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2-Aryl-3H-1,3-Benzazaphosphole Oxides: Synthesis, Optical Properties, and Excited State Intramolecular Proton
Hiroaki Nakagomi1, Nina Murayama1, Rika Takegami2
1Department of Fundamental Sciences, Graduate School of Science and Technology, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.
Abstract:
Inclusion of a heteroatom to the phosphole ring is a promising strategy to intrinsically modulate the optical properties of phosphole derivatives. We report on a series of 2-aryl-3H-1,3-benzazaphosphole oxides that were efficiently prepared via sequential C-P cross-coupling, dehydrative [3+2] cycloaddition, and ring-oxidation reactions. The inclusion of one nitrogen atom into the benzophosphole framework caused red shifting of the absorption and emission maxima, reflecting the greater stabilization of the LUMO level. 2-(2-Hydroxyphenyl)benzazaphosphole oxide underwent excited state intramolecular proton transfer and emitted a weak fluorescence from the excited state of the N-H tautomer.
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