Sulfonated acetone-formaldehyde-amine fluorescent polymer as well as preparation method and application thereof

A technology of fluorescent polymer and sulfonated acetone, applied in the field of fluorescent polymer materials, can solve the problems of expensive raw materials, complex synthesis steps and the like, and achieve the effects of good water solubility, simple preparation process and high fluorescence intensity

Active Publication Date: 2016-09-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, organic light-emitting polymers with conjugated structures in the prior art have disadvantages such as complex synthesis steps and relatively expensive raw materials during the synthesis process.

Method used

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  • Sulfonated acetone-formaldehyde-amine fluorescent polymer as well as preparation method and application thereof
  • Sulfonated acetone-formaldehyde-amine fluorescent polymer as well as preparation method and application thereof
  • Sulfonated acetone-formaldehyde-amine fluorescent polymer as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0033] Use 1.2g NaOH solid to prepare NaOH aqueous solution with pH=12, take 5.0mL ethylenediamine liquid and add dropwise to the above alkaline solution, then add dropwise 6.16mL acetone and 5.74mL aqueous formaldehyde solution with a mass fraction of 37%, and stir under reflux at 40°C React for 30min; then add 5.24g of Na 2 SO 3 Solid, heat up to 70°C in a closed environment, continue to reflux for 5 hours; rotate the obtained reaction solution at 50°C to remove residual acetone and formaldehyde, adjust the pH to 2 with HCl solution with a mass fraction of 20%, put it into a dialysis bag for dialysis Purify for 7 days, then concentrate and freeze-dry to obtain a powdery solid product, which is a sulfonated acetone-formaldehyde-amine fluorescent polymer. The synthetic route diagram of the polymer obtained in the present embodiment is as follows figure 1 shown.

Embodiment 2

[0035] Use 0.5g of KOH solid to prepare KOH aqueous solution with pH=10, take 2.0g of 1,5-pentanediamine liquid and add dropwise to the above alkaline solution, then add dropwise 8.2mL of acetone and 11.5mL of 37% formaldehyde aqueous solution, 50 The reaction was stirred at reflux for 1 h at ℃; then 6.75 g of K was added 2 SO 3 Solid, continue to react at 85°C for 4h; Rotate the obtained reaction solution at 50°C for 30min to remove residual acetone and formaldehyde, then adjust the pH to 3 with HCl solution with a mass fraction of 20%, put it into a dialysis bag for dialysis and purification for 5 days, After concentrating and freeze-drying, a yellow powdery solid product is obtained, which is a sulfonated acetone-formaldehyde-amine fluorescent polymer.

Embodiment 3

[0037] Take 5.0g of 1,8-octanediamine and add it to the pre-prepared KOH aqueous solution (0.6g KOH solid) with pH = 11, stir until it is completely dissolved, then add 16.8mL of acetone and 20.0mL of formaldehyde aqueous solution (37%, wt%), stir vigorously to make it evenly mixed, heat up to 60°C for reflux reaction for 30min; then add 8.56g of Na 2 SO 3 Solid, continue to react at 85°C for 4h; Rotate the reaction solution at 50°C for 30min to remove residual acetone and formaldehyde, then use HNO 3 The pH of the solution (20%, wt%) was adjusted to 3, and a large amount of white solid was precipitated, which was filtered, rinsed with pure water, and vacuum-dried to obtain a white powdery solid product, which was a sulfonated acetone-formaldehyde-amine fluorescent polymer.

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Abstract

The invention belongs to the technical field of fluorescent polymer materials and discloses a sulfonated acetone-formaldehyde-amine fluorescent polymer as well as a preparation method and application thereof. The preparation method comprises the following steps: preparing alkaline liquid with pH of 10-12 at normal temperature; sequentially and dropwise adding amine substance, acetone and formaldehyde aqueous solution into the alkaline liquid, and stirring for reaction for 0.5-3h at a temperature of 40-60 DEG C; adding a sulfonating agent and reacting for 2-10h at 65-80 DEG C; evaporating the reaction produced liquid at a temperature of 40-60 DEG C to remove residual acetone and formaldehyde; adding acid for acidifying the product; and purifying and drying to obtain the product. In the invention, the amine substance reacts with the formaldehyde and acetone to synthesize the new sulfonated acetone-formaldehyde-amine fluorescent polymer; and the polymer realizes a more obvious aggregation-induced emission effect, has good water solubility, high fluorescence intensity and relatively strong luminescent property in a solid state and can be applied to the fields such as fluorescence imaging, fluorescence labeling and organic electronic devices.

Description

technical field [0001] The invention belongs to the technical field of fluorescent polymer materials, and in particular relates to a sulfonated acetone-formaldehyde-amine fluorescent polymer and its preparation method and application. Background technique [0002] Organic fluorescent materials show broad application prospects in many fields such as fluorescent probes, light-emitting devices, and biochemical sensors. Due to the existence of aggregation quenching (ACQ) effect, many fluorescent materials are limited in application to a great extent. In 2001, Tang Benzhong and others discovered that a compound named Silole (silole) has anomalous fluorescence phenomenon: that is, the compound does not emit light in a dilute solution, but it shows a very strong fluorescence after adding a poor solvent to make it aggregate. Strong luminescence properties, and this phenomenon is named aggregation-induced luminescence effect (CN102153748A, CN104877666A). Because this abnormal lumin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G12/00C09K11/06
CPCC08G12/00C09K11/06C09K2211/14
Inventor 邱学青李远余伟
Owner SOUTH CHINA UNIV OF TECH
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