Transformation of Phosphorus Atom in Hexacyclic Polyaromates and its Impact on Physico-Chemical Properties

A new article by authors from the Research Group of Advanced Materials and Organic Synthesis (GAMOS) has been published in The Journal of Organic Chemistry. The study focuses on the preparation and investigation of phenanthrene-based polyaromatic compounds containing a phosphorus atom. These compounds are of interest for the development of advanced functional materials, such as optoelectronics, fluorescent systems, and redox-active chromophores. Derivatization of the phosphorus center makes it possible to modify the electronic structure of the molecule and, consequently, to influence its optical and electrochemical properties.

The authors prepared a series of eight phenanthrene-derived compounds and examined how their properties change as the chemical environment of the phosphorus atom is modified. The results showed that some modifications have only a minor effect on the molecules’ properties. This applies particularly to phosphinic acid derivatives, for which the absorption, emission, and redox properties remained very similar. In contrast, replacing oxygen with sulfur or selenium in the phosphine oxide derivative led to more pronounced changes in the optical properties. This demonstrates that the photophysical properties of the resulting compounds can be finely tuned by selecting an appropriate substituent on the phosphorus atom.

The published study thus provides a comprehensive overview of how targeted transformation of the phosphorus center in an aromatic system can influence the optical and electrochemical properties of the entire molecule. The insights gained may serve as a guide for designing new organophosphorus materials with properties tailored to specific applications.

• Mizerová E., Almarza González J., Církva V., Žádný J., Storch J., Jakubec M., Beránek T.: Transformation of the Phosphorus Atom in Hexacyclic Polyaromates and Its Impact on Physicochemical Properties. J. Org. Chem. 2026, 91(20), 6884–6894. doi.org/10.1021/acs.joc.6c00184.