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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (17): 1587-1594. 上一篇    下一篇

研究论文

N-甲基-2-(4'-N-乙基咔唑基)-[60]富勒烯吡咯烷及其衍生物的合成, 电荷分离态特征

王婷婷，曾和平*   

  1. (华南理工大学化学科学学院功能分子研究所 广州 510641)
  • 投稿日期:2005-01-04 修回日期:2005-05-31 发布日期:2010-12-10
  • 通讯作者: 曾和平

Synthesis, Charge-separated State Characterization of N-Methyl-2-(4'-N-ethylcarbozole)-3-fulleropyrrolidine and Its Drivatives

WANG Ting-Ting,ZENG He-Ping*   

  1. (Institute of Functional Molecular, Faculty of Chemistry, South China University of Technology, Guangzhou 510641)
  • Received:2005-01-04 Revised:2005-05-31 Published:2010-12-10
  • Contact: ZENG He-Ping

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通过1,3-偶极环加成方法在微波照射下合成了N-甲基-2-(4'-N-乙基咔唑基)-富勒烯吡咯烷(C60-Cz)和N-甲基-2- (4'-N,N-二苯基氨基)-富勒烯吡咯烷(C60-TPA), 用质谱, 1H NMR, IR等对其结构进行了表征. 用激光光解时间分辨瞬态谱研究了N-甲基-2-(4'-N-乙基咔唑基)-富勒烯吡咯烷的分子内电荷转移过程, 在近红外区观测到了长寿命电荷分离态C60•--CZ•+的存在, 其寿命为0.28 μs. 运用Gaussian 98量子化学程序包, 利用密度泛函的方法对N-甲基-2-(4'-N,N-二苯基氨基)-富勒烯吡咯烷几何构型进行了优化, 并在优化基础上用ZINDO方法计算了化合物C60-TPA的电子光谱, 计算结果表明, 光谱吸收峰在440 nm, 与实验值433 nm基本一致.

关键词: 富勒烯吡咯烷, 瞬态谱, 电荷分离态

N-Methyl-2-(N-ethylcarbozole)-fulleropyrrolidine and N-methyl-2-(4'-N,N-diphenylamino)-full- eropyrrolidine were synthesized by 1,3-dipolar cycloaddition under microwave irradiation, which were characterized by MS, 1H NMR, IR and UV-Vis. Photoinduced intramolecular electron transfer process from C60 moiety to carbazole moiety has been studied by nanosecond laser flash photolysis. The charge-separated state C60•--CZ•+ was observed in the near-IR region with its life of 0.28 μs. The electronic spectrum of the C60-TPA was studied by using ZINDO method on the basis of the optimized geometrics with B3LYP/6-31G* program. The results showed that the calculated absorption was beyond 440 nm, essentially consistent with experimental value 433 nm.

Key words: fulleropyrrolidine, nanosecond transient spectra, charge-separated state