Switching of Aromatic Free Base Triphyrin(2.1.1) to Antiaromatic Phosphorus(V) Complexes of Triphyrin(2.1.1)
Kamakshya Nath Panda, Rima Sengupta, Ankit Kumar, Mangalampalli Ravikanth
Abstract
The aromatic 14π meso-tetraaryl triphyrin(2.1.1)s were switched to stable antiaromatic 16π P(V) complexes of triphyrin(2.1.1) by refluxing free base triphyrin(2.1.1)s with PCl3 in a mixture of solvents toluene/triethylamine for 4 h. The P(V) triphyrin(2.1.1)s were characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy and their properties were studied in detail by absorption, electrochemical, and density functional theory (DFT) studies. The studies suggested that PCl3 reduces 14π triphyrins to 16π triphyrins, which were then complexed to form stable antiaromatic P(V) complexes.
Topics & Concepts
AntiaromaticityChemistryTriethylamineTolueneBase (topology)Density functional theoryNuclear magnetic resonance spectroscopyComputational chemistryAromaticityOrganic chemistryMoleculeMathematical analysisMathematicsPorphyrin and Phthalocyanine ChemistryPhotosynthetic Processes and MechanismsMagnetism in coordination complexes