π-Extended organic architectures are a fascinating class of compounds that plays a fundamental role in the materials science. The efficient overlap of atomic orbitals along an extended net of polyaromatic systems enables outstanding properties such as strong luminescence and high charge mobilities. Large π-systems, especially linearly-fused structures, however, may be prone to oxidation or dimerization, which limits the molecular motifs that can be used to obtain fundamental understanding of their physicochemical properties. In that context, six-membered phosphorus heterocycles (6M-PHs) are particularly attractive building blocks. Their introduction into the framework of π-extended systems often leads to lowering both the LUMO and HOMO and thus decreases the chance of oxidative or photo-decomposition.[1] However, the chemistry of fused molecules based on 6M-PHs is at its early stage; benchmarking structure/properties relationships is still far from being established.<br/><br/>In this communication, I will present an overview of our research on linearly-fused π-systems based on 6M-PHs. I will describe the synthesis and properties of the diphospha penta- and hexaarenes.[2] I will also discuss the impact of the phosphorus post-functionalizations into their optoelectronic properties; most of the derivatives are highly soluble in common organic solvents and feature fluorescence quantum yields up to 84%. All-in-all, I will describe the benefits of introducing 6M-PHs into large π-extended systems.

Linearly-fused π-extended systems based on six-membered phosphorus heterocycles

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