Journal of Organic Chemistry, volume 76, issue 24, pages 9988-9996
Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
Publication type: Journal Article
Publication date: 2011-11-23
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Halogenated BODIPYs are important synthetic precursors and potential sensitizers for photodynamic therapy (PDT). Electrophilic bromination of pyrrolic-unsubstituted BODIPYs using bromine regioselectively generated mono- to heptabromoBODIPYs in a stepwise fashion in good to excellent yields. These resultant bromoBODIPYs were applied for regioselective substitution and Suzuki coupling reaction to generate BODIPYs 4, 5, 6, and 7 in good to excellent yields. According to NMR and X-ray analysis results, the stepwise bromination first takes place at 2,6-, then at 3,5-, and eventually at 1,7-positions, whereas the regioselective substitution occurs first at 3,5- then at 1,7-positions of the chromophore. The spectroscopic properties of these resultant BODIPYs were studied, which shows the potential application of these bromoBODIPYs as sensitizers for PDT.
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Jiao L. et al. Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes // Journal of Organic Chemistry. 2011. Vol. 76. No. 24. pp. 9988-9996.
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Jiao L., Pang W., Zhou J., Wei Y., Mu X., Bai G., Hao E. Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes // Journal of Organic Chemistry. 2011. Vol. 76. No. 24. pp. 9988-9996.
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TY - JOUR
DO - 10.1021/jo201754m
UR - https://doi.org/10.1021%2Fjo201754m
TI - Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
T2 - Journal of Organic Chemistry
AU - Pang, Weidong
AU - Zhou, Jinyuan
AU - Mu, Xiaolong
AU - Bai, Guifeng
AU - Jiao, Lijuan
AU - Wei, Yun
AU - Hao, Erhong
PY - 2011
DA - 2011/11/23 00:00:00
PB - American Chemical Society (ACS)
SP - 9988-9996
IS - 24
VL - 76
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2011_Jiao,
author = {Weidong Pang and Jinyuan Zhou and Xiaolong Mu and Guifeng Bai and Lijuan Jiao and Yun Wei and Erhong Hao},
title = {Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021%2Fjo201754m},
number = {24},
pages = {9988--9996},
doi = {10.1021/jo201754m}
}
Cite this
MLA
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Jiao, Lijuan, et al. “Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes.” Journal of Organic Chemistry, vol. 76, no. 24, Nov. 2011, pp. 9988-9996. https://doi.org/10.1021%2Fjo201754m.