Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (06): 741-744. Previous Articles    

Reports

6-氨基己酸及2-氨基乙磺酸C60加成物的合成及溶解性

刘绪峰a,b,官文超*,1,程珍贤2   

  1. (1华中科技大学化学系 武汉 430074)
    (2湖北大学化学与材料科学学院 武汉 430062)
  • 收稿日期:2004-12-09 修回日期:2005-04-26 发布日期:2005-05-30
  • 通讯作者: 官文超

Synthesis and Solubility of 6-Aminohexanoic Acid and 2-Aminoethanesulfonic Acid C60 Adducts

LIU Xu-Feng1,2, GUAN Wen-Chao*1, CHENG Zhen-Xian2   

  1. (1 Department of Chemistry, Huazhong University of Science and Technology, Wuhan 430074)
    (2 Faculty of Chemistry and Material Science, Hubei University, Wuhan 430062)
  • Received:2004-12-09 Revised:2005-04-26 Published:2005-05-30
  • Contact: GUAN Wen-Chao

Preparation of water soluble fullerenes (C60) derivatives is meaningful to biological study of fullerenes. Amination reaction of amino-acid with C60 led to water soluble amino-acid C60 derivatives. Reaction of C60 with excess of NH2(CH2)5COONa+ (1) or (4) (molar ratio is 1∶10) at 80 ℃ for 24 h afforded main amino-acid C60 adducts with addition degree of 5 and 4, respectively. The yields based on the C60 added were 30% and 28%, respectively. The addition degree was influenced by the length of hydrocarbon chain of amino-acid and precipitation of C60 adducts from the reactant. C60[NH(CH2)5- COOH]5H5 (3a) and C60(NHCH2CH2SO3H)4H4 (6a) were further purified by silica column chromatography and characterized by 1H NMR, 13C NMR, IR, FAB-MS spectra and elemental analysis. The solubility of 6a was less pH dependent. The solubility of 3a in water at different pH was measured by the spectro-photometric method, exhibiting solubility of 71.81 mg•mL-1 (pH=10.25), 23.68 mg•mL-1 (pH=7) and 10.12 mg•mL-1 (pH=3.36). The ε value of 3a at 272.8 nm was 3.43×104 L•mol-1•cm-1.

Key words: 6-aminohexanoic acid, 2-aminoethanesulfonic acid, amination, fullerene