Our research program is focused on investigating the utility of anti-aromatic boroles as regents for the synthesis of heteroarenes.1 Specifically, these heteroarenes are hybrid inorganic/organic analogues of benzene that have boron and an adjacent lone pair bearing heteroatom that effectively serve as a two pi-electron substitute for a C=C unit.2 Conjugated boracycles are attractive synthetic targets as these species have potential applications in electronic devices and medicinal chemistry. Through this chemistry we have been able to prepare a diverse array of monocyclic heterocycles via the insertion of readily available substrates into boroles. The UV/Vis and fluorescence spectra of the monocyclic species demonstrate significant redshifts in comparison to their carbonaceous counterparts. Our current efforts are focused on enhancing the photophysical properties of these boron containing heteroarenes by preparing systems with extended conjugation that represent analogues of polycyclic aromatic hydrocarbons (PAHs).3

The synthesis of boron-containing heteroarenes and examination of their photophysical properties

256th National Meeting (2018)

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