The incorporation of heavy main group elements within π-conjugated frameworks is of interest for the design of functional organic materials, especially with optoelectronic properties. Recently, the synthesis of novel substituted tellurophenes using the Zr-mediated Fagan-Nugent transmetalation method has been reported by Rivard and coworkers. They found that tellurophenes substituted with pinacolborane (Bpin) groups displayed tunable phosphorescence in the solid and aggregated states. This rare luminescence behavior is enabled by the heavy main group atom, which promotes crossover to the phosphorescent triplet state, and the bulky Bpin groups, whose restricted motion in the solid state results in the aggregation- and crystallization-induced emission. We now report the incorporation of antimony into similar stibole heterocycles. The tunability of stiboles is increased compared to the analogous tellurophenes due to the third substituent at the antimony center. We also show that the Sb(III) centers within these stiboles may undergo oxidation to afford Lewis acidic Sb(V) species.  We are currently investigating how the nature of the heterocycle substituents may be used to impart favorable photophysical properties to these new derivatives.

Novel antimony-containing heterocycles synthesized via a Zr-transfer strategy

253rd National Meeting (2017)

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