Dyes and Pigments, volume 202, pages 110215
Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II)
Publication type: Journal Article
Publication date: 2022-06-01
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
Unsymmetrically substituted boron(III) and zinc(II) dipyrromethenates were synthesized in high yields, and the physico-chemical investigation results of them are presented. Comparative analysis of luminescence properties in a series of various organic solvents , photo- and thermal stability was carried out depending on the molecular structure. For the first time it was established that the methyl group absence in α-, β- or β′-position of one of the pyrrole fragments changes properties of pentamethyl-dipyrromethene ligands and complexes differently. It is shown unsubstituted α- or β-position of one pyrrole cycle leads to a hypsochromic shift of the maximum of the intense absorption band and free β′-position – to bathochromic shift. In the general case, the fluorescence quantum yield of BODIPY reaches 99% and depends little on the solvent properties. However, BODIPY unsubstituted in one of the α-position showed a sharp decrease of the fluorescence quantum yield upon going from non-polar solvents to polar. Unsymmetrically substituted zinc(II) dipyrromethenates are characterized by low value of the fluorescence quantum yield, the fluorescence almost completely quenching in weakly polar and polar solvents . It is found that the unsymmetrically substitution increases photostability of boron(III) and zinc(II) complexes but decreases their thermal stability in solid state. • Unsymmetrically substituted dipyrromethenes and their complexes are synthesized. • Zinc complexes are more sensitive to solvent properties than BODIPY. • BODIPY fluorescence quantum yield is higher than that of zinc complexes. • Photo and thermal stability of the complexes change antibatically. • To explain the properties of the compounds, DFT calculations were carried out.
Citations by journals
|
1
2
|
|
|
Journal of Molecular Liquids
|
Journal of Molecular Liquids
2 publications, 50%
|
|
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
|
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
1 publication, 25%
|
|
Journal of Luminescence
|
Journal of Luminescence
1 publication, 25%
|
|
1
2
|
Citations by publishers
|
1
2
3
4
|
|
|
Elsevier
|
Elsevier
4 publications, 100%
|
|
1
2
3
4
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2023,2024],"ids":[0,0],"codes":[0,0],"imageUrls":["",""],"datasets":[{"label":"Citations number","data":[1,3],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":["25","75"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Journal of Molecular Liquids","Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy","Journal of Luminescence"],"ids":[13597,6337,7075],"codes":[0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp"],"datasets":[{"label":"","data":[2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":[50,25,25],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Elsevier"],"ids":[17],"codes":[0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp"],"datasets":[{"label":"","data":[4],"backgroundColor":["#3B82F6"],"percentage":[100],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex
Cite this
GOST
Copy
Berezin M. B. et al. Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II) // Dyes and Pigments. 2022. Vol. 202. p. 110215.
GOST all authors (up to 50)
Copy
Berezin M. B., Dogadaeva S. A., Antina E. V., Lukanov M. M., Ksenofontov A. A., Semeikin A. A. Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II) // Dyes and Pigments. 2022. Vol. 202. p. 110215.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.dyepig.2022.110215
UR - https://doi.org/10.1016%2Fj.dyepig.2022.110215
TI - Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II)
T2 - Dyes and Pigments
AU - Berezin, Mikhail B
AU - Dogadaeva, Sofya A
AU - Antina, Elena V
AU - Lukanov, M. M.
AU - Ksenofontov, Alexander A
AU - Semeikin, Alexander A
PY - 2022
DA - 2022/06/01 00:00:00
PB - Elsevier
SP - 110215
VL - 202
SN - 0143-7208
SN - 1873-3743
ER -
Cite this
BibTex
Copy
@article{2022_Berezin,
author = {Mikhail B Berezin and Sofya A Dogadaeva and Elena V Antina and M. M. Lukanov and Alexander A Ksenofontov and Alexander A Semeikin},
title = {Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II)},
journal = {Dyes and Pigments},
year = {2022},
volume = {202},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016%2Fj.dyepig.2022.110215},
pages = {110215},
doi = {10.1016/j.dyepig.2022.110215}
}