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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 02: 325 - 331

DOI: https://doi.org/10.6023/cjoc201210010

Articles

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

  • Hu Peng ,
  • Guo Siying ,
  • Zhang Qilong ,
  • Zhang Yunqian ,
  • Zhu Bixue
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  • a Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025;
    b Department of Chemistry, Guiyang Medical College, Guiyang 550004

Received date: 2012-10-09

  Revised date: 2012-11-03

  Online 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].

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Abstract

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

Cite this article

Hu Peng , Guo Siying , Zhang Qilong , Zhang Yunqian , Zhu Bixue . Synthesis, Characterization of Novel [1+1] Schiff Base Macrocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 325 -331 . DOI: 10.6023/cjoc201210010

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