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A series of boron-functionalized BODIPY dyes with cyano groups were prepared from their corresponding BF 2 derivatives using SnCl 4 /TMSCN at room temperature for 10 min. Replacement of the fluorines by cyano groups reduces the B–N bond lengths, decreases the charge on boron, and causes characteristic Formula: see textB NMR chemical shifts. The 4,4Formula: see text-dicyano-BODIPYs show significantly enhanced stability to acidic conditions (excess TFA) and, with one exception, enhanced fluorescence quantum yields. Furthermore, the B(CN) 2 -BODIPYs were non-cytotoxic to HEp2 cells, both in the dark and upon exposure to light (1.5 J/cmFormula: see text, and rapidly accumulated within cells, localizing mainly in the lysosomes, ER and Golgi.
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