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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (12): 2197-2201. 上一篇    下一篇

研究论文

[60]富勒烯与1, 1'-联茚的Diels-Alder加成物的合成与结构表征

林阳辉;张立新;蔡瑞芳;黄祖恩;吴厚铭;王中华   

  1. 复旦大学化学系.上海(200433);中国科学院上海有机化学研究所.上海(200032)
  • 发布日期:2001-12-15

Synthesis and characterization of the monoadduct C60(C9H7-C9H7) formed in Diels-Alder cycloaddition of C60 with 1, 1'-biindene

Lin Yanghui;Zhang Lixin;Cai Ruifang;Huang Zuen;Wu Houming;Wang Zhonghua   

  1. Fudan Univ, Dept Chem.Shanghai(200433);Shanghai Inst Organ Chem., CAS.Shanghai(200032)
  • Published:2001-12-15

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通过Diels-Alder环加成反应，发现可控制反应条件，使1,1'-联茚与C60反应，并高产率地得到具有新颖结构的单加成物。用HPLC，FT-IR,FD-MS及^1HNMR,^13CNMR,HMQC,HMBC等多种波谱技术对其结构进行表征，测得它的两个sp^3杂化的桥头碳的化学位移为σC:70.91，证明生成的衍生物为[6,6]闭式环加成。^13CNMR谱共给出38个信号，表明C601,1'-联茚衍生物分子具有Cs对称性；此外，还发现单加成衍生物C601,1'-联茚热稳定性好，在四氢呋喃、丙酮等极性溶剂中溶解性好，很适合于在LB膜及光限幅性能方面的研究。

关键词: 富勒烯, 茚P, 结构表征, 高速液体色谱, 红外分光光度法, 质谱法, 质子磁共振谱法, Ｌ-Ｂ膜, 化学位移

Diels-Alder cycloaddition of C60 with 1, 1'-biindene under controlled conditions affords a stable monoadduct C60(C9H7-C9H7) of novel structure, which was confirmed by HPLC, FT-IR, FD-MS, ^1H NMR, ^13C NMR, HMQC and HMBC spectra. Its two bridgehead cage carbons resonate at 70.91. The ^13C NMR spectra show 38 lines consistent with the Cs symmetry associated with [6, 6] addition. In addition, the high solubility of this adduct in polar solvents such as THF, acetone makes it suitable to a good application in the investigation of LB film and optical limiting properties.

Key words: FULLERENES, INDENE P, STRUCTURE CHARACTERISTICS, HIGH SPEED LIQUID CHROMATOGRAPHY, INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, PROTON MAGNETIC RESONANCE SPECTROMETRY, L-B MEMBRANE, CHEMICAL SHIFT

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