Journal of Fluorescence, volume 29, issue 4, pages 911-920

Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes

Publication typeJournal Article
Publication date2019-06-26
Quartile SCImago
Q1
Quartile WOS
Q3
Impact factor2.7
ISSN10530509, 15734994
Biochemistry
Spectroscopy
Clinical Biochemistry
Law
Sociology and Political Science
Social Sciences (miscellaneous)
Clinical Psychology
Abstract
Boron(III) complexes with alkyl-, phenyl-, and halogen-substituted 2,2′-dipyrromethenes (BODIPY) and meso-aza-dipyrrometenes (ms-aza-BODIPY) were synthesized. The structure relationship of the obtained coordination compounds with their luminescent characteristics is analyzed. Arylated BODIPY, in contrast to alkyl-substituted analogs, is more sensitive to interparticle interactions with a solvent, causing a decrease in the quantum yield by up to 40%. The introduction of phenyl substituents into the BODIPY molecule shifts the first absorption band bathochromic, significantly (32–37 nm) increases the Stokes shift in the emission spectrum, but reduces the probability of the S0 → S1 electronic transition as compared to alkylated complexes. Replacing the methine carbon atom with nitrogen leads to quenching of ms-aza-BODIPY fluorescence compared to BODIPY up to 5–20%. The stability of 2,2′-dipyrromethenes difluoroborates to oxidative destruction under the influence of UV irradiation in cyclohexane solutions was evaluated. It has been shown that symmetric aryl substitution in pyrrole cycles of dipyrromethene significantly increases the photostability of the corresponding compounds as compared to alkyl-substituted analogs and is an effective method of obtaining boron (III) dipyrromethenates with practically useful properties. It has been established that the replacement of the methin ms-spacer of dipyrromethene by a nitrogen atom significantly reduces the photostability of ms-aza-dipyrromethenates of boron. Halogenation of β-positions of pyrrole cycles by a factor of 5–8 reduces the photostability of difluoroborates ms-aza-dipyrromethenes in comparison with a non-halogenated analogue.

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Kritskaya A. Yu. et al. Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes // Journal of Fluorescence. 2019. Vol. 29. No. 4. pp. 911-920.
GOST all authors (up to 50) Copy
Kritskaya A. Yu., Berezin M. B., Antina E. V., Vyugin A. I. Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes // Journal of Fluorescence. 2019. Vol. 29. No. 4. pp. 911-920.
RIS |
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TY - JOUR
DO - 10.1007/s10895-019-02403-2
UR - https://doi.org/10.1007%2Fs10895-019-02403-2
TI - Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes
T2 - Journal of Fluorescence
AU - Kritskaya, Anna Yu
AU - Berezin, Mikhail B
AU - Vyugin, Anatoly I.
AU - Antina, Elena V.
PY - 2019
DA - 2019/06/26 00:00:00
PB - Springer Nature
SP - 911-920
IS - 4
VL - 29
SN - 1053-0509
SN - 1573-4994
ER -
BibTex |
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BibTex Copy
@article{2019_Kritskaya
author = {Anna Yu Kritskaya and Mikhail B Berezin and Anatoly I. Vyugin and Elena V. Antina},
title = {Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes},
journal = {Journal of Fluorescence},
year = {2019},
volume = {29},
publisher = {Springer Nature},
month = {jun},
url = {https://doi.org/10.1007%2Fs10895-019-02403-2},
number = {4},
pages = {911--920},
doi = {10.1007/s10895-019-02403-2}
}
MLA
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Kritskaya, Anna Yu., et al. “Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes.” Journal of Fluorescence, vol. 29, no. 4, Jun. 2019, pp. 911-920. https://doi.org/10.1007%2Fs10895-019-02403-2.
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