Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction†

doi:10.7503/cjcu20150831

Abstract

Abstract:

To wider applications of silica(SiO₂) nanoparticles, the Ugi multicomponent reaction was proposed to prepare the novel polymers-silica(Oct-Alg-SiO₂) nanoparticles using amidic alginate derivatives. The structure and surface elemental composition of Oct-Alg-SiO₂ were confirmed by ¹H Nuclear Magnetic Resonance(¹H NMR) spectrometer and X-ray photoelectron spectroscopy(XPS). Additionally, the morpho-logy, size and colloid stability of Oct-Alg-SiO₂ were also investigated via transmission electron microscope(TEM), zeta potential and laser particle size analyzer. The characterization of the materials revealed that Oct-Alg-SiO₂ nanoparticles were successfully fabricated via the Ugi reaction. The amidic alginate derivatives were covalently bonded onto the surface of amino-functionalized silica(SiO₂-NH₂) nanoparticles, increasing their average diameter and tuning their zeta potential, which could exhibit good dispersion stability performance in the aqueous media. The Pickering emulsions were prepared by Oct-Alg-SiO₂ using 10% liquid paraffin as the oil phase. It is worth noting that the stable Pickering emulsions with an average size of 5.7 μm could form between the oil-water interfaces. With the increase of pH value, the volume fraction of the emulsions increased and the stability of the emulsions also improved. The cytocompatibility experimental results showed that Oct-Alg-SiO₂ nanoparticles possessed excellent biocompatibility. Oct-Alg-SiO₂ nanoparticles combined excellent colloid stability performance of SiO₂ nanoparticles and good biological properties of amidic alginate derivatives, possessing great potentials in biomedical applications.

Key words: Ugi multicomponent reaction, Silica nanoparticles, Amphipathic, Pickering emulsions, Amidic alginate derivatives

CLC Number:

TrendMD:

YAN Huiqiong, CHEN Xiuqiong, LI Jiacheng, FENG Yuhong, WU Jianbo, LIN Qiang, SHI Zaifeng, WANG Xianghui. Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction^†[J]. Chem. J. Chinese Universities, 2016, 37(5): 1018.

Figures/Tables 8

Scheme 1 Schematic illustration of the preparation of Oct-Alg-SiO2

Scheme 2 Synthetic routes of Oct-Alg-SiO2

Fig.1 1H NMR spectrum of Oct-Alg-SiO2

Fig.2 XPS spectrum of Oct-Alg-SiO2

Fig.3 TEM image(A), size distribution derived from the TEM image(B), hydrodynamic diameter distribution(C) and zeta potential distribution(D) of Oct-Alg-SiO2

Table 1 Characteristics of silica nanoparticles

Sample	Average diameter^a/nm	Hydrodynamic diameter/nm	PDI^b	Zeta potential/mV
SiO₂	65.1	92.4	0.17	-20.2
SiO₂-NH₂	73.2	159.9	0.26	13.9
Oct-Alg-SiO₂	91.8	215.7	0.31	-31.6

Fig.4 Micrographs of the Pickering emulsions stabilized by Oct-Alg-SiO2(A) Before emulsification; (B, C) 48 h after emulsification; (D) 7 d after emulsification.

Fig.5 Effect of pH value on the zeta potential and volume fraction of the Pickering emulsion

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