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Fluorescent conjugated polymer with side chain amidogen being protonized, preparing method, and application of fluorescent conjugated polymer

A technology of amino protonation and conjugated polymers, which is applied in the field of fluorescent sensing materials to achieve low detection limits and good application prospects

Active Publication Date: 2017-08-11
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the technology for detection of aldehydes is mainly based on some large-scale instruments, using high performance liquid chromatography, gas chromatography, spectrophotometry, etc. It has been reported that organic fluorescent small molecules are used for the detection of formaldehyde, and conjugated polymers are used for the detection of aldehydes. Detection has not been reported

Method used

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  • Fluorescent conjugated polymer with side chain amidogen being protonized, preparing method, and application of fluorescent conjugated polymer
  • Fluorescent conjugated polymer with side chain amidogen being protonized, preparing method, and application of fluorescent conjugated polymer
  • Fluorescent conjugated polymer with side chain amidogen being protonized, preparing method, and application of fluorescent conjugated polymer

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Embodiment 1

[0029] The preparation of two monomers for the synthesis of conjugated polymers mainly includes the following main steps:

[0030] See attached figure 1 , the preparation of monomer 1 (M1): under argon protection, 2,5-dibromohydroquinone (0.80g, 3.00 mmol), 2-([tert-butoxycarbonyl]amino)ethyl 4-Methylbenzenesulfonate (2.13 g, 6.75 mmol), anhydrous potassium carbonate (4.15 g, 30.0 mmol), 15 mL N,N-dimethylformamide, heated to 70 ℃, refluxed and stirred for 24 h. Cool to room temperature, add 200 mL of deionized water, stir well, and filter to obtain a solid. After drying, the crude product is dissolved in a small amount of ethyl acetate, and washed with ethyl acetate / n-hexane (1:2) as eluent. The product was collected on a silica gel column and the solvent was removed, and the obtained product was recrystallized from ethyl acetate / n-hexane to obtain white flocculent crystals, which were dried. Yield 1.22 g (74%). 1 H NMR (400 MHz, CDCl 3 , δ): 1.46(s, 18H), 3.55(q, 4H), 4...

Embodiment 2

[0034] See attached figure 2 , which is the structure and synthetic route of the monomers required for the preparation of two fluorescent conjugated polymers; the synthesis of the conjugated polymers used for detection includes the following main steps:

[0035] See attached figure 2 , the preparation of the precursor PPE-NBoc: monomer M1 (0.277 g, 0.50 mmol), monomer M2 (0.222 g, 0.50 mmol), (PPh 3 ) 2 PdCl 2 (35 mg, 0.050 mmol), CuI (5 mg, 0.025 mmol) were added to a pre-dried and deoxygenated flask, and under argon gas flow, 8 mL of anhydrous tetrahydrofuran and 2 mL of anhydrous diisopropylamine were added. Under argon protection, reflux and stir at 60°C for 14 h. After the reaction, cool down to room temperature, filter the reaction solution with a 0.22 μm filter head, add dropwise to 200 mL of ice-cold diethyl ether to precipitate, centrifuge to obtain a solid, and finally dry it in a vacuum oven to obtain 0.212 g (51%) of an orange-red solid . 1 H NMR (400 MHz, CD...

Embodiment 3

[0038] With the conjugated polymer PPE-NH in embodiment 2 3 + Prepared solutions for the detection of aldehydes in aqueous environments.

[0039] The concentration of the polymer solution is 2×10 -5 M (according to the repeating unit), first prepare two initial solutions of the analyte with different concentrations of 0,1 M and 0.5 M, take 2ml of polymer solution for each sample, add 20 μL of each analyte solution, and finally guarantee In the two groups of experiments, the effective concentrations of each analyte in the mixed solution were 1 mM and 5 mM respectively. After mixing, shake for 5 minutes, and then place it for 25 minutes before performing fluorescence tests one by one. All samples are prepared and used immediately. Repeat three times, the fluorescence intensity change at the maximum emission point in the fluorescence spectrum is the response. According to this method to obtain the data graph, see the appendix Figure 4 . The results show that the conjugated...

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Abstract

The invention discloses a conjugated polymer with side chain amidogen being protonized, a preparing method, and application of the conjugated polymer. Two kinds of monomers are synthesized through a Songashira coupling reaction to obtain a conjugated polymer (PPE-NBoc), and then trifluoroacetic acid is utilized to remove Boc protecting groups, so that the conjugated polymer (PPE-NH3+) with the side chain amidogen being protonized is obtained. The conjugated polymer (PPE-NH3+) can be used in the achievement of selective detection of partial aldehyde materials in a water system, and particularly used in the effective detection of glutaraldehyde in conventional medical disinfectant. Large-scale instruments are not needed, and a small-size fluorescent detector can be designed to conduct qualitative or quantitative detection.

Description

technical field [0001] The invention relates to a fluorescent sensing material, in particular to a side chain amino protonated conjugated polymer, its preparation and its sensing and detection of aldehydes in water systems. Background technique [0002] Compared with traditional sensing materials, conjugated polymers can achieve a signal amplification effect due to their role as molecular wires, and their structures can be easily adjusted to achieve a specific function. By modifying specific functional groups, a specific response to a certain class of substances can be achieved. [0003] At present, there have been reports on the synthesis and application of conjugated polymers with amino groups in their side chains or protonated amino groups in their side chains (see literature: Adv. Mater . 2013, 25, 1203-1208; Chem. Commun. 2015, 51, 4036-4039; Anal. Chem. 2016, 88, 2985-2988; Angew. Chem. Int. Ed. 2007, 46, 4667-4670; Chem. Commun. 2013, 49, 6048-6050.) Some...

Claims

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Application Information

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IPC IPC(8): C08G61/02G01N21/64C09K11/06
CPCC08G61/02C08G2261/124C08G2261/143C08G2261/228C08G2261/312C08G2261/3328C08G2261/342C08G2261/352C09K11/06C09K2211/1425G01N21/643
Inventor 范丽娟缪克松
Owner SUZHOU UNIV
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