), 6.70 (d, J=3.7 Hz, 1H).

[0059] TOI is a brown-green solid, 1H NMR(600MHz, CDCl3)δ7.95-7.92(m,2H),7.77-7.72(m,3H),7.70(d,J=8.6Hz,2H),7.33-7.29(m , 4H), 7.15 (dd, J=8.5, 1.0 Hz, 4H), 7.14–7.05 (m, 5H), 6.88 (d, J=3.8 Hz, 1H).

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Abstract

The invention discloses an application of a polyether modified organic silicon copolymer in enhancing the fluorescence detection performance of a lipophilic AIE organic fluorescent probe. The polyether modified organic silicon copolymer and a fluorescent probe molecule interact with each other, so that the fluorescence detection performance of the lipophilic AIE organic fluorescent probe is enhanced. Nano particles with fluorescent probe molecules inside and polyether modified organic silicon copolymer wound outside are formed through self-assembly, so that the fluorescence detection performance of the lipophilic AIE organic fluorescent probe is enhanced; the water solubility and detection sensitivity of the lipophilic AIE organic fluorescent probe are effectively improved, and the detection condition is endowed with large acid and alkali tolerance.

Description

technical field [0001] The invention relates to the application of an organosilicon copolymer, in particular to the application of a polyether-modified organosilicon copolymer in enhancing the fluorescence detection performance of a lipophilic AIE organic fluorescent probe. Background technique [0002] Fluorescent molecules or fluorophores with Aggregation-Induced Emission (AIE) have a wide range of applications in biosensing and imaging and stimulus-response systems, such as online monitoring of biological processes, in vivo-specific fluorescence imaging, biological Small molecule fluorescence detection and sensing, biological stimulus response systems, gene transfection and drug delivery, and in vivo photodynamic therapy, etc. At present, AIE organic fluorescent probes for cell membrane, endoplasmic reticulum, mitochondria, lipid droplets, lysosomes and nucleus have been reported in the literature. [0003] As an important dynamic organelle, lipid droplets are formed in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/02C09K11/06C08G77/46G01N21/64
CPCC09K11/025C09K11/06G01N21/6428C08G77/46C09K2211/1007C09K2211/1014C09K2211/1092C09K2211/1011C09K2211/1088
Inventor 祁争健张冬冬王省代艳鹏薛珂梁健康赵鑫鑫
Owner SOUTHEAST UNIV
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