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Porphyrin-crown ether compound, its synthesis and application

A technology of compound and crown ether, which is applied in the field of environmental analysis and biomedical research, can solve problems such as complex shape, large volume, and various forms, and achieve the effect of promoting solubility

Inactive Publication Date: 2012-04-11
WUHAN SYNCHALLENGE UNIPHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the inherent characteristics of anions, such as large size, complex shape, and various forms of existence, the design of their recognition molecules is extremely challenging.

Method used

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  • Porphyrin-crown ether compound, its synthesis and application
  • Porphyrin-crown ether compound, its synthesis and application
  • Porphyrin-crown ether compound, its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of a zinc porphyrin-crown ether (diaza 15-crown-5) compound as an inorganic anion sensor

[0032] Step 1: Add n-octane bromide (20.7 g, 0.10 mol) to 4-carboxybenzaldehyde (15.0 g, 0.10 mol) and anhydrous K 2 CO 3 (13.8 g, 0.10 mol) in 200 mL of DMF, heated to 80°C and stirred overnight. Cool, add ethyl acetate solvent, wash with dilute KOH solution, water and saturated brine successively, anhydrous Na 2 SO 4 dry. It was filtered, concentrated, and purified by column chromatography (petroleum ether / ethyl acetate, 25:1) to obtain a white solid (23.6 g, 90%). 1 H NMR (300 M, CDCl 3 ): d 0.86 (t, J = 6.64 Hz, 3 H), 1.28-1.46 (m, 10 H), 1.73-1.84 (m, 2 H), 4.35 (t, J = 6.68 Hz, 2 H), 7.95 (d, J = 8.10 Hz, 2 H), 8.19 (d, J = 8.10 Hz, 2 H), 10.10 (s, 1 H).

[0033] The second step: the product of the first step (8.70 g, 33.2 mmol) and pyrrole (23 ml, 10 equiv.) in 250 mL toluene solution was protected with nitrogen for 30 min, and then 1 mL of p-tol...

Embodiment 2

[0036] Example 2: Synthesis of a zinc porphyrin-crown ether (diaza 18-crown-6) compound as an inorganic anion sensor

[0037] Step 1: Add n-heptane bromide (19.3 g, 0.10 mol) to 4-carboxybenzaldehyde (15.0 g, 0.10 mol) and anhydrous K 2 CO 3 (13.8 g, 0.10 mol) in 200 mL of DMF, heated to 80°C and stirred overnight. Cool, add ethyl acetate solvent, wash with dilute KOH solution, water and saturated brine successively, anhydrous Na 2 SO 4 dry. It was filtered, concentrated, and purified by column chromatography (petroleum ether / ethyl acetate, 25:1) to obtain a white solid (22.1 g, 90%). 1 H NMR (300 M, CDCl 3 ): d 0.86 (t, J = 6.64 Hz, 3 H), 1.28-1.46 (m, 10 H), 1.73-1.84 (m, 2 H), 4.35 (t, J = 6.68 Hz, 2 H), 7.95 (d, J = 8.10 Hz, 2 H), 8.19 (d, J = 8.10 Hz, 2 H), 10.10 (s, 1 H).

[0038] The second step: the product of the first step (7.58 g, 33.2 mmol) and pyrrole (23 ml, 10 equiv.) in 250 mL of toluene solution was protected by nitrogen for 30 min, and then 1 mL of ...

Embodiment 3

[0041] Example 3: Referring to Example 1, the corresponding zinc porphyrin-crown ether compound can be obtained only by replacing brominated n-octane with C1-C7, C9 or C10 brominated n-alkanes or brominated benzyl. Likewise, magnesium, nickel or manganese porphyrin-crown ethers can be obtained by substituting magnesium acetate, nickel acetate or manganese acetate for zinc acetate.

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Abstract

The invention discloses a porphyrin-crown ether compound, which comprises a metallic porphyrin molecular skeleton and a crown ether complexation unit, as well as a linker connecting the two fragments in series. The compound has a general formula of: [Metallic porphyrin]-Linker-[Crown ether], the Metallic porphyrin represents metallic porphyrin, the Crown ether represents crown ether, and the Linker is an alkyl bond or an amide bond. In the invention, a metal ion on porphyrin can coordinate with different anions and cause optical signal changes of ultraviolet and fluorescence of a porphyrin chromophore, while the crown ether undergoes complexation with a counter cation (like Na<+>, K<+>, NH4<+>, etc.), preferably with a cation matching with the crown ether in size. For anions of different stereo configurations, the size of an intramolecular hole can be controlled by adjusting the length of a linking unit so as to make the intramolecular hole matching with an anion mutually. The obtained sensor molecule can detect inorganic anions with a concentration low to 0.1ppm (like C1<->, I<->, CN<->, SCN<->, and ClO4<->, etc.) in a water phase medium. The detection technology of high sensitivity in the invention is of great significance in environment analysis, biomedicine and other aspects.

Description

[0001] technical field [0002] The invention relates to a porphyrin-crown ether compound capable of selectively recognizing inorganic anions in an aqueous medium, provides an effective synthesis method thereof and an application in the field of anion detection, and belongs to the fields of environmental analysis and biomedicine research. Background technique [0003] Anions widely exist in living systems and natural environments, and play an important role in life sciences, environmental sciences, and medicinal chemistry. The substrates and coenzymes of most enzymes are anions, such as phosphate in ATP and ADP. Chloride ion is the main extracellular anion, and its ion channel is thought to be closely related to gallbladder fibrosis. At the same time, the effects of anions on environmental pollution and their impact on human health have now been realized. NO used in large quantities in industry 2 - and CN - After being degraded, it flows into rivers and lakes and infilt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/22G01N21/77
Inventor 刘慧黎占亭刘志平张淑娴
Owner WUHAN SYNCHALLENGE UNIPHARM INC
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