Synthesis and properties of B -cyano-BODIPYs
© 2016 World Scientific Publishing Company. A series of boron-functionalized BODIPY dyes with cyano groups were prepared from their corresponding BF2 derivatives using SnCl4/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 11B NMR chemical shifts. The 4,4′-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/cm2), and rapidly accumulated within cells, localizing mainly in the lysosomes, ER and Golgi.
Publication Source (Journal or Book title)
Journal of Porphyrins and Phthalocyanines
Nguyen, A., Wang, M., Bobadova-Parvanova, P., Do, Q., Zhou, Z., Fronczek, F., Smith, K., & Vicente, M. (2016). Synthesis and properties of B -cyano-BODIPYs. Journal of Porphyrins and Phthalocyanines, 20 (12), 1409-1419. https://doi.org/10.1142/S108842461650125X