Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 28-37.DOI: 10.6023/cjoc201812026 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Reviews

中国有机氟化合物卤键研究

刘传志a, 王辉a, 张丹维a, 赵新b, 黎占亭a   

  1. a 复旦大学化学系 上海 200438;
    b 中国科学院上海有机化学研究所 上海 200032
  • 收稿日期:2018-12-14 修回日期:2018-12-19 出版日期:2019-01-25 发布日期:2018-12-21
  • 通讯作者: 张丹维, 黎占亭 E-mail:zhangdw@fudan.edu.cn;ztli@fudan.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21772026,21432004)资助项目.

Study on Halogen Bonding of Organofluorine Compounds in China

Liu Chuan-Zhia, Wang Huia, Zhang Dan-Weia, Zhao Xinb, Li Zhan-Tinga   

  1. a Department of Chemistry, Fudan University, Shanghai 200438;
    b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-12-14 Revised:2018-12-19 Online:2019-01-25 Published:2018-12-21
  • Contact: 10.6023/cjoc201812026 E-mail:zhangdw@fudan.edu.cn;ztli@fudan.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21772026, 21432004).

This review summarizes studies on halogen bonding of fluorine-containing alkyl and aryl iodides in China. From 1987 to 1993, Chen et al. found that there existed donor-acceptor interaction between fluorinated organic (di)iodides, as Lewis acids, and organic Lewis bases such as amines and ethers, which represented early important advances for the research on the non-covalent force currently called as halogen bonding. From 2001 to now, several groups have used halogen bonding as driving force to conduct researches on crystal engineering. In this catogery, Zhu et al. investigated the one-dimensional self-assembly between perfluoro-α,?-diioodalkanes and amines, ethers, and hexamethylphosphamide. Jin et al. studied the complexation between fluorinated aryl iodides and various N-heterocycles, whereas Zhang and Li et al. constructed supramolecular double and quadruple helices from one or two molecular components. Jin et al. conducted extensive studies on C—I…p halogen bonding and its applications in crystal engineering. Wang and Wan et al. utilized halogen bonding to induce trianglular aromatic molecules to co-assemble into two-dimensional honeycomb arrays on surface, whereas Wang et al. utilized halogen bond to induce mono-layer and layer-by-layer self-assembly of two polymers or organic molecules. Zhao and Li et al. developed the applications of halogen bonding in solution-phase multi-site molecular recognition of foldamer receptors for ICF2-incorporated tri-armed guests. Hu, Gong, Liao et al. utilized halogen bonding to improve the material properties of a variety of organic aromatic molecules. Several groups have also used halogen bonding to increase the selectivity of a number of organic reactions. Representative examples are described, which highlight the utility of halogen bonding.

Key words: halogen bond, organofluorine compounds, crystal engineering, molecular recognition, self-assembly, helix, foldamer, electron-transfer reaction