American Chemical Society (ACS)
Organic Letters
,  volume 25 ,  issue 15 ,  pages 2588-2593

4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications

Publication type: Journal Article
Publication date: 2023-04-07
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
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BibTex (up to 50 authors) Copy
@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}
}
MLA
Cite this
MLA Copy
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.