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Fluorescent conjugated polymer containing pyrrolopyrrolidone building block, preparation method and application

A technology of rolopyrrolidone and conjugated polymers, which is applied to fluorescent conjugated polymers, the preparation method and its application can solve the problems such as the inability to realize the detection and response of various anions, and improve the response sensitivity, amplify the response effect, and operate convenient effect

Active Publication Date: 2021-09-28
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these previous reports, the polymer only has a specific response to a single anion, and cannot realize the detection response to multiple anions.

Method used

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  • Fluorescent conjugated polymer containing pyrrolopyrrolidone building block, preparation method and application
  • Fluorescent conjugated polymer containing pyrrolopyrrolidone building block, preparation method and application
  • Fluorescent conjugated polymer containing pyrrolopyrrolidone building block, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0037] See attachedfigure 1 , which is a synthetic route map of monomers required for the preparation of fluorescent conjugated polymers in the present invention. The synthesis steps of monomers used to synthesize conjugated polymers are as follows:

[0038] (1) Preparation of component 1: Dissolve potassium tert-butoxide (4.487 g, 40 mmol) in 35 mL tert-amyl alcohol in a 250 mL double-necked flask under argon protection, heat to 110°C and keep it warm 5 min. After cooling to room temperature, 4-bromobenzonitrile (6.374 g, 35 mmol) was added to the flask. Diisopropyl succinate (3.242 g, 16 mmol) was dissolved in 16 mL of tert-amyl alcohol in a constant pressure dropping funnel, and slowly added dropwise to the flask. After the dropwise addition, the temperature was raised to 110°C, and stirred under reflux for 14 h. After the reaction, the mixture was cooled to room temperature and poured into a beaker containing a mixed solution of 150 mL of ethanol and 8 mL of acetic acid...

Embodiment 2

[0043] This embodiment provides another fluorescent conjugated polymer with pyrrolopyrrolidone (DPP) as the conjugated main chain.

[0044] See attached figure 1 , which is a synthetic route map of monomers required for the preparation of fluorescent conjugated polymers in the present invention. The preparation method of the monomer M2 in the figure is: under the protection of argon, add the component 1 (1.620 g, 3.63 mmol) and potassium carbonate (1.503 g , 10.80mmol), N,N-dimethylformamide 30 mL, heated up to 120°C, stirred for 1 h, added 18-crown-6 (5.042g, 0.02mmol), and 1-bromooctane (1.401 g, 7.26 mmol) was dissolved in 5 mL N,N-dimethylformamide and slowly added dropwise to the flask. The mixture was stirred at 120°C for 6 h. After the reaction was finished, cool to room temperature, add 50 mL of deionized water to the mixture, then add 20 mL of chloroform for extraction, collect the organic phase, and wash with 50 mL of deionized water for more than 4 times, and fin...

Embodiment 3

[0048] The conjugated polymer PPE-DPP1 prepared in Example 1 was prepared into a tetrahydrofuran solution to realize responsive detection of anions.

[0049] In the detection response system, the concentration of the tetrahydrofuran solution of the conjugated polymer PPE-DPP1 is 5×10 -5 M (calculated by repeating unit), the concentration of the anion to be tested is 1×10 -3 M.

[0050] Specific operation steps: Take 2.7 mL of PPE-DPP1 tetrahydrofuran solution for each sample, add 0.3 mL of each solution of the substance to be tested, mix, and set the time intervals of 30 min, 1 h, 2 h, 4 h, and 6 h, respectively. , 8 h, 10 h, and 24 h for fluorescence testing, digitally photographed and recorded samples of the polymer solution during these time periods, and the results can be found in the attached Figure 5 , the 9 test tubes in the figure add blank and OH respectively from left to right - , F - , Cl - 、Br - , I - 、AcO - , NO 3 - and HSO 4 - . All the samples ar...

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Abstract

The invention discloses a fluorescent conjugated polymer containing a pyrrolopyrrolidone building unit, a preparation method and an application. Fluorescent conjugated polymers with pyrrolopyrrolidone structure as the main chain and different structures in the side chains were synthesized by Sonogashira coupling method. In the present invention, since pyrrolopyrrolidone is an electron-deficient system, intermolecular charge transfer can be formed with strong electron-donating anions, and the electron-donating abilities of different anions are different, which further affects the fluorescence of the conjugated polymer, thereby Responsive detection of anions is achieved. It is applied to the sensing and detection of common anions in tetrahydrofuran solution system, and has the effect of responsive detection. After testing, its pair of OH ‑ , F ‑ , Cl ‑ 、Br ‑ , I ‑ 、AcO ‑ It has a good response effect, and the color change of the polymer solution and the change of the fluorescent color can be observed with the naked eye, and the response detection to the anion can be realized conveniently.

Description

technical field [0001] The invention relates to a fluorescent conjugated polymer, a preparation method and an application thereof, and belongs to the technical field of fluorescent materials. Background technique [0002] Pyrrolopyrrolidone (DPP) small molecule is an excellent red dye, which is widely used in the field of optoelectronics and sensing due to its good luminescent properties (see literature: Chem. Soc. Rev . 2015, 44 , 58-77; J. Mater. Chem. A 2017, 5 , 11623-11633; Bioconjugate Chem. 2018, 29 , 2619-2627). In recent years, methods for introducing pyrrolopyrrolidone (DPP) structures into the main chain of conjugated polymers mainly include Suzuki coupling, Still coupling, etc. (see literature: Adv. Mater. 2017, 29 , 1606162; Sens. Actuators, B 2017, 251 , 49-56). There are also reports in the literature that the pyrrolopyrrolidone (DPP) structure is introduced into the main chain structure of the conjugated polymer using the Sonogashira coupling meth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06
CPCC08G61/124C08G2261/124C08G2261/18C08G2261/312C08G2261/3241C09K11/06C09K2211/1425C09K2211/1466
Inventor 范丽娟吴应忠
Owner SUZHOU UNIV
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