A New Member of the Porphyrin Family

  • Author: Jonathan Faiz
  • Published Date: 05 June 2013
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: A New Member of the Porphyrin Family

French researchers have synthesized an isostructural porphyrin analogue that does not contain pyrrol subunits. Porphyrins, which are highly conjugated 16-membered macrocycles that contain 18 delocalized π electrons, contain four pyrrol units linked by methine bridges. Denis Jacquemin, Olivier Siri, and their co-workers, Universities of Aix-Marseille and Nantes, have developed a synthetic strategy to form macrocycles that contain four nitrogen atoms separated by three carbon atoms but are "pyrrol-free".

They started by reacting 1,5-difluoro-2,4-dinitrobenzene with tetraaminobenzene tetrahydrochloride to form a macrocycle, which was then hydrogenated to form the target macrocycle. Nucleus-independent chemical shifts were used to confirm the aromaticity of the compound. An X-ray diffraction study of the protonated form showed that the macrocycle adopts a nonplanar saddle conformation because of the repulsion of the internal C–H hydrogen atoms. These macrocycles are also extremely stable, can form metal complexes, and absorb in the near-infrared region. Thus, the researchers predict that these compounds may have diverse applications.

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