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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Porphyrin Chemistry

Background:

  • Triphyrins are macrocyclic compounds with unique structural and electronic properties.
  • The 'confusion approach' offers a strategy to access novel porphyrinoid architectures.

Purpose of the Study:

  • To synthesize N-confused [14]triphyrin(2.1.1) and explore its chemical transformations.
  • To investigate the structure-property relationships of diverse triphyrin derivatives.

Main Methods:

  • Facile synthesis of N-confused [14]triphyrin(2.1.1).
  • Chemical conversions including oxidation, ring-opening, and metal-templated ring-closure with tetrachlorination.
  • Spectroscopic and electrochemical characterization of synthesized compounds.

Main Results:

  • Successful synthesis of N-confused [14]triphyrin(2.1.1) (1), N-confused triphyrinone(2.1.1) (2), and α-methoxy-substituted 1-OMe.
  • Acid-promoted ring-opening of 1-OMe yielded vacatatriphyrin(2.1.1) (3).
  • Copper(II) chloride treatment of 3 led to ring-closure and tetrachlorination, forming 2H-triphyrin(2.1.0) (4).

Conclusions:

  • The 'confusion approach' enables the facile synthesis of diverse triphyrin structures.
  • The resulting structural variations allow for effective tuning of aromaticity, absorption, and electrochemical properties.