Dyes and Pigments, volume 179, pages 108399
Synthesis, spectral and crystal structures of gem-dibromovinyl boron dipyrrins
1
Department of Nuclear Medicine and Radiobiology, Faculty of Medicine and Health Sciences, Université de Sherbrooke, Sherbrooke, Québec J1H5N4, Canada
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2
Department of Nuclear Medicine and Radiobiology, Faculty of Medicine and Health Sciences, Université de Sherbrooke, Sherbrooke, Québec, J1H5N4, Canada
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Publication type: Journal Article
Publication date: 2020-08-01
Journal:
Dyes and Pigments
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.5
ISSN: 01437208, 18733743
General Chemical Engineering
Process Chemistry and Technology
Abstract
A series of BODIPYs (boron-dipyrromethene dyes; 4,4-difluoro-5-aryl-4-bora-3a,4a-diaza-s-indacene) derivatives, bearing an aldehyde group at different pyrrole positions, were transformed into gem-dibromovinyl analogs using the Corey-Fuchs or Lautens olefination method. The gem-dibromovinyl moieties (one or two) are symmetric/asymmetric and attached at α- or β-positions of the pyrrole ring, directly or through the extension of a β-position substituted phenyl spacer ring. The molecular structures of the resultant dyes were assigned using MS, 1H, 13C, 19F NMR, X-ray diffraction and for some compounds 2D HSQC and 11B NMR. The absorption, fluorescence and solvatochromism properties were investigated in different solvents. The highest absorption and emission maxima were obtained for compounds having two gem-dibromovinyl groups attached directly at the α-positions. The best correlation (R-coefficient) of absorption between the solvents and spectral properties of the BODIPYs was obtained using the refractive index of the solvent. The R-coefficient of emission was obtained only for compounds having gem-dibromo vinyl moieties at α-positions. Their solid states clearly reveal distinct patterns of gem-dibromovinyl orientation, torsion angles of the 5-phenyl ring and the indacene plane. Hirshfeld surface analyses were used to visualize various intermolecular interactions.
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Citations by publishers
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Shanghai Institute of Organic Chemistry
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Wiley
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 20%
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Ali H., Guérin B., Van Lier J. Synthesis, spectral and crystal structures of gem-dibromovinyl boron dipyrrins // Dyes and Pigments. 2020. Vol. 179. p. 108399.
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Ali H., Guérin B., Van Lier J. Synthesis, spectral and crystal structures of gem-dibromovinyl boron dipyrrins // Dyes and Pigments. 2020. Vol. 179. p. 108399.
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TY - JOUR
DO - 10.1016/j.dyepig.2020.108399
UR - https://doi.org/10.1016%2Fj.dyepig.2020.108399
TI - Synthesis, spectral and crystal structures of gem-dibromovinyl boron dipyrrins
T2 - Dyes and Pigments
AU - Ali, Hasrat
AU - Guérin, Brigitte
AU - Van Lier, J.
PY - 2020
DA - 2020/08/01 00:00:00
PB - Elsevier
SP - 108399
VL - 179
SN - 0143-7208
SN - 1873-3743
ER -
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@article{2020_Ali,
author = {Hasrat Ali and Brigitte Guérin and J. Van Lier},
title = {Synthesis, spectral and crystal structures of gem-dibromovinyl boron dipyrrins},
journal = {Dyes and Pigments},
year = {2020},
volume = {179},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016%2Fj.dyepig.2020.108399},
pages = {108399},
doi = {10.1016/j.dyepig.2020.108399}
}