Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (02): 325-331.DOI: 10.6023/cjoc201210010 Previous Articles     Next Articles


新型[1+1] Schiff碱大环化合物的合成与表征

胡鹏a, 郭思颖a, 张奇龙b, 张云黔a, 朱必学a   

  1. a 贵州大学大环及超分子化学重点实验室 贵阳 550025;
    b 贵阳医学院化学教研室 贵阳 550004
  • 收稿日期:2012-10-09 修回日期:2012-11-03 发布日期:2012-11-15
  • 通讯作者: 朱必学
  • 基金资助:

    国家自然科学基金(No. 21061003);贵州省国际合作(No. (2009)700104)资助项目.

Synthesis, Characterization of Novel [1+1] Schiff Base Macrocyclic Compounds

Hu Penga, Guo Siyinga, Zhang Qilongb, Zhang Yunqiana, Zhu Bixuea   

  1. a Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025;
    b Department of Chemistry, Guiyang Medical College, Guiyang 550004
  • Received:2012-10-09 Revised:2012-11-03 Published:2012-11-15
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21061003) and the International Cooperation Foundation of Guizhou Province [No. (2009)700104].

Two novel [1+1] Schiff base macrocyclic compounds 4 and 5 have been synthesized from Precursor 1 [1,7-bis(2'-formylphenyl)-4-aza-1,7-dioxa-4-(4'-toluenesulfonyl)heptane] and Precursor 2 [1,7-bis(2'-formylphenyl)-1,4,7- trioxaheptane] with diamine 3 [N,N'-(2-aminophenyl)pyridine-2,6-dicarboxamide] via condensation and cyclizaction in acid-catalyzed condition, respectively, and the structures were characterized by elemental analysis, 1H NMR, IR and MS techniques. Simultaneously, the crystal structures of two compounds 4 and 5 were determined by X-ray diffraction analysis. The X-ray single crystal analysis reveals that each of the two macrocycles 4 and 5 exhibits twisted “figure eight” conformation due to the strong intramolecular hydrogen bonding interactions, and the stabilized structure in part by the intramolecular π-π stacking interactions between the two benzene rings. The studies on the UV-vis absorption spectra show that the two macrocycles 4 and 5 have a selective recognition for La3+ ion.

Key words: Schiff base, macrocyclic compound, synthesis, crystal structure