Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof

A technology of benzimidazole and fluorescent probes, applied in fluorescence/phosphorescence, organic chemical methods, chemical instruments and methods, etc., can solve the problems of high professionalism in operation and strict detection environment

Active Publication Date: 2020-09-18
NANJING FORESTRY UNIV
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  • Description
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  • Application Information

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Problems solved by technology

Although there are many detection methods for metal ions, such as atomic absorption method, spectrophotometry, cyclic voltammetry, etc., these methods have problems such as strict detection environment, high sample standard requirements, and high professionalism in operation. The advantages of fast detection speed, wide detection environment and high sensitivity have been applied to the detection of iron ions, mercury ions and other metal ions
In recent years, people have studied many organic fluorescent probes for the detection of metal ions, such as rhodamine-based fluorescent probes to detect ferric ions, naphthylamide-based fluorescent probes to detect ferric ions, and coumarin-based fluorescent probes to detect ferric ions. Detect iron ions, mercury ions, etc., but there is no report on the synthesis of dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probes to detect iron ions and mercury ions

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  • Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof
  • Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof
  • Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthetic method of dehydroabietic acid base 2,4-diarylbenzimidazole compound, the synthetic process is:

[0032]

[0033] Specific steps are as follows:

[0034] 1) Preparation of 12-bromo-13,14-dinitrodehydroabietic acid methyl ester: dehydroabietic acid is prepared through methyl esterification, bromination and double nitration reactions. The specific process is as follows:

[0035] Weigh 30g of dehydroabietic acid and dissolve it in 60mL of toluene, add 11mL of thionyl chloride and react at 78-80°C for 3h, spin dry under vacuum, add 60mL of methanol, react at 78-80°C for 3h, spin dry and add 30mL of ethanol was dissolved to obtain methyl dehydroabietate;

[0036] Accurately weigh 5g of methyl dehydroabietate, dissolve it in 30mL of acetonitrile, add 4g of N-bromosuccinimide, and react at room temperature in the dark for 24 hours, rotary steam, wash twice with dichloromethane, dissolve crystals in 100mL of methanol, Obtain 12-bromodehydroabietic acid methyl ...

Embodiment 2

[0046] 2-(2-Hydroxynaphthalen-1-yl)-6,9a-dimethyl-11-(3,4,5-methoxyphenyl-4,5,5a,6,7,8,9 ,9a-octahydro-3H-phenanthro[1,2-d]imidazole-6-methyl ester was dissolved in aqueous ethanol (ethanol:water=1:1) (1×10 -5 M), add (0-1)×10 -4 Fe of M 3+ , Hg 2+ Different concentrations of Fe were measured 3+ , Hg 2+ p-2-(2-Hydroxynaphthalen-1-yl)-6,9a-dimethyl-11-(3,4,5-methoxyphenyl-4,5,5a,6,7,8,9 , the fluorescence absorption spectrum of 9a-octahydro-3H-phenanthro[1,2-d]imidazole-6-methyl ester, such as figure 11a: the fluorescence absorption spectrum of the addition of iron ions; 1b: the fluorescence absorption spectrum of the addition of mercury ions, the fluorescence absorption of the compound is obviously weakened until it is quenched, indicating that the compound can interact with Fe 3+ , Hg 2+ Complexation.

Embodiment 3

[0048] Accurately weigh 62mg of 2-(2-hydroxynaphthalen-1-yl)-6,9a-dimethyl-11-(3,4,5-methoxyphenyl-4,5,5a,6,7, 8,9,9a-Octahydro-3H-phenanthro[1,2-d]imidazole-6-methyl ester was dissolved in 10mL of absolute ethanol to prepare 1×10 -3 M solution, take 100 μM stock solution and dilute it with ethanol aqueous solution (ethanol:water=1:1) to 10mL with a concentration of 1×10 -5 M solution, 5 μL of Fe was added each time 3+ (1×10 -2 M), Hg 2+ (1×10 -2 M), with Fe 3+ The added solution turns pale yellow, with the increase of Hg 2+ The color of the added solution did not change. Observed under 365nm ultraviolet light, such as figure 2 As shown, 2a: the compound added Fe under sunlight 3+ , Hg 2+ Photos before and after ions; 2b: Fe added to the compound under 365nm UV light 3+ , Hg 2+ Ion before and after photos with Hg added 2+ , Fe 3+ The blue fluorescence of the solution of ions is quenched, indicating that the compound is compatible with Hg 2+ , Fe 3+ Complexation...

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Abstract

The invention discloses a dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and a preparation method and application thereof. The preparation methodcomprises the following steps: subjecting dehydroabietic acid to acylating chlorination and methyl esterification to synthesize methyl dehydroabietate; subjecting a product obtained after reacting methyl dehydroabietate with NBS to double nitrification so as to synthesize methyl 12-bromo-13,14-dinitrodehydroabietate; reacting methyl 12-bromo-13,14-dinitrodehydroabietate with 3,4,5-trimethoxyphenylboronic acid to generate methyl 12-(3,4,5-trimethoxyphenyl)-13,14-dinitrodehydroabietate; performing a Fe/HCl reduction reaction to generate methyl 12-(3,4,5-trimethoxyphenyl)-13,14-diaminodehydroabietate; and condensing the methyl 12-(3,4,5-trimethoxyphenyl)-13,14-diaminodehydroabietate with 2-hydroxy-1-naphthaldehyde to obtain a desired compound. The compound can selectively react with Fe<3+> and Hg<2+> to generate a complex, blue fluorescence is quenched after the complex is formed, and the compound can be used as the fluorescent probe for detecting the concentration of Fe<3+> or Hg <2+>.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and specifically relates to a dehydroabietic acid-based 2,4-diarylbenzimidazole type ferric ion, a mercury ion fluorescent probe, a preparation method and application thereof. Background technique [0002] Fe 3+ As one of the essential trace elements for the human body, iron plays a vital role in biological and pathological processes, participating in oxidation reactions and enzymatic reactions. Excess or deficiency of iron ions can cause different diseases, such as cancer, anemia, Alzheimer's disease, Parkinson's, etc. Mercury is a toxic element and in all its forms is a potential health hazard as it can accumulate in vital organs such as the brain and kidneys and cause untreatable disease. Although there are many detection methods for metal ions, such as atomic absorption method, spectrophotometry, cyclic voltammetry, etc., these methods have problems such as strict detection e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07J73/00C09K11/06G01N21/64
CPCC07D235/02C07J73/008C09K11/06G01N21/6428C07B2200/07C09K2211/1044C09K2211/1011
Inventor 谷文李阿良王忠龙王文燕刘青松孙月王石发
Owner NANJING FORESTRY UNIV
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