Abstract
Abstract Triarylborane–phenanthroimidazole conjugates 1 and 2 linked by a biphenylene and phenylene group, respectively, were prepared and characterized. Both compounds are highly fluorescent ( Φ = 0.49–0.74 for 1 and Φ = 0.71–0.92 for 2 ) and show a positive solvatochromism. Upon fluoride binding to the boron center, they exhibit a ratiometric fluorescence response (Δ λ em = 84 nm for 1 and 63 nm for 2 in acetone) accompanying a vivid emission color change. Photophysical data and TD-DFT studies suggest that intramolecular charge transfer (ICT) transition from a phenanthroimidazole donor to a borane acceptor in the neutral 1 is switched to π–π* transition of phenanthroimidazole moiety after fluoride binding. Due to the greater elevation of LUMO level by fluoride complexation, the resulting fluoride adduct [ 1 F] − fluoresces at the apparently blue-shifted region.
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