高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 468.

• Physical Organic Chemistry • 上一篇    下一篇

Synthesis of Calix[6]arene-Porphyrin Receptors and Study on their Catalytic Performance in Epoxidation of Styrene

Donghong Li, Shuhua Chen, Huaming Zhao   

  1. Department of Chemistry, Sichuan University, Chengdu 610064
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 基金资助:
    National Nature science Foundation of China

Synthesis of Calix[6]arene-Porphyrin Receptors and Study on their Catalytic Performance in Epoxidation of Styrene

Donghong Li, Shuhua Chen, Huaming Zhao   

  1. Department of Chemistry, Sichuan University, Chengdu 610064
  • Online:1998-12-31 Published:1998-12-31
  • Supported by:
    National Nature science Foundation of China

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被引次数

7

摘要： The artificial receptors with multiple recognition site had been synthesized by linking two unsymmetrical monofunctionalized porphyrin to p-tert-butyl calix[6]-arene via two flexible chain, followed by inserting metal ion into the porphyrin species.The structures (see Fig 1) of these calix[6]arene-diporphyrins and their metal complexes were confirmed by UV-vis spectra, IR spectra, mass spectra, 1NMR spectra(600 MHz) and/or 13C NMR. Their conformations were investigated preliminarily by UV-vis spectra and computer simulation. In constrast with the correspounding porphyrin monomer, the soret bond of calix[6]arene-diporphyrins in UV-vis spectra showed hypsochromic shift. This phenomenon suggested that two porphyrin rings maintain a face to face parallel conformation, as confirmed by computer simulation that showed the conformation energy is the lowest as two porphyrin rings hold such a conformation. Besides, simplicity of the 1NMR spectra indicates that the conformation of calix[6]arene-diporphyrin possesses high symmetry. Therefore,the calix[6]arene must be cone conformation.

Abstract: The artificial receptors with multiple recognition site had been synthesized by linking two unsymmetrical monofunctionalized porphyrin to p-tert-butyl calix[6]-arene via two flexible chain, followed by inserting metal ion into the porphyrin species.The structures (see Fig 1) of these calix[6]arene-diporphyrins and their metal complexes were confirmed by UV-vis spectra, IR spectra, mass spectra, 1NMR spectra(600 MHz) and/or 13C NMR. Their conformations were investigated preliminarily by UV-vis spectra and computer simulation. In constrast with the correspounding porphyrin monomer, the soret bond of calix[6]arene-diporphyrins in UV-vis spectra showed hypsochromic shift. This phenomenon suggested that two porphyrin rings maintain a face to face parallel conformation, as confirmed by computer simulation that showed the conformation energy is the lowest as two porphyrin rings hold such a conformation. Besides, simplicity of the 1NMR spectra indicates that the conformation of calix[6]arene-diporphyrin possesses high symmetry. Therefore,the calix[6]arene must be cone conformation.

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