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Trianionic 1,3,2‐Dioxaborine‐Containing Polymethines: Bright Near‐Infrared Fluorophores

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Trianionic polymethines of the A′–π–A–π–A–π–A′ type comprising the dioxaborine rings (A) and different electron accepting end-groups (A′) were synthesized. The obtained dyes absorb and emit light in the near-infrared region with remarkably high molar attenuation coefficients (ɛ, up to 495 000 M−1cm−1 in DMF) and fluorescence quantum yields (Φf, up to 0.73 in DMF). Thus, the novel trianionic dyes take a stand among the brightest individual fluorophores known to date—with the magnitude of fluorescence brightness (ɛ∙Φf) of 313 000 M−1cm−1 in DMF. The synthesized dyes demonstrate a minor negative solvatochromism and small Stokes shifts. The X-ray data reveal the nearly planar geometry of the trianionic chromophore. All the obtained compounds are stable in the solid state and in a solution, although the relative stability is much higher in polar aprotic than in protic solvents.

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