Pnictogen-Rich Heterocycles Derived from a Phosphadiazonium Cation

Chemistry. 2024 May 2;30(25):e202400569. doi: 10.1002/chem.202400569. Epub 2024 Mar 13.

Abstract

Heterocycles that pair main group elements and nitrogen are extremely important within the π-conjugated heterocycles research community. Compared to the vast number of boron-nitrogen heterocycles, those that include phosphorus are less common. Furthermore, the use of phosphorus-nitrogen triple bonds of any type to prepare such compounds is unprecedented. Here, we pair pyridyl hydrazonide ligands with phosphadiazonium cations and demonstrate that the chelated Mes*NP group is directly implicated in the photophysical and redox properties observed for the resulting heterocycles. In doing so, we introduce a novel building block for the production of phosphorus-containing heterocycles that could find use in small molecule activation and catalysis or as the functional component of emerging organic electronics.

Keywords: Main group chemistry; heterocycles; hydrazones; phosphadiazonium cations; π-conjugated materials.