4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications
Тип публикации: Journal Article
Дата публикации: 2023-04-07
SCImago Q1
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SJR: 1.007
CiteScore: 8.7
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ISSN: 15237060, 15237052
PubMed ID:
37026858
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
The presence of F or CN substituents at boron in BODIPYs causes a dramatic effect on their reactivity, which allows their chemoselective postfunctionalization. Thus, whereas 1,3,5,7-tetramethyl B(CN)2-BODIPYs displayed enhanced reactivity in Knoevenagel condensations with aldehydes, the corresponding BF2-BODIPYs can experience selective aromatic electrophilic substitution (SEAr) reactions in the presence of the former. These (selective) reactions have been employed in the preparation of BODIPY dimers and tetramers, with balanced fluorescence and singlet oxygen formation, and all-BODIPY trimers and heptamers, with potential application as light-harvesting systems.
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Ventura J. et al. 4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications // Organic Letters. 2023. Vol. 25. No. 15. pp. 2588-2593.
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Ventura J., Ventura J., Uriel C., Gómez A. M., Avellanal Zaballa E., Bañuelos J., Solano E., Garcia-Moreno I., García Moreno I., López J. 4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications // Organic Letters. 2023. Vol. 25. No. 15. pp. 2588-2593.
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TY - JOUR
DO - 10.1021/acs.orglett.3c00476
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c00476
TI - 4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications
T2 - Organic Letters
AU - Ventura, Juan
AU - Ventura, J.
AU - Uriel, Clara
AU - Gómez, Ana M
AU - Avellanal Zaballa, Edurne
AU - Bañuelos, Jorge
AU - Solano, Eduardo
AU - Garcia-Moreno, Inmaculada
AU - García Moreno, Inmaculada
AU - López, J.Cristóbal
PY - 2023
DA - 2023/04/07
PB - American Chemical Society (ACS)
SP - 2588-2593
IS - 15
VL - 25
PMID - 37026858
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2023_Ventura,
author = {Juan Ventura and J. Ventura and Clara Uriel and Ana M Gómez and Edurne Avellanal Zaballa and Jorge Bañuelos and Eduardo Solano and Inmaculada Garcia-Moreno and Inmaculada García Moreno and J.Cristóbal López},
title = {4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c00476},
number = {15},
pages = {2588--2593},
doi = {10.1021/acs.orglett.3c00476}
}
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Ventura, Juan, et al. “4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications.” Organic Letters, vol. 25, no. 15, Apr. 2023, pp. 2588-2593. https://pubs.acs.org/doi/10.1021/acs.orglett.3c00476.
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