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Phenanthroimidazole-isoquinoline, derivative, preparation method and application thereof

A technology of imidazoles and compounds, applied in the field of catalytic synthesis of fine chemical products, achieving the effect of wide application prospects

Active Publication Date: 2014-04-30
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, alkynes are relatively inert relative to recent disulfide reagents or metal reagents, and it is difficult to react with relatively inert carbon-hydrogen bonds and nitrogen-hydrogen bonds on phenanthrene imidazoles

Method used

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  • Phenanthroimidazole-isoquinoline, derivative, preparation method and application thereof
  • Phenanthroimidazole-isoquinoline, derivative, preparation method and application thereof
  • Phenanthroimidazole-isoquinoline, derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Sequentially weigh 147.2mg of compound 2-phenylphenanthroimidazole represented by formula II (0.5mmol), 124.8mg of compound toluene shown in formula III (0.7mmol), 7.7mg of catalyst [Cp*RhCl 2 ] 2 (2.5% of the molar dosage of the compound represented by formula II) and 220.0 mg of oxidant copper acetate monohydrate (1.1 mmol) were placed in a 25 mL sealed tube containing a magnetic stirrer, and 5 mL of acetone was added. After sealing the sealed tube, put it into an oil bath at 120° C. and stir for 12 hours to perform a cyclization reaction based on carbon-hydrogen bond activation. After the reaction was completed, column separation was performed using petroleum ether-acetone as the eluent to obtain 194.5 mg of a light yellow solid, and the isolated yield of the target product 5,6-diphenylphenanthroimidazoisoquinoline was 83%.

[0053] figure 1 It is the crystal structure diagram of the product obtained in this example, and the structure of the compound can be seen fr...

Embodiment 2

[0055] Weigh in turn 175.2mg of compound 2-(p-tert-butylphenyl)phenanthroimidazole (0.5mmol), 124.8mg of tolanylacetylene (0.7mmol), 7.7mg of [Cp*RhCl 2 ] 2 (2.5% of the molar dosage of the compound represented by formula II) and 220.0 mg of copper acetate monohydrate (1.1 mmol) were placed in a 25 mL sealed tube containing a magnetic stirrer, and 5 mL of acetone was added. After sealing the sealed tube, put it into an oil bath at 120° C. and stir for 12 hours to perform a cyclization reaction based on carbon-hydrogen bond activation. After the reaction, use petroleum ether-acetone as the eluent to carry out column separation to obtain 242.7 mg of off-white solid, and the isolated yield of the target product 3-tert-butyl-5,6-diphenylphenanthroimidazoisoquinoline is 92%.

[0056] figure 2 and image 3 The proton nuclear magnetic resonance spectrum and carbon spectrum of the product prepared in this embodiment are respectively, and the structure of the compound can be seen ...

Embodiment 3

[0058] Sequentially weigh 162.2mg of compound 2-(p-methoxyphenyl)phenanthroimidazole (0.5mmol), 124.8mg toluene (0.7mmol), 7.7mg [Cp*RhCl 2 ] 2 (2.5% of the molar dosage of the compound represented by formula II) and 220.0 mg of copper acetate monohydrate (1.1 mmol) were placed in a 25 mL sealed tube containing a magnetic stirrer, and 5 mL of acetone was added. After sealing the sealed tube, put it into an oil bath at 120° C. and stir for 12 hours to perform a cyclization reaction based on carbon-hydrogen bond activation. After the reaction, use petroleum ether-acetone as eluent to carry out column separation to obtain 104.6 mg of a light yellow solid, and the isolated yield of the target product 3-methoxy-5,6-diphenylphenanthroimidazoisoquinoline is 42%.

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Abstract

The invention discloses a phenanthroimidazole-isoquinoline, a derivative, a preparation method and the application thereof. The structural formulas of the phenanthroimidazole-isoquinoline and the derivative thereof are shown as a formula I. The preparation method comprises the following steps: taking 2-aryl-phenanthroimidazole shown in a formula II and internal alkynes shown in a formula III as oligomers, performing carbon-hydrogen bond activation and cyclization reactions under certain solvents and a temperature under the existence of trivalent rhodium or bivalent ruthenium catalysts and oxidizing agents, and obtaining the phenanthroimidazole-isoquinoline when Ar is substituted phenyl or substituted benzene rings. The method is convenient, universal and economic. The formula I has wide application prospects in organic optoelectronic materials and the analysis field based on fluorescent detection and has selective fuorescent responsiveness especially for ferric irons. Therefore, the formula I can be used for ferric iron detection.

Description

technical field [0001] The invention belongs to the field of catalytic synthesis of fine chemical products, and relates to a phenanthroimidazoisoquinoline and derivatives thereof, a preparation method and application thereof. Background technique [0002] Phenanthroimidazole (1H-phenanthro[9,10-d]imidazole, referred to as phenanthroimidazole) is a rigid, conjugated heterocyclic skeleton, which consists of an imidazole ring and a phenanthrene ring by sharing two carbon atoms and a carbon-carbon double formed by keys. The conjugation between the two nitrogen atoms of imidazole and phenanthrene endows phenanthroimidazole with good electron injection and transport properties. At the same time, phenanthroimidazole derivatives have good thermal and electrochemical stability, making them ideal for organic semiconductor design. and a useful building block in synthesis. [0003] In recent years, phenanthroimidazole derivatives, as a novel organic semiconductor, have been widely use...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D495/14C09K11/06G01N21/64
CPCC07D471/04C07D495/14C09K11/06C09K2211/1044C09K2211/1051G01N21/643
Inventor 华瑞茂郑李垚
Owner TSINGHUA UNIV
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