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Fluorescent small-molecular probes based on single benzene ring and synthesis method thereof

A technology of small molecule probes and synthesis methods, applied in the field of fluorescent small molecule probes and their synthesis, can solve the problems of no fluorescence, destroying fluorescence behavior, etc., and achieve a wide range of solvent applications, good photochemical stability, and high fluorescence quantum yield. rate effect

Inactive Publication Date: 2020-01-17
XI'AN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The essence of the high fluorescence quantum yield of this type of compound is the presence of strong hydrogen bonds in and between molecules. However, its spectral properties hardly change with the polarity of the solvent, and if it is further derivatized, it will definitely Severely disrupts its fluorescent behavior or even renders it non-fluorescent

Method used

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  • Fluorescent small-molecular probes based on single benzene ring and synthesis method thereof
  • Fluorescent small-molecular probes based on single benzene ring and synthesis method thereof
  • Fluorescent small-molecular probes based on single benzene ring and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]Weigh ethyl 4-bromobenzoate, RuPhos-G3-Palladacycle, 2-dicyclohexylphosphine-2′,6′-diisopropoxy-1,1′-biphenyl (RuPhos) and Place cesium carbonate in a two-necked bottle, connect it to a double-row tube system to ensure a nitrogen atmosphere, dissolve the reactant with dry 1,4-dioxane, inject azetidine, and heat to reflux for 12- After 18 hours, the reaction was filtered, concentrated, and column separation was performed with dichloromethane:petroleum ether=1:5 to obtain the compound 4-azetidinylbenzoic acid ethyl ester. Among them, the molar ratio of ethyl 4-bromobenzoate, RuPhos-G3-Palladacycle, RuPhos, cesium carbonate and azetidine is 1:0.1:0.1:1:1.5.

[0077] The proton nuclear magnetic spectrum data of compound 1 (4-azetidinylbenzoic acid ethyl ester) is: 1 H NMR (600MHz, C 6 D. 6 )δ(ppm)8.27(m,2H),6.12(d,J=8.4Hz,2H),4.23(m,2H),3.30(m,4H),1.64(m,2H),1.09(t,J =7.2Hz, 3H).

[0078] see figure 1 , figure 1 Fluorescence emission spectra of the compound 4-azetidin...

Embodiment 2

[0080] Weigh ethyl 2-bromobenzoate, RuPhos-G3-Palladacycle, 2-dicyclohexylphosphine-2′,6′-diisopropoxy-1,1′-biphenyl (RuPhos) and Place cesium carbonate in a two-necked bottle, connect it to a double-row tube system to ensure a nitrogen atmosphere, dissolve the reactant with dry 1,4-dioxane, inject azetidine, and heat to reflux for 12- After 18 hours, the reaction was filtered, concentrated, and column separation was performed with dichloromethane:petroleum ether=1:3 to obtain the syrupy compound ethyl 2-azetidinylbenzoate. Among them, the molar ratio of ethyl 2-bromobenzoate, RuPhos-G3-Palladacycle, RuPhos, cesium carbonate and azetidine is 1:0.1:0.1:1:1.5.

[0081] The proton nuclear magnetic spectrum data of compound 2 (2-azetidinylbenzoic acid ethyl ester) are: 1 H NMR (600MHz, C 6 D. 6 )δ (ppm) 7.86 (d, J = 7.2Hz, 1H), 7.14 (m, 1H), 6.64 (t, J = 7.8, 15.0Hz, 1H), 6.26 (m, 1H), 4.13 (q, J =6.6Hz, 2H), 3.61(m, 4H), 1.71(m, 2H), 1.06(t, J=6.6, 13.8Hz).

[0082] see fi...

Embodiment 3

[0084] Weigh 2,5-dibromoethyl terephthalate, RuPhos-G3-Palladacycle, 2-dicyclohexylphosphine-2′,6′-diisopropoxy-1,1′-linked Benzene (RuPhos) and cesium carbonate are placed in a two-necked bottle, connected to a double-row tube system to ensure a nitrogen atmosphere, dissolved with dry 1,4-dioxane, and then injected with azetidine, heated to reflux After 12 to 18 hours, after the reaction, filter and concentrate, and conduct column separation with dichloromethane:petroleum ether=1:1 to obtain ethyl 2-azetidinyl-5-bromoterephthalate. Among them, the molar ratio of 2,5-dibromoethyl terephthalate, RuPhos-G3-Palladacycle, RuPhos, cesium carbonate and azetidine is 1:0.1:0.1:1.5:2.

[0085] Under the protection of argon, weigh ethyl 2-azetidinyl-5-bromoterephthalate, dissolve it in analytically pure methanol, add cuprous chloride and sodium borohydride in sequence, and stir at room temperature for 1-3 hours. The reaction mixture was filtered and concentrated, and column separation ...

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Abstract

The invention discloses fluorescent small-molecular probes based on a single benzene ring and a synthesis method thereof, belonging to the technical field of synthesis of small-molecular fluorescent probes. The fluorescent small-molecular probes use a single benzene ring as a basic structure and use azetidine and an alkoxycarbonyl group as an electron donor and an electron acceptor respectively; aseries of single-benzene-ring fluorescent small molecules are designed and synthesized by regulating and controlling the relative positions and numbers of two substituent groups on benzene rings, andare a series of single-benzene-ring small-molecular fluorescent probes with a wide solvent application range and flexibly adjustable fluorescent colors; the probes can show different solvatochromic behaviors based on an electronic push-pull structure; and the active reaction group, i.e., an ethoxycarbonylacyl group is introduced, so subsequent further derivation of the probes in practical application is facilitated.

Description

technical field [0001] The invention belongs to the technical field of synthesis of small-molecule fluorescent probes, and relates to a class of fluorescent small-molecule probes based on a single benzene ring and a synthesis method thereof. Background technique [0002] Due to the advantages of flexible and adjustable structure, wide spectral coverage and high fluorescence quantum efficiency, fluorescent molecular probes have attracted much attention in the fields of environmental monitoring, biosensing, and organic optoelectronic materials. According to the structural characteristics, it is mainly divided into two categories: one is the π-π conjugated system containing multiple aromatic rings or fused rings, and the other is the relatively small π-conjugated segment with electron donors and electron acceptors. Bulk push-pull fluorescent compounds. The former has a larger rigid framework, which is often underperformed in many aspects, such as poor solubility, strong π-π st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D205/04C09K9/02
CPCC07D205/04C09K9/02C09K2211/1007C09K2211/1029
Inventor 刘慧景
Owner XI'AN POLYTECHNIC UNIVERSITY
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