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null (Ed.)Studies have previously shown that anthracene and naphthalene derivatives serve as compounds for trapping and chemically generating singlet molecular oxygen [O 2 ( 1 Δ g )], respectively. Simple and efficient synthetic routes to anthracene and naphthalene derivatives are needed, for improved capture and release of O 2 ( 1 Δ g ) in cellular environments. Because of this need, we have synthesized a dihydroxypropyl amide naphthlene endoperoxide as a O 2 ( 1 Δ g ) donor, as well as five anthracene derivatives as O 2 ( 1 Δ g ) acceptor. The anthracene derivatives bear dihydroxypropyl amide, ester, and sulfonate ion end groups connected to 9,10-positions by way of unsaturated (vinyl) and saturated (ethyl) bridging groups. Heck reactions were found to yield these six compounds in easy-to-carry out 3-step reactions in yields of 50–76%. Preliminary results point to the potential of the anthracene compounds to serve as O 2 ( 1 Δ g ) acceptors and would be amenable for future use in biological systems to expand the understanding of O 2 ( 1 Δ g ) in biochemistry.more » « less
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