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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (20): 1866-1870. 上一篇    下一篇

研究论文

2-(2,5-二羟基苯基)-5-甲基-2,5-二氢吡咯并[3,4]富勒烯的合成和电子光谱的理论研究

尹起范1,2，朱玉兰*,1,2，曹 丽1，阚玉和a,c, 周建峰1，南京熙2，苏忠民3   

  1. (1淮阴师范学院化学系 江苏省低维材料化学重点建设实验室 淮安 223300)
    (2延边大学理工学院化学系 延吉 133002)
    (3东北师范大学化学学院功能材料化学研究所 长春 130024)
  • 投稿日期:2005-12-01 修回日期:2005-06-17 发布日期:2010-12-10
  • 通讯作者: 朱玉兰

Synthesis of [2-(2,5-Dihydroxyphenyl)-5-methyl-2,5-dihydropyrrolino]- [3,4]fullerene and Theoretical Studies on Its Electronic Spectra

YIN Qi-Fan1,2, ZHU Yu-Lan*,1,2, CAO Li1, KAN Yu-He1,3, ZHOU Jian-Feng1, NAN Jing-Xi2, SU Zhong-Min3   

  1. (1 Department of Chemistry, Huaiyin Teachers’ College, Jiangsu Key Laboratory for Chemistry of
    Low-dimensional Materials, Huai′an 223300)
    (2 Department of Chemistry, Science and Engineering College, Yanbian University, Yanji 133002)
    (3 Institute of Functional Material Chemistry, Northeast Normal University, Changchun 130024)
  • Received:2005-12-01 Revised:2005-06-17 Published:2010-12-10
  • Contact: ZHU Yu-Lan

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利用丙氨酸和2,5-二羟基苯甲醛所形成的亚胺叶立德与C60发生1,3-偶极环加成反应, 合成并分离、纯化制备了一种新的C60吡咯烷衍生物: 2-(2-5-二羟基苯基)-5-甲基-2,5-二氢吡咯并[3,4]富勒烯. 通过1H NMR, FT-IR, UV-vis和元素分析确定了其结构, 研究了体系的电化学和荧光性质. 采用密度泛函的方法, 在B3LYP/6-31G水平上对分子的几何构型进行了优化, 得到稳定的几何构型; 运用INDO/S方法计算了化合物的电子光谱, 计算结果434.2 nm与实验值432.0 nm基本一致.

关键词: C60吡咯烷衍生物, 循环伏安, 电子光谱, 密度泛函

A new compound [2-(2,5-dihydroxyphenyl)-5-methyl-2,5-dihydropyrrolino][3,4]fullerene was synthesized by the 1,3-dipolar cycloaddition reaction between the fullerene (C60) and azomethine ylide (prepared from 2-aminopropanoic acid and 2,5-dihydroxybenzal), which was characterized by 1H NMR, FT-IR, UV-vis spectra and elemental analysis. Its properties of electrochemistry and fluorescence were also studied. The geometry configurations of the compound were optimized using the density functional theory at B3LYP/6-31G level. The electronic spectra of the compound were studied by INDO/S method. The computational result (434.2 nm) accorded with the experimental one (432.0 nm).

Key words: C60-pyrrolidine derivative, cyclic voltammetry, electronic spectra, density functional theory