Synthesis and Antioxidant Capacity of Dendrimer Bridged Antioxidant with Semi-hindered Phenolic Groups†

doi:10.7503/cjcu20180749

Abstract

Abstract:

A dendrimer bridged antioxidant with semi-hindered phenolic groups and symmetrical structure was synthesized using 1.0G dendrimer as raw material. The structure and the purity of the dendrimer bridged antioxidant with semi-hindered phenolic groups were verified by elemental analysis, Fourier transform infrared spectoscopy(FTIR), ¹H nuclear magnetic resonance spectroscopy(¹H NMR), mass spectrometry(MS) and cryoscopic method. The antioxidant capacity of the dendrimer bridged antioxidant with semi-hindered phenolic groups was evaluated by the 1,1-diphenyl-2-picrylhydrazine(DPPH) assay and differential scanning calorimetry(DSC) method, and its antioxidant capacities was compared with those of the corresponding dendrimer bridged antioxidant with total-hindered phenol groups. The results showed that the free radical scavenging activities of the dendrimer bridged antioxidant with semi-hindered phenolic groups were affected not only by the antioxidant concentration but also by the reaction time. The antioxidant activity at the scavenging time of 30 min was about twice of which at the scavenging time of 400 min for the dendrimer bridged antioxidant with semi-hindered phenolic groups. Because of the semi-hindered phenolic effect, the antioxidant capacity of the dendrimer bridged antioxidant with semi-hindered phenolic groups was superior to that of the corresponding dendrimer bridged antioxidant with total-hindered phenolic groups in DPPH system and high density polyethylene(HDPE) resin.

Key words: Dendrimer, Semi-hindered phenol antioxidant, Antioxidant capacity

CLC Number:

TrendMD:

LI Cuiqin, ZHAI Xue, SUN Peng, GAO Yuxin, ZHANG Zhiqiu, WANG Jun, LI Feng. Synthesis and Antioxidant Capacity of Dendrimer Bridged Antioxidant with Semi-hindered Phenolic Groups^†[J]. Chem. J. Chinese Universities, 2019, 40(7): 1535.

Figures/Tables 8

Scheme 1 Synthesis of dendrimer bridged antioxidant with semi-hindered phenolic groups

Fig.1 IR spectrum of dendrimer bridged antioxidant with semi-hindered phenolic groups

Fig.2 1H NMR spectrum of dendrimer bridged antioxidant with semi-hindered phenolic groups

Fig.3 MS spectrum of dendrimer bridged antioxidant with semi-hindered phenolic groups

Fig.4 Effects of the concentration of dendrimer antioxidant with semi-hindered phenolic groups(A) and dendrimer antioxidant with total-hindered phenolic groups(B) on the activity scavenging DPPH∙Scavenging time/min: a. 400; b. 30.

Fig.5 Effects of scavenging time on the activity scavenging DPPH∙ for dendrimer bridged antioxidant with semi-hindered phenolic groups(A) and dendrimer bridged antioxidant with taotal-hindered phenolic groups(B)EC50 values at the scavenging time of 30 min(a) and 400 min(b).

Fig.6 Possible mechanisms of dendrimer bridged antioxidants with hindered phenolic groups scavenging DPPH∙

Fig.7 Oxidation induced temperature(A) and oxidation induced time(B) of series of HDPE samples with dendrimer bridged antioxidants with hindered phenolic groupsa. HDPE sample without antioxidant; b. HDPE sample with dendrimer bridged antioxidant with semi-hindered phenol groups;c. HDPE sample with dendrimer bridged antioxidant with total-hindered phenol groups.

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