Synthesis and properties ofB-cyano-BODIPYs
| Autor: | M. Graça H. Vicente, Maodie Wang, Frank R. Fronczek, Quynh Do, Petia Bobadova-Parvanova, Alex L. Nguyen, Zehua Zhou, Kevin M. Smith |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemical shift chemistry.chemical_element General Chemistry Crystal structure Nuclear magnetic resonance spectroscopy Cyanation 010402 general chemistry Photochemistry 01 natural sciences Fluorescence 0104 chemical sciences Bond length chemistry.chemical_compound chemistry BODIPY Boron |
| Zdroj: | Journal of Porphyrins and Phthalocyanines. 20:1409-1419 |
| ISSN: | 1099-1409 1088-4246 |
| DOI: | 10.1142/s108842461650125x |
| Popis: | A series of boron-functionalized BODIPY dyes with cyano groups were prepared from their corresponding BF2derivatives 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 [Formula: see text]B NMR chemical shifts. The 4,4[Formula: 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/cm[Formula: see text], and rapidly accumulated within cells, localizing mainly in the lysosomes, ER and Golgi. |
| Databáze: | OpenAIRE |
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