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Organic compound for preparing wide pH fluorescence probes and application thereof

A technology of organic compounds and fluorescent probes, which can be used in organic chemistry, organic dyes, pH testing, etc., and can solve the problems of easy damage, high impedance, and inability to measure a wide range of pH values.

Active Publication Date: 2015-02-11
FORLIGHTS DETECTION TECH LLC SUZHOU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of electrochemical sensor has many inherent defects: reference electrode is required, frequent calibration, high impedance, easy to break, "sodium error" in the case of high alkalinity, etc.
Fluorescent sensors based on the photoinduced electron transfer (PET) mechanism have been reported, but all reported fluorescent sensors are limited to the measurement of a narrow range of pH values ​​and do not have the ability to measure a wide range of pH values.

Method used

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  • Organic compound for preparing wide pH fluorescence probes and application thereof
  • Organic compound for preparing wide pH fluorescence probes and application thereof
  • Organic compound for preparing wide pH fluorescence probes and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Synthesis of Compound P12:

[0083] Phenylethylamine (P11) (60.5 g 0.50 mol) was mixed with concentrated hydrochloric acid (50 ml, 0.6 mol). The formed salt was dissolved in 65 ml of water. Slowly add this solution dropwise to 600ml of 35% nitric acid solution under rapid stirring at room temperature. Stirring was continued overnight after the dropwise addition was complete. The resulting yellow precipitate was filtered, dissolved in 300ml of water, and the pH was greater than 12 with 40% sodium hydroxide, extracted with dichloromethane (3x300ml), the resulting solution was dried with anhydrous potassium carbonate, filtered, and spin-dried to obtain 61.5g of the product (74%). 1H NMR (CDCl 3 ) δ = 2.80(t, 2H), 2.64(s, br, 2H), 2.94(t, 2H), 7.55(d, 2H), 8.25(d, 2H).

[0084] Synthesis of Compound P13:

[0085] Dissolve nitrophenethylamine (P12) (61.5g 0.37mol) in ethanol (400ml), add 3.3g of 5% palladium carbon, and carry out catalytic hydrogenation under normal pr...

Embodiment 2

[0093] Synthesis of Compound P25

[0094] Add compound P14 (2.0g, 3.83mmol), ethyl iodide (2.43g, 15.32mmol), potassium iodide (2.54g, 15.32mmol), DIEA 2.3mL (15.30mmol) and 12ml NMP in a 50ml single-necked bottle, 110°C Stir for 24 hours. After the reaction is complete, pour into 280ml of ice water. The resulting yellow precipitate was filtered and washed three times with 40 ml of water. The resulting crude product was purified by a silica gel column to obtain 1.83 g (83%) of a yellow solid. 1H NMR (300MHz, CDCl3): 1.55(s, 9H), 1.25(t, 6H), 3.53(q, 4H), 2.97(t, 2H), 3.35(t, 2H), 5.38(s, 2H), 6.68 (t, 2H), 7.56-7.55 (m, 3H) 7.85 (d, 2H) 8.05 (d, 2H) 8.40 (d, 2H) 8.60 (d, 2H).

[0095] Synthesis of compound P26: Weigh compound P25 (0.16g, 0.28mmol) into 4ml of dichloromethane, then add 2ml of trifluoroacetic acid, stir at room temperature for 30min, spin off the solvent to obtain 0.18g of a yellow solid, and proceed directly to the next step.

[0096] The synthesis of compo...

Embodiment 3

[0098] Synthesis of compound P52: slowly dissolve tyramine (10 g, 72.90 mmol) in THF (ie tetrahydrofuran, 140 ml) and methanol (20 ml), then add triethylamine (7.36 g, 72.90 mmol). The solution was cooled to 0°C with an ice-salt bath, and di-tert-butyl carbonate (8.20 g, 87.48 mmol) was added in batches. After the addition was complete, it was stirred at 0°C for 1 hour, then at room temperature overnight. The solvent was spin-dried to obtain 18.0 g (91%) of the product. 1 H NMR (300MHz, DMSO-d6): δ9.12(s, 1H), 6.96(d, J=8.1Hz, 2H), 6.78(t, J=5.1Hz, 1H), 6.66(d, J=8.4 Hz, 2H), 3.00-3.07(m, 2H), 2.54(t, J=7.8Hz, 2H), 1.35(s, 9H). 13 C NMR (DMSO-d6): δ156.256, 130.125, 130.102, 115.737, 78.108, 42.602, 35.426.28.934.

[0099] Synthesis of compound P32: Compound P52 (8.0 g, 33.71 mmol) was dissolved in 160 ml of anhydrous dichloromethane, and heated to reflux under nitrogen protection. Dissolve 13.65 g (101.41 mmol) of sulfonyl chloride in 100 ml of anhydrous dichloromethane a...

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Abstract

The invention discloses an organic compound for preparing wide pH fluorescence probes. The organic compound is capable of carrying out combination at any ratio according to the actual requirements and being fixed on a hydrophilic polymer to further detect the pH value of a water environment. According to the organic compound, continuous measurement on the pH value can be achieved; and the efficiency, the sensitivity and the repeatability are greatly improved.

Description

technical field [0001] The invention relates to the field of organic compounds capable of measuring acidity and alkalinity, in particular to an organic compound for preparing a wide range of pH fluorescent probes and applications thereof. Background technique [0002] Acidity and alkalinity (pH value) is one of the most important measurement parameters in various scientific researches and practical applications, so the development of sensors for measuring pH has also attracted much attention. Electrochemical sensors (pH glass electrodes) are currently the most widely used pH sensors. But this type of electrochemical sensor has many inherent defects: reference electrode is required, frequent calibration, high impedance, easy to break, "sodium error" in the case of high alkalinity, etc. Photochemical sensors, including fluorescence and absorption pH sensors, just make up for the deficiency of glass electrode pH sensors. However, the photochemical sensor also has its inherent...

Claims

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Application Information

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IPC IPC(8): C07D221/14C07D311/90C07D311/82C09K11/06G01N21/64
CPCC07D221/14C07D311/82C07D311/90C09K11/06C09K2211/1018G01N21/643G01N21/80C09B11/24C09B11/28C09B15/00C09B57/08G01N31/221
Inventor 何华瑞
Owner FORLIGHTS DETECTION TECH LLC SUZHOU
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