Open Access
International Journal of Molecular Sciences, volume 22, issue 13, pages 6735
Photochemical Properties and Stability of BODIPY Dyes
Smolarkiewicz Wyczachowski Aleksander
1
,
Piskorz Jaroslaw
2
,
Bocian Szymon
1
,
Ziegler Borowska Marta
1
,
Kędziera Dariusz
1
,
1
Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina 7, 87-100 Toruń, Poland
|
2
Department of Inorganic and Analytical Chemistry, University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland
|
Publication type: Journal Article
Publication date: 2021-06-23
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.6
ISSN: 16616596, 14220067
PubMed ID:
34201648
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Computer Science Applications
Spectroscopy
Molecular Biology
General Medicine
Abstract
The present study is devoted to the combined experimental and theoretical description of the photophysical properties and photodegradation of the new boron-dipyrromethene (BODIPY) derivatives obtained recently for biomedical applications, such as bacteria photoinactivation (Piskorz et al., Dyes and Pigments 2020, 178, 108322). Absorption and emission spectra for a wide group of solvents of different properties for the analyzed BODIPY derivatives were investigated in order to verify their suitability for photopharmacological applications. Additionally, the photostability of the analyzed systems were thoroughly determined. The exposition to the UV light was found first to cause the decrease in the most intensive absorption band and the appearance of the hypsochromically shifted band of similar intensity. On the basis of the chromatographic and computational study, this effect was assigned to the detachment of the iodine atoms from the BODIPY core. After longer exposition to UV light, photodegradation occurred, leading to the disappearance of the intensive absorption bands and the emergence of small intensity signals in the strongly blue-shifted range of the spectrum. Since the most intensive bands in original dyes are ascribed to the molecular core bearing the BF2 moiety, this result can be attributed to the significant cleavage of the BF2 ring. In order to fully characterize the obtained molecules, the comprehensive computational chemistry study was performed. The influence of the intermolecular interactions for their absorption in solution was analyzed. The theoretical data entirely support the experimental outcomes.
Citations by journals
|
1
2
|
|
|
Journal of Photochemistry and Photobiology A: Chemistry
|
Journal of Photochemistry and Photobiology A: Chemistry
2 publications, 11.76%
|
|
Polyhedron
|
Polyhedron
1 publication, 5.88%
|
|
Tetrahedron
|
Tetrahedron
1 publication, 5.88%
|
|
Angewandte Chemie
|
Angewandte Chemie
1 publication, 5.88%
|
|
Angewandte Chemie - International Edition
|
Angewandte Chemie - International Edition
1 publication, 5.88%
|
|
ACS Omega
|
ACS Omega
1 publication, 5.88%
|
|
Photonics
|
Photonics
1 publication, 5.88%
|
|
Journal of Molecular Structure
|
Journal of Molecular Structure
1 publication, 5.88%
|
|
Industrial & Engineering Chemistry Research
|
Industrial & Engineering Chemistry Research
1 publication, 5.88%
|
|
Polymer
|
Polymer
1 publication, 5.88%
|
|
Biomedicine and Pharmacotherapy
|
Biomedicine and Pharmacotherapy
1 publication, 5.88%
|
|
Biomolecules
|
Biomolecules
1 publication, 5.88%
|
|
New Journal of Chemistry
|
New Journal of Chemistry
1 publication, 5.88%
|
|
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
|
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
1 publication, 5.88%
|
|
ACS Catalysis
|
ACS Catalysis
1 publication, 5.88%
|
|
Inorganic Chemistry Frontiers
|
Inorganic Chemistry Frontiers
1 publication, 5.88%
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
6
7
8
|
|
|
Elsevier
|
Elsevier
8 publications, 47.06%
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
3 publications, 17.65%
|
|
Wiley
|
Wiley
2 publications, 11.76%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 11.76%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
2 publications, 11.76%
|
|
1
2
3
4
5
6
7
8
|
- 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":[2022,2023,2024],"ids":[0,0,0],"codes":[0,0,0],"imageUrls":["","",""],"datasets":[{"label":"Citations number","data":[5,9,3],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":["29.41","52.94","17.65"],"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 Photochemistry and Photobiology A: Chemistry","Polyhedron","Tetrahedron","Angewandte Chemie","Angewandte Chemie - International Edition","ACS Omega","Photonics","Journal of Molecular Structure","Industrial & Engineering Chemistry Research","Polymer","Biomedicine and Pharmacotherapy","Biomolecules","New Journal of Chemistry","Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy","ACS Catalysis","Inorganic Chemistry Frontiers"],"ids":[18164,21269,3439,25450,19215,18901,12741,9347,12141,19955,23951,13780,1404,6337,4873,8397],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[11.76,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88,5.88],"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","American Chemical Society (ACS)","Wiley","Multidisciplinary Digital Publishing Institute (MDPI)","Royal Society of Chemistry (RSC)"],"ids":[17,40,11,202,123],"codes":[0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[8,3,2,2,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[47.06,17.65,11.76,11.76,11.76],"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 |
MLA
Cite this
GOST
Copy
Rybczyński P. et al. Photochemical Properties and Stability of BODIPY Dyes // International Journal of Molecular Sciences. 2021. Vol. 22. No. 13. p. 6735.
GOST all authors (up to 50)
Copy
Rybczyński P., Smolarkiewicz Wyczachowski A., Piskorz J., Bocian S., Ziegler Borowska M., Kędziera D., Kaczmarek-Kędziera A. Photochemical Properties and Stability of BODIPY Dyes // International Journal of Molecular Sciences. 2021. Vol. 22. No. 13. p. 6735.
Cite this
RIS
Copy
TY - JOUR
DO - 10.3390/ijms22136735
UR - https://doi.org/10.3390%2Fijms22136735
TI - Photochemical Properties and Stability of BODIPY Dyes
T2 - International Journal of Molecular Sciences
AU - Piskorz, Jaroslaw
AU - Bocian, Szymon
AU - Rybczyński, Patryk
AU - Smolarkiewicz Wyczachowski, Aleksander
AU - Ziegler Borowska, Marta
AU - Kędziera, Dariusz
AU - Kaczmarek-Kędziera, Anna
PY - 2021
DA - 2021/06/23 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 6735
IS - 13
VL - 22
PMID - 34201648
SN - 1661-6596
SN - 1422-0067
ER -
Cite this
BibTex
Copy
@article{2021_Rybczyński,
author = {Jaroslaw Piskorz and Szymon Bocian and Patryk Rybczyński and Aleksander Smolarkiewicz Wyczachowski and Marta Ziegler Borowska and Dariusz Kędziera and Anna Kaczmarek-Kędziera},
title = {Photochemical Properties and Stability of BODIPY Dyes},
journal = {International Journal of Molecular Sciences},
year = {2021},
volume = {22},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {jun},
url = {https://doi.org/10.3390%2Fijms22136735},
number = {13},
pages = {6735},
doi = {10.3390/ijms22136735}
}
Cite this
MLA
Copy
Rybczyński, Patryk, et al. “Photochemical Properties and Stability of BODIPY Dyes.” International Journal of Molecular Sciences, vol. 22, no. 13, Jun. 2021, p. 6735. https://doi.org/10.3390%2Fijms22136735.