volume 20 issue 12 pages 1409-1419

Synthesis and properties ofB-cyano-BODIPYs

Alex L. Nguyen 1
Maodie Wang 1
Petia Bobadova-Parvanova 2
Quynh Do 2
Zehua Zhou 1
Frank R. Fronczek 1
Kevin M. Smith 1
M. Graça H. Vicente 1
Publication typeJournal Article
Publication date2016-12-30
scimago Q3
wos Q4
SJR0.228
CiteScore1.8
Impact factor0.9
ISSN10884246, 10991409
General Chemistry
Abstract

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.

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GOST |
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GOST Copy
Nguyen A. L. et al. Synthesis and properties ofB-cyano-BODIPYs // Journal of Porphyrins and Phthalocyanines. 2016. Vol. 20. No. 12. pp. 1409-1419.
GOST all authors (up to 50) Copy
Nguyen A. L., Wang M., Bobadova-Parvanova P., Do Q., Zhou Z., Fronczek F. R., Smith K. M., Vicente M. G. H. Synthesis and properties ofB-cyano-BODIPYs // Journal of Porphyrins and Phthalocyanines. 2016. Vol. 20. No. 12. pp. 1409-1419.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1142/s108842461650125x
UR - https://doi.org/10.1142/s108842461650125x
TI - Synthesis and properties ofB-cyano-BODIPYs
T2 - Journal of Porphyrins and Phthalocyanines
AU - Nguyen, Alex L.
AU - Wang, Maodie
AU - Bobadova-Parvanova, Petia
AU - Do, Quynh
AU - Zhou, Zehua
AU - Fronczek, Frank R.
AU - Smith, Kevin M.
AU - Vicente, M. Graça H.
PY - 2016
DA - 2016/12/30
PB - World Scientific
SP - 1409-1419
IS - 12
VL - 20
SN - 1088-4246
SN - 1099-1409
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2016_Nguyen,
author = {Alex L. Nguyen and Maodie Wang and Petia Bobadova-Parvanova and Quynh Do and Zehua Zhou and Frank R. Fronczek and Kevin M. Smith and M. Graça H. Vicente},
title = {Synthesis and properties ofB-cyano-BODIPYs},
journal = {Journal of Porphyrins and Phthalocyanines},
year = {2016},
volume = {20},
publisher = {World Scientific},
month = {dec},
url = {https://doi.org/10.1142/s108842461650125x},
number = {12},
pages = {1409--1419},
doi = {10.1142/s108842461650125x}
}
MLA
Cite this
MLA Copy
Nguyen, Alex L., et al. “Synthesis and properties ofB-cyano-BODIPYs.” Journal of Porphyrins and Phthalocyanines, vol. 20, no. 12, Dec. 2016, pp. 1409-1419. https://doi.org/10.1142/s108842461650125x.