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A fluorescent probe for detecting water content in organic solvents and its preparation method and application

A technology of fluorescent probes and organic solvents, applied in the field of fluorescent probes for detecting water content in organic solvents and its preparation, achieving the effect of simple preparation methods

Active Publication Date: 2021-04-06
CHINA UNIV OF MINING & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Most of the fluorescent probes for detecting water reported in the current literature are based on the above mechanisms, and based on the joint action of twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) mechanisms to achieve the detection of water. relatively few reports

Method used

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  • A fluorescent probe for detecting water content in organic solvents and its preparation method and application
  • A fluorescent probe for detecting water content in organic solvents and its preparation method and application
  • A fluorescent probe for detecting water content in organic solvents and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: Probe compound TPEB-m-NO 2 Synthesis

[0042] 1) Synthesis of Compound 1

[0043] Into in a mixture of tetrahydrofuran (60 mL) / water (10 mL). Under a nitrogen atmosphere, the mixture was stirred at 80°C for 24 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. Purification by silica gel column chromatography (eluent: dichloromethane / n-hexane=1:3, V / V) gave compound 1. Yield: 52.8%. 1 H NMR (600MHz, CDCl 3 )δ8.53 (s,1H),8.37–8.29(m,2H),8.01(t,J=8.9Hz,1H),7.75(t,J=8.3Hz,1H),7.71(t,J=5.7 Hz, 1H). 13 C NMR (150MHz, CDCl 3 )δ 135.06, 132.17, 129.73, 124.06, 123.38, 77.25, 77.04, 76.83. Calculated exact mass: m / z 334.936, MALDI TOF-MS: m / z 334.932[M] + .

[0044] 2) Compound TPEB-m-NO 2 Synthesis

[0045] 1mmol compound 1, 1.1mmol 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylethenyl)phenyl)-1,3,2-dioxa Borolane, 0.05 mmol tetrakistriphenylphosphine palladium and 2 mmol potassium carbonate were added to a mixtu...

Embodiment 2

[0046] Embodiment 2: Probe compound TPEB-p-NO 2 Synthesis

[0047] 1) Synthesis of Compound 2

[0048] Into In a mixture of tetrahydrofuran / water (60 / 10). Under a nitrogen atmosphere, the mixture was stirred at 80°C for 24 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. Purification by silica gel column chromatography (eluent: dichloromethane / n-hexane=1:3, V / V) gave compound 2. Yield: 49.6%. 1 H NMR (600MHz, DMSO) δ8.41(d, J=8.8 Hz, 1H), 8.37(d, J=8.7Hz, 1H), 8.26(d, J=8.7Hz, 1H), 8.21(d, J =7.6Hz, 1H), 8.09(d, J=8.7Hz, 1H), 7.95(d, J=7.6Hz, 1H). 13 C NMR (150 MHz, DMSO) δ 130.81, 129.19, 124.72, 124.21, 40.39, 40.25, 40.11, 39.97, 39.83, 39.69, 39.56. Calculated exact mass: m / z 334.936, MALDI TOF-MS: m / z 335.889[M+H] + .

[0049] 2) Compound TPEB-p-NO 2 Synthesis

[0050] 1mmol compound 2, 1.1mmol 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylethenyl)phenyl)-1,3,2-dioxa Borolane, 0.05 mmol tetrakistriphenylphosphine palladi...

Embodiment 3

[0051] Embodiment 3: In tetrahydrofuran solvent, compound TPEB-m-NO 2 and TPEB-p-NO 2 The change of fluorescence spectrum of water probe with the increase of water addition

[0052] Get the TPEB-m-NO prepared in Example 1 2 and the TPEB-p-NO prepared in Example 2 2 Water fluorescent probe, dissolved in THF, made 1 × 10 -3 mol / L stock solution. Take 30μL from the stock solution and add it to a 5mL centrifuge tube, and configure 3mL of THF / water solution with different water contents (0%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%) to test its fluorescence properties. Probe TPEB-m-NO 2 and TPEB-p-NO 2 The changes of fluorescence spectrum and fluorescence intensity with the increase of water content are as follows: Figure 7 to Figure 10 shown. Figure 7 with Figure 9 The insets in are respectively the probe TPEB-m-NO 2 and TPEB-p-NO 2 Emission images of water / THF solutions at different water contents, taken under 365nm UV light. For the measurement of fluores...

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Abstract

The invention discloses a fluorescent probe for detecting water content in an organic solvent and its preparation method and application. There are two fluorescent probes named TPEB-m-NO respectively. 2 , TPEB‑p‑NO 2 , the corresponding chemical structural formula is shown in formula I and formula II; it is made of raw material 4,7-dibromobenzo[c][1,2,5]thiadiazole, (3-nitrophenyl)boronic acid or ( 4‑nitrophenyl)boronic acid, 4,4,5,5‑tetramethyl‑2‑(4‑(1,2,2‑triphenylvinyl)phenyl)‑1,3,2‑di The oxaborolane is synthesized and purified in two steps under the action of a catalyst; the invention also discloses spectral properties such as fluorescence changes of the fluorescent probe in the process of detecting solvent water. Research proves that the fluorescent probe of the present invention can quantitatively detect trace amounts of water in tetrahydrofuran and dioxane through the joint action of twisted intramolecular charge transfer and aggregation-induced luminescent mechanism.

Description

technical field [0001] The invention belongs to the field of organic fluorescent molecular probes, and in particular relates to a fluorescent probe for detecting water content in organic solvents, a preparation method and application thereof. Background technique [0002] Water is generally considered to be the most common impurity in organic solvents. Since the presence of water will seriously affect the product yield as well as chemical activity and application range, accurate and rapid quantification of water content in gas / liquid organic products during the experiment is very important to maintain product quality, yield and reliability. In addition, the determination of trace amounts of water is also very important for experimental safety. For example, the commonly used solvents for Grignard reaction are tetrahydrofuran and diethyl ether, and the reaction system must be absolutely anhydrous during the Grignard reagent reaction process. If a certain amount of water is co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/14C09K11/06G01N21/64
CPCC07D285/14C09K11/06C09K2211/1007C09K2211/1051G01N21/643G01N2021/6417G01N2021/6432
Inventor 张然孙浩倪中海
Owner CHINA UNIV OF MINING & TECH
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