Our group recently demonstrated that a diamidocarbene with a singlet ground state can undergo intersystem crossing from a singlet excited to a triplet excited state when irradiated at 380 nm. The photochemically accessible triplet state was shown to undergo Büchner ring expansion reactions with various arenes; and, remarkably, these ring-expanded products were found to be thermally reversible. While previous work described the photochemical reactions of the diamidocarbene with mono-substituted arenes, this presentation will detail new investigations into the photochemical reactivity of the diamidocarbene with polyaromatic compounds including azobenzene, naphthalene, and acridine. Additionally, the synthesis of novel carbene architectures which may be photochemically active will be discussed, including <i>in silico</i> results which we have used to identify possible candidates.

Exploring the photochemistry of diamido and related electrophilic carbenes

256th National Meeting (2018)

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