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Direct incorporation of metal ion into β-substituted porphyrinogen skelton

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Abstract

Similar to porphyrin, porphyrinogen is regarded as a stable platform with adaptable properties. Herein we demonstrate the synthesis of metal complexes by direct incorporation of transition metals having importance on the redox activity of the ligands. Metal ions were directly incorporated by using anhydrous metal salts like CoII and CrIII in porphyrinogen core. Tetra-anion is generated by the reaction of n-BuLi and then followed by metal complex formation. Its oxidation unlike the aromatization of the porphyrin skeleton gives rise to various forms of oxidized porphyrinogen. The above aspects are particularly important for establishing metal-assisted redox chemistry of porphyrinogen ligand. The β-position of the pyrrole ring in porphyrinogens was suitably substituted by halogens and other functionalities (β-substituted porphyrinogen) which were found to be effective receptors for a wide variety of guest molecules under certain conditions. The invention, which falls under the technical heading of “organic compound synthesis,” details a novel porphyrin family chemical as well as its preparation and application, involving several steps in the preparation process. Cycloheptanone and pyrroles are initially combined in an acetone environment to create meso-cycloheptyl porphyrinogen, which is subsequently followed by metal porphyrinogens and β-substituted porphyrinogen. By using FT-IR, 1H-NMR, mass, and UV–Vis spectroscopy, the characterization was completed.

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Acknowledgements

The authors acknowledge the Central University of Jharkhand for its research facilities.

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Authors and Affiliations

  1. Department of Chemistry, Central University of Jharkhand, Ranchi, 835205, Jharkhand, India

    B. Samba Sivaiah, Roshni Kumari & Soumen Dey

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  1. B. Samba Sivaiah
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Correspondence to Soumen Dey.

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Samba Sivaiah, B., Kumari, R. & Dey, S. Direct incorporation of metal ion into β-substituted porphyrinogen skelton. J IRAN CHEM SOC 21, 87–100 (2024). https://doi.org/10.1007/s13738-023-02908-5

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  • DOI: https://doi.org/10.1007/s13738-023-02908-5

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