基于氨基偶氮苯的光和pH响应聚[(三甲基丙烯酸乙酯胺)8-(4-氨基-4'-甲基丙烯酰胺基偶氮苯)1](T8A1)的合成与表征

doi:10.7503/cjcu20140155

高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (9): 2043.doi: 10.7503/cjcu20140155

基于氨基偶氮苯的光和pH响应聚[(三甲基丙烯酸乙酯胺)₈-(4-氨基-4'-甲基丙烯酰胺基偶氮苯)₁](T₈A₁)的合成与表征

蒋红波, 龚成斌, 王强(), 唐倩(), 马学兵

西南大学化学化工学院, 重庆市应用化学重点实验室, 重庆 400715

收稿日期:2014-02-27 出版日期:2014-09-10 发布日期:2019-08-01
作者简介:联系人简介: 唐倩, 女, 博士, 副教授, 主要从事有机功能材料研究. E-mail: qiantang@swu.edu.cn。王强, 男, 讲师, 主要从事应用化学研究. E-mail: wq52@swu.edu.cn。
基金资助:
国家自然科学基金(批准号: 20872121)、重庆市自然科学基金(批准号: CSTC 2013jcyjA50026)、中央高校基本科研业务费专项资金(批准号: XDJK2012C061)和西南大学博士基金(批准号: SWU2008075)资助

Synthesis and Characterization of Novel Photo- and pH-Responsive Poly[8-1]

JIANG Hongbo, GONG Chengbin, WANG Qiang(), TANG Qian(), MA Xuebing

The Key Laboratory of Applied Chemistry of Chongqing, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China

Received:2014-02-27 Online:2014-09-10 Published:2019-08-01
Supported by:
Supported by the National Natural Science Foundation of China(No.20872121), the Fundamental and Advanced Research Program of Chongqing of China(No.2013jcyjA50026), the Fundamental Research Funds for the Central Universities of China(No.XDJK2012C061) and the Southwest University Doctoral Fund, China(No.SWUB2008075)

摘要/Abstract

摘要：

以对硝基苯胺为原料, 经过偶联、还原和酰化反应, 合成了4-氨基-4'-甲基丙烯酰胺基偶氮苯(AMAB); 将三乙醇胺和甲基丙烯酰氯反应制得水溶性的十字交联剂三甲基丙烯酸乙酯胺(TMAEA); 将AMAB和TMAEA进行自由基沉淀聚合反应, 制得基于氨基偶氮苯的新型纳米级聚合物聚[(三甲基丙烯酸乙酯胺)₈-(4-氨基-4'-甲基丙烯酰胺基偶氮苯)₁](T₈A₁), 并用紫外-可见光谱(UV-Vis)、红外光谱(IR)、热失重(TG)和扫描电子显微镜(SEM)对T₈A₁进行了表征. 结果表明, T₈A₁在水中具有光和pH双重响应性能, 弥补了传统的偶氮苯类材料仅能在有机溶剂中具有响应的缺陷, 具有广阔的仿生应用前景.

关键词: 4-氨基-4'-甲基丙烯酰胺基偶氮苯, 三甲基丙烯酸乙酯胺, 光响应, pH响应

Abstract:

A photo-responsive functional monomer 4-amino-4'-methylacrylamide azobenzene(AMAB) was synthesized by coupling, reduction, and acylation reaction with 4-nitroaniline as the starting material. A water-soluble cross-linker triethylacrylateamine(TMAEA) was synthesized by acylation reaction with triethanolamine and methacrylic chloride and confirmed by nuclear magnetic resonance(NMR). A novel photo- and pH-responsive polymer: poly[(triethylacrylateamine)₈-(triethylacrylateamine)₁](T₈A₁) was successfully prepared by radical polymerization with AMAB and TMAEA using azo bisisobutyronitrile(AIBN) as the initiator. The T₈A₁ was characterized by thermeagravimetry analysis(TGA), infrared(IR), scanning electromic microscoy(SEM), and ultravidet visible(UV-Vis). The T₈A₁ exhibited both photo- and pH-response in water, which overcame the shortcoming of conventional azobenzene derivatives that they could only work in organic solvents and lose efficiency in aqueous media. These results made T₈A₁ amenable for applications in multi-stimuli responsive systems and biotechnology.

Key words: 4-Amino-4'-methylacrylamide azobenzene, Triethylacrylateamine, Photo-responsive, pH-responsive

中图分类号:

TrendMD:

蒋红波, 龚成斌, 王强, 唐倩, 马学兵. 基于氨基偶氮苯的光和pH响应聚[(三甲基丙烯酸乙酯胺)₈-(4-氨基-4'-甲基丙烯酰胺基偶氮苯)₁](T₈A₁)的合成与表征. 高等学校化学学报, 2014, 35(9): 2043.

JIANG Hongbo, GONG Chengbin, WANG Qiang, TANG Qian, MA Xuebing. Synthesis and Characterization of Novel Photo- and pH-Responsive Poly[8-1]. Chem. J. Chinese Universities, 2014, 35(9): 2043.

图/表 8

Fig.1 Synthetic routes of AMAB

Fig.2 IR spectra of AMAB(a) and T8A1(b)

Fig.3 UV-Vis spectra of AMAB in water(2.0×10-5 mol/L) upon irradiation at 410 nm(A) and 450 nm(B) Insets: the kinetics of the photoisomerization of AMAB.

Fig.4 UV-Vis spectra of T8A1 in water(8.4×10-4 g/mL) upon irradiation at 410 nm(A) and 450 nm(B) Insets: the kinetics of the photoisomerization of AMAB.

Fig.5 Reversibility of photoisomerization processes of the azobenzene chromophores in T8A1

Fig.6 UV-Vis spectra of the polymer aqueous at different pH values(A) and change in absorbance at 398 nm of T8A1 suspension(B)

Fig.7 SEM photographs of T8A1 with different magnifications

Fig.8 TGA curves of T8A1(a) and AMAB(b)

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基于氨基偶氮苯的光和pH响应聚[(三甲基丙烯酸乙酯胺)₈-(4-氨基-4'-甲基丙烯酰胺基偶氮苯)₁](T₈A₁)的合成与表征

Synthesis and Characterization of Novel Photo- and pH-Responsive Poly[8-1]

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