中国有机氟化合物卤键研究

doi:10.6023/cjoc201812026

摘要/Abstract

综述了中国学者在有机碘代和溴代氟化物的卤键研究方面的进展.从1987至1993年，陈庆云等发现全氟碘代烷作为Lewis酸可以和胺、醚和六甲基磷酰胺等Lewis碱形成供体-受体相互作用，代表了早期研究现在被称为卤键的非共价键作用力的重要进展.2001年以来，多个研究组利用卤键开展晶体工程研究.朱士正等首次证实，全氟-α，v-二碘烷烃可以和胺、醚和六甲基磷酰胺等通过卤键形成一维扩展阵列结构，晋卫军等研究了卤键驱动的全氟碘代芳烃与氮杂芳环的共晶结构，张丹维和黎占亭等利用卤键诱导产生了双螺旋及四螺旋超分子聚合物.晋卫军等研究了C—I…p卤键在晶体工程中的应用.利用卤键诱导，王栋和万立骏等在表面实现了三角型芳香分子共组装形成二维蜂窝型阵列结构，王力彦等从两个聚合物或有机分子构筑了单层膜结构和实现了层-层自组装控制.赵新和黎占亭等合成了并入三个二氟碘甲基的三臂分子，基于氢键诱导的折叠型受体，建立了溶液相多位点卤键结合的识别模式.胡文平、龚和贵、廖良生等利用卤键提高了若干共轭有机分子的不同的材料性能.多个研究组利用卤键成功控制或提高不同类型的有机反应的选择性.

关键词: 卤键, 有机氟化合物, 晶体工程, 分子识别, 自组装, 螺旋体, 人工折叠体, 电子转移反应

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

引用此文

刘传志, 王辉, 张丹维, 赵新, 黎占亭. 中国有机氟化合物卤键研究[J]. 有机化学, 2019, 39(1): 28-37.

Liu Chuan-Zhi, Wang Hui, Zhang Dan-Wei, Zhao Xin, Li Zhan-Ting. Study on Halogen Bonding of Organofluorine Compounds in China[J]. Chin. J. Org. Chem., 2019, 39(1): 28-37.

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