Almost half a century ago, aromatic azides were shown to be viable candidates as photolabels, a result of the ability to generate singlet nitrene intermediate to perform insertion reactions across a variety of chemical bonds. Since then, much effort has been directed at elucidating the numerous reaction pathways that are possible for a nitrene to follow, along with probing the various physical and chemical parameters that dictate which degradation pathway the intermediate will take. To date, however, relatively little research into the field of polynitrene-aromatic compounds has been explored; these high-energy species contain properties that translate to several potential applications within fields such as polymer chemistry, photocrosslinking agents, and molecular magnetic materials. To explore the fundamental photochemical properties of polyazido-aromatic compounds, three diazido-benzene derivatives were synthesized to act as chemical precursors to their corresponding nitrenes. Photocleavage of the azido N—N<sub>2</sub> bond via laser flash photolysis yields molecular nitrogen and the aromatic biradical nitrenes, which was detected with transient absorption spectroscopy. In this talk, photophysics and product studies of these diazido compounds will be discussed.

Photochemistry of polyazido-aromatic compounds

256th National Meeting (2018)

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