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

doi:10.7503/cjcu20140155

Abstract

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

CLC Number:

TrendMD:

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

Figures/Tables 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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