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Acid pH probe compound and production method thereof

A compound and acidic technology, applied in the field of fluorescent probes, can solve the problems of loss of structure and unsatisfactory stability, and achieve the effect of stable structure, difficult hydrolysis and good stability

Active Publication Date: 2019-06-07
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the inventors found that the above-mentioned Schiff base structure, as the main active site in the sensor material, is often unsatisfactory in stability under strong acid conditions. Most pH fluorescent probes respond to neutral pH in the range of 6-8, weak acid pH 4 to 6, few probes are sensitive to pH values ​​below 4, suitable for use in extremely acidic conditions
In addition, the Schiff base is more likely to be hydrolyzed in a liquid acidic environment, losing its original structure

Method used

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  • Acid pH probe compound and production method thereof
  • Acid pH probe compound and production method thereof
  • Acid pH probe compound and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Synthesis of acidic pH fluorescent probe.

[0045] The acidic pH fluorescent probe compound has the molecular structural formula as the aforementioned formula I.

[0046] The preparation method steps are as follows:

[0047] Dissolve 5-indole formaldehyde and 4-aminotriphenylamine in ethanol solvent, add two drops of glacial acetic acid, reflux at 60-70°C for 5-6h, cool to room temperature, filter with suction, wash with absolute ethanol, and dry to obtain pH probe compound. 1 H NMR (400MHz, DMSO) δ11.74(s,1H),8.72(s,1H),8.35(d,J=7.7Hz,1H),7.97(d,J=1.9Hz,1H),7.51–7.40 (m,1H),7.29(t,J=7.7Hz,4H),7.23–7.10(m,4H),7.02(t,J=9.3Hz,8H).

Embodiment 2

[0048] The preparation of embodiment 2 compound

[0049] a. Preparation of 4-nitrotriphenylamine

[0050] Slowly add triphenylamine and an appropriate amount of dichloromethane into a round bottom flask, slowly add concentrated nitric acid dropwise at 0°C, stir for 3 hours, remove dichloromethane by rotary evaporation, filter, wash with water, recrystallize with ethanol, and dry to obtain yellow solid. The molar ratio of triphenylamine to nitric acid is 1:3.

[0051] b. Preparation of 4-aminotriphenylamine

[0052] Dissolve 4-nitrotriphenylamine in ethanol solution, then add palladium carbon, and pass through hydrogen as a reducing agent. Then, react at 68°C for 6.5 hours, remove palladium carbon by filtration, remove ethanol by rotary evaporation, and remove palladium carbon by filtration. A certain amount of dichloromethane and methanol was selected for column chromatography, and the first point was collected to obtain a lavender solid with a yield of 61%.

[0053] The ...

Embodiment 3

[0057] The preparation of embodiment 3 compound

[0058] a. Preparation of 4-nitrotriphenylamine

[0059] Slowly add triphenylamine and an appropriate amount of dichloromethane into a round-bottomed flask, slowly add concentrated nitric acid dropwise at 0°C, stir for 2 hours, remove dichloromethane by rotary evaporation, filter, wash with water, recrystallize with ethanol, and dry to obtain yellow solid. The molar ratio of triphenylamine to nitric acid is 1:1.

[0060] b. Preparation of 4-aminotriphenylamine

[0061] Dissolve 4-nitrotriphenylamine in ethanol solution, then add palladium carbon, and pass through hydrogen as a reducing agent. Then, react at 60°C for 6 hours, remove palladium carbon by filtration, remove ethanol by rotary evaporation, and remove palladium carbon by filtration. A certain amount of dichloromethane and methanol was selected for column chromatography, and the first point was collected to obtain a lavender solid with a yield of 58%.

[0062] The ...

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Abstract

The invention relates to the technical field of fluorescence probes, in particular to an acid pH probe compound and a production method thereof. Triphenylamine compounds can be used as induced luminescence materials due to good fluorescence performance, and a schiff base structure has good coordination capability and protonation capability so that triphenylamine schiff base fluorescence compoundscan be used as pH sensing materials excellent in performance. However, the stability, especially in an acid water environment, of the schiff base structure under an acid condition is not ideal, and hydrolysis is prone to happen so that most of the schiff base structure pH probe compounds can hardly adapt to detection under strong acid water body conditions. The invention provides the acid pH fluorescence probe compound novel in structure; and the acid pH probe compound novel in structure has a good response effect in a pH range of 2-7, can adapt to strong acid water body environments, and hasimportant significance when applied for water body detection.

Description

technical field [0001] The disclosure relates to the technical field of fluorescent probes, in particular to a pH probe compound suitable for strong acidic environments and a preparation method thereof. Background technique [0002] The information disclosed in this Background section is only intended to increase the understanding of the general background of the disclosure, and is not necessarily to be taken as an acknowledgment or any form of suggestion that the information constitutes prior art that is already known to those skilled in the art. [0003] Triphenylamine and its derivatives have relatively high hole mobility and good fluorescence properties, and are widely used in the construction of branched groups in multi-dendritic optoelectronic materials and the formation of rotation units in aggregation-induced luminescent materials. On the other hand, due to the lone pair of C=N electrons, Schiff base compounds have good coordination ability and protonation ability, a...

Claims

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Application Information

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IPC IPC(8): C07D209/08C09K11/06G01N21/64
Inventor 张献高志岩朱华杰刘伟良姚金水
Owner QILU UNIV OF TECH
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