Title

Synthesis and properties of B -cyano-BODIPYs

Document Type

Article

Publication Date

12-1-2016

Abstract

© 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

First Page

1409

Last Page

1419

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