Phosphaalkenes (R2C=PR') and diphosphenes (RP=PR) represent main group analogs of alkenes (R2C=CR'2). Molecules featuring these low-coordinate phosphorus containing subunits often show structural and chemical behavior that mimic their purely organic counterparts, justifying the claim that these low coordinate phosphorus compounds are "a carbon copy". We have been working to extend this analogy to polymers and materials having extended conjugation that directly involve P=C and P=P units. Many materials, however, do not show significant photoluminescence (PL). In this presentation we will summarize past work and report on materials having significant PL and that can be said to be mimic or "photocopy" the PL properties of the phosphorus-free systems. Specifically, new materials from our labs based on 1,3-benzoxaphospholes (BOPs), 1,3-benzazaphospholes (BAPs), and higher analogues having high fluorescence quantum yields will be discussed. Computational studies have also revealed additional insights into why these materials display unique photoluminescence compared to other low-coordinate organophosphorus compounds.

Carbon-copies vs photo-copies: Shining light on luminescent low-coordinate organophosphorus compounds

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