A precision structural model for fullerenols

	A precision structural model for fullerenols
	Wang ZZ(王真真); Chang XL(常雪灵); Zhao YL(赵宇亮); 高兴发;Wang, ZZ; Chang, XL; Lu, ZH; Gu, M; Zhao, YL; Gao, XF
刊名	CHEMICAL SCIENCE
	2014
卷号	5 期号:8 页码:2940-2948
英文摘要	Fullerenol is one of the main precursors of fullerene-based materials, which is promising for various biological applications because of its unusual biocompatibility and biofunctionality. However, the functional groups, acidity and reducibility, which substantialize the applications of fullerenols, remain open questions. Using density functional theory calculations, we investigated reaction mechanisms underlying the acidity and reducibility of C-60 fullerenols. On the basis of theoretical insights combined with synthesis, IR and NMR structural characterization of C-13-labeled C-60 fullerenols, we identified the functional groups and developed and verified a structural model for C-60 fullerenols. The results show a strong dependence of acidity and reducibility on the hydroxyl distributions of fullerenols. Fullerenols with stable pi-electron configurations on C-60 cores, in which no double bonds have to be placed in conjugated pentagonal rings when drawing their Kekule structures, have low acidities and reducibilities. Contrarily, fullerenols with unstable pi-electron configurations have high acidities and reducibilities. For fullerenols with different hydroxyl distributions, the calculated acid dissociation constants range from -17.55 to 15.21, and the calculated redox potentials range from -0.87 to 1.32 V. Hydroxyls with high acidities and reducibilities unlikely survive in fullerenols synthesized using alkali, oxidizing conditions. Instead, they exist as the corresponding conjugate bases or oxidized products. This structural prediction agrees with our NMR results and the previous experiments. The proposed structural model is able to interpret the main IR and NMR spectroscopic and electronically paramagnetic properties of C-60 fullerenols without the disadvantages of the previous models.
学科主题	Chemistry
收录类别	SCI
WOS记录号	WOS:000338652900003
公开日期	2016-05-03
内容类型	期刊论文
源URL	[http://ir.ihep.ac.cn/handle/311005/224887]
专题	高能物理研究所_多学科研究中心
推荐引用方式 GB/T 7714	Wang ZZ,Chang XL,Zhao YL,et al. A precision structural model for fullerenols[J]. CHEMICAL SCIENCE,2014,5(8):2940-2948.
APA	王真真.,常雪灵.,赵宇亮.,高兴发；Wang, ZZ.,Chang, XL.,...&Gao, XF.(2014).A precision structural model for fullerenols.CHEMICAL SCIENCE,5(8),2940-2948.
MLA	王真真,et al."A precision structural model for fullerenols".CHEMICAL SCIENCE 5.8(2014):2940-2948.