Synthesis of strapped, dimeric, and trimeric porphyrins based on intramolecular macrocyclization reactions

  • Osuka A
  • Kobayashi F
  • Maruyama K
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Strapped porphyrins I [e.g., X = O(CH2)nO; n = 3-6, 10; X =4-O2CC6H4CO2, 4-OCH2C6H4CH2O] were prepd. directly by the acid-catalyzed condensation reaction of 3,3'-diethyl-4,4'-dimethyl- 2,2'-dipyrrylmethane with 2-OCHC6H4XC6H4CHO-2. Dimeric and trimeric porphyrins with coplanar and orthogonal (T-shape) geometries were also synthesized in good yields as an application of this method. In the strapped porphyrins, the distortion of the porphyrin ring increases systematically on shortening the strap linkage, which is confirmed by their 1H-NMR data, red shifted absorption, and fluorescence spectra. In the coplanar dimeric and trimeric porphyrins, electronic interactions between the porphyrins distinctly obsd., while in the orthogonal T-shaped dimers and H-shaped trimers, appreciable electronic interactions were not obsd.

Author-supplied keywords

  • bis(2-formylphenyl)ether
  • cyclization
  • porphirin

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  • A Osuka

  • F Kobayashi

  • K Maruyama

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