Designing and synthesizing small molecules for the purpose of function enables advancements in fields ranging from pharmaceuticals to pesticides. Unfortunately, modern synthetic method development has not matched the demand for certain classes of small molecules, one example being limited protocols for accessing functionalized naphthalenes. Utilizing a thermal, dehydrogenative dehydro-Diels�Alder (DDDA) reaction, we have selectively prepared novel, naphthalene-containing compounds from styrenyl precursors, a rare transformation prior to this work. The purely thermal conditions are compatible with a variety of functionality and are thus amenable to the preparation of novel naphthalene structures. Moreover, by combining high-level theory with experiment, elucidating a general reaction mechanism(s) is possible. The synthetic advantage afforded by the DDDA reaction is demonstrated by its application to synthetic fluorophores possessing tunable chemical and photophysical properties. Scope and limitation studies of the DDDA reaction, mechanistic analysis, and application to rationally designed fluorophores will be reported on.

Dehydrogenative dehydro-Diels–Alder reaction applied to tunable synthetic fluorophores

245th National Meeting (2013)

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