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Preparation method and use of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine

A technology of naphthoyl chloride and hydrazide, which is applied in the application field of chemical sensing technology, and can solve problems such as application limitations, poor selectivity, and susceptibility to interference

Inactive Publication Date: 2012-09-12
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are many indicators used to qualitatively or quantitatively detect the acidity of solutions. The disadvantages of these methods are mainly poor selectivity and easy interference, and their application is greatly limited.

Method used

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  • Preparation method and use of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine
  • Preparation method and use of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine
  • Preparation method and use of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Method 1 Synthesis of target compound I:

[0044] Add 1.00g (2.09 mmol) rhodamine B (in the form of hydrochloride) and 2 mL of phosphorus oxychloride into a 100 mL flask, reflux at 100°C for 2-10 hours, spot the plate to detect the progress, until the raw materials are completely reacted, Turn off heat. Yield: 81.3%. Alternatively, rhodamine B and excess hydrazine hydrate are refluxed in a polar solvent to prepare rhodamine B hydrazide. Add 0.50 g (2.62 mmol) of 1-naphthoyl chloride to 0.91 g (2.0 mmol) of rhodamine B hydrazide in tetrahydrofuran, add 8 mL of triethylamine, heat, reflux, and monitor the progress of the reaction by TLC. After 2-26 hours, the heating was stopped. After the reaction mixture was cooled, it was poured into an ice-water mixture, extracted with dichloromethane to obtain an organic phase, dried overnight with anhydrous magnesium sulfate, and spin-dried. The obtained crude product was purified by column chromatography using cyclohexane and et...

Embodiment 2

[0046] Method two synthetic target compound I:

[0047]Add 1.00 g (2.2 mmol) of rhodamine B acid chloride to a solution of 0.41 g (2.2 mmol) of 1-naphthoic hydrazide in tetrahydrofuran, add 8 mL of triethylamine, heat, reflux, and monitor the progress of the reaction by TLC. After 2-26 hours, the heating was stopped. After the reaction mixture was cooled, it was poured into an ice-water mixture, extracted with dichloromethane to obtain an organic phase, dried overnight with anhydrous magnesium sulfate, and spin-dried. The obtained crude product was purified by column chromatography using cyclohexane and ethyl acetate as developing solvents. Obtained 0.96 g of the target product as an off-white solid with a yield of 78.6%.

Embodiment 3

[0049] Response detection of compound I silica gel plate support sheet to volatile organic acid mist:

[0050] In order to explore the spectral properties of compound I and its response to acid mist, a silica gel plate with a size of 20 mm × 20 mm (coated plate thickness 0.2-0.25 mm) was prepared in CH with a concentration of 1.0 mg / 10 mL of compound I 2 Cl 2 Soak in the solution, then place in high vacuum, dark, and dry at room temperature for 24-48 hours. The fluorescence detection of acid vapor is carried out in a container with a volume of 100 mL. The silica gel plate loaded with compound I is placed in the center of the container, and then 10 microliters of different volatile organic acids are dripped into the bottom with a micro-syringe (the types of acids include : formic acid, acetic acid, and phosphorus oxychloride), take it out after 10 seconds, and compare the experimental silica gel plate with the blank silica gel plate, showing a change from light pink to deep pi...

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Abstract

The invention discloses a preparation method and a use of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine. N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine is shown in the structural formula I. A rhodamine dye is an excellent optical fluorescent probe matrix. The preparation method realizes the preparation of a double (rhodamine B) acylhydrazine derivative having a 1-naphthoyl substituent group and a spiro structure first. Under acidic conditions, the spiro structure of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine is transformed into an open state from a closed state and simultaneously, the change from an achromatic color to a pink color is produced in a molecular spectrum of N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine; and under the action of exciting light having a certain wavelength, N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine produces fluorescent light. After being adsorbed on a silica gel plate, N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine shown in the structural formula I can produce visible light and a fluorescent or chroma response under the action of volatile acid gas. N-(1-naphthoyl)-N'-[rhodamine B-9-(2-benzoyl)]hydrazine shown in the structural formula I can be used for naked eye chromogenic identification and fluorescent identification probes of acid mist.

Description

[0001] The present invention is carried out under the support of the Development Fund of Tianjin Normal University (the fund number is 52XK1102). technical field [0002] The invention belongs to the application field of chemical sensing technology and relates to N -(1-Naphthoyl)- N’ -[Rhodamine B-9-(2-benzoyl)]hydrazine compound I and its preparation method, and the use of I as an acidity detection probe, especially for the detection of volatile acidic gases. Background technique [0003] At present, there are many indicators used to qualitatively or quantitatively detect the acidity of solutions. The disadvantages of these methods are mainly poor selectivity and easy interference, and their applications are greatly restricted. Rhodamine B bishydrazide compounds have excellent light absorption and fluorescence characteristics. Rhodamine B is used as the parent to modify various characteristic groups in order to continuously improve the high selectivity and high sensitivity...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06C09B57/00G01N21/29G01N21/64
Inventor 史学芳李红郁马媛郭萍徐本花陈雯
Owner TIANJIN NORMAL UNIVERSITY
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