Preparation method of pH-concentration dependent tertiary amine chromophore polymer

A polymer-dependent technology, applied in the field of responsive fluorescence, can solve the problem of acid-base reversibility and concentration dependence of tertiary amine polymers, no acid-base reversibility and concentration dependence, weak fluorescence intensity of polymers, etc. problems, to achieve the effect of stable autofluorescence performance, simple and stable reaction system, and good water solubility

Active Publication Date: 2020-02-28
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fluorescence intensity of the fluorescent polymer prepared by this method is only affected by a single condition of acid or alkali, and does not have acid-base reversibility and concentration dependence, and the fluorescence intensity of the polymer is relatively weak.
Another method for preparing tertiary amine chromophore polymers is mainly based on Michael addition polymerization between mercapto groups and carbon-carbon double bond monomers. The resulting tertiary amine polymer itself is insoluble in water, and its tertiary amine polymerization has not been reported. Whether the product has acid-base reversibility and concentration dependence, and there are disadvantages that the monomers required for polymerization need to be synthesized in multiple steps, and the polymerization system is easy to cross-link

Method used

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  • Preparation method of pH-concentration dependent tertiary amine chromophore polymer
  • Preparation method of pH-concentration dependent tertiary amine chromophore polymer
  • Preparation method of pH-concentration dependent tertiary amine chromophore polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] N-methyldiethanolamine (0.119g, 1mmol), ethylene glycol diacrylate (0.170g, 1mmol) and N,N-dimethylformamide (1.19g, 10mmol) were added to the polymerization bottle, followed by Add the catalyst t-BuP to the polymerization bottle under the protection of argon 2 (50 μL, 0.1 mmol), and reacted at 25° C. for 96 h. After the reaction finishes, add acetic acid to stop the reaction, add methylene chloride to dilute, settle in n-hexane, dialyze through 3500g / mol molecular weight dialysis bag, freeze-dry to obtain the linear polymer (L-1 ), adopt the gel permeation chromatography of DMF phase to characterize the weight-average molecular weight M of polymkeric substance w.GPC =11300g / mol, molecular weight distribution PDI=1.2, the excitation wavelength of the obtained linear tertiary amine polymer in the aqueous solution is 397nm and the emission wavelength is 414nm through the fluorescence spectrum test, and the fluorescence intensity of the polymer presents a gradual increase...

Embodiment 2

[0039] Triethanolamine (0.149g, 1mmol), ethylene glycol diacrylate (0.170g, 1mmol) and N,N-dimethylformamide (1.19g, 10mmol) were added to the polymerization bottle, followed by Slowly add the catalyst t-BuP into the polymerization bottle2 (50 μL, 0.1 mmol), and reacted at 25° C. for 72 h. After the reaction finishes, add acetic acid to stop the reaction, add dichloromethane and dilute in normal hexane to settle down, obtain the hydroxyl-terminated branched polymer (B -1). The weight-average molecular weight M of the polymer was characterized by gel permeation chromatography using DMF phase w.GPC =19088g / mol, molecular weight distribution PDI=1.68, infrared spectrum and nuclear magnetic spectrum were used to confirm that the polymer with the target structure had been prepared. The excitation wavelength of the obtained hydroxyl-terminated branched tertiary amine polymer in aqueous solution is 397nm, and the emission wavelength is 414nm by fluorescence spectroscopy. The fluore...

Embodiment 3

[0041] Triethanolamine (0.149g, 1mmol), ethylene glycol diacrylate (0.340g, 2mmol) and N,N-dimethylformamide (2.4mL) were added to the polymerization bottle, followed by The catalyst (2.38g, 20mmol) was slowly added into the polymerization bottle, and reacted at 0°C for 72h. After the reaction finishes, add acetic acid to terminate the reaction, add methylene chloride to dilute, settle in normal hexane, dialyze through 3500g / mol molecular weight dialysis bag, freeze-dry to obtain the branched polymer ( B-2). The weight-average molecular weight M of the polymer was characterized by gel permeation chromatography using DMF phase w.GPC =20100g / mol, molecular weight distribution PDI=1.72, infrared spectrum and nuclear magnetic spectrum were used to confirm that the polymer with the target structure had been prepared. The obtained double bond-terminated branched tertiary amine polymer has an excitation wavelength of 397nm and an emission wavelength of 414nm in a 2 mg / mL aqueous so...

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Abstract

The invention belongs to the technical field of responsive fluorescence, and specifically discloses a preparation method of a pH-concentration dependent tertiary amine chromophore polymer. According to the preparation method, tertiary amine containing hydroxyl monomers and unsaturated acrylate double-bond monomers carry out Oxa-Michael addition solution polymerization to simply prepare a polymer,whose molecular skeleton comprises a tertiary amine structure, in one step. The preparation method does not need a step of preparing monomers, the reaction conditions are mild, the post treatment is simple, and the preparation method can be applied to large scale production. Furthermore, the prepared polymer containing a tertiary amine structure has good water solubility and bio-compatibility, ispH-concentration dependent, and has a great research value and application prospect in fields of bio-detection and drug carriers.

Description

technical field [0001] The invention belongs to the technical field of responsive fluorescence, and in particular relates to a preparation method of a pH- and concentration-dependent tertiary amine chromophore polymer. Background technique [0002] Stimuli-responsive fluorescent polymers are a class of polymer fluorescent materials that can respond to external stimuli such as temperature, pH, ionic strength (electrolyte), electric field, light, etc. The characteristic that the color will change makes it have potential application value in the fields of data storage, chemical detection, fluorescent anti-counterfeiting materials and drug carriers. pH-responsive fluorescent polymer materials are a class of materials containing basic residues or ionizable acidic residues that can accept or release protons under the trigger of environmental pH, thereby causing the transition of the fluorescent state of the polymer. [0003] In recent years, a class of polymers containing non-tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/00C09K11/06
CPCC08G73/00C09K11/06C09K2211/14
Inventor 蒋其民黄文艳薛小强杨宏军江力蒋必彪
Owner CHANGZHOU UNIV
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