Dyes and Pigments, volume 164, pages 139-147
Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction
Publication type: Journal Article
Publication date: 2019-05-01
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
To test the tunability of charge transfer (CT)-based BODIPY photosensitizers in generating singlet oxygen (1Δg), twelve meso-phenyl-BODIPY (donor-acceptor) type compounds have been synthesized and fully characterized, in which the phenyl moiety is modified with respective 0, 1, 2 and 3 methoxy groups to increase its electron-donating ability. The UV-Vis absorption spectra, fluorescence emission spectra, fluorescence quantum yield, fluorescence lifetime, excited triplet state formation, and singlet oxygen formation properties are measured. DFT quantum chemical computation is also carried out to explain the experiments. The occurrence of intra-molecular CT is confirmed by UV-Vis absorption, fluorescence properties and quantum chemical computation. The triplet excited state formation is evidenced by laser flash photolysis technique. The quantitative photosensitized singlet oxygen formation is demonstrated by DPBF (diphenylisobenzofuran) chemical trapping method. This type of BODIPY CT photosensitizers show good tunability in generating singlet oxygen (1Δg). When the number of methoxy group on the donor is increased (so that CT is enhanced), the efficiency of singlet oxygen generation becomes higher from 0.070 to 0.30. When solvent polarity is increased (CT is also enhanced), the efficiency of singlet oxygen generation is also increased significantly. The increase in singlet oxygen generation is accompanied by the decrease in fluorescence quantum yield and fluorescence lifetime values. These facts show that a higher CT efficiency in a simple phenyl-BODIPY donor-acceptor conjugate can lead to significant higher quantum yield of singlet oxygen generation. These results are useful in designing novel CT-based heavy-atom-free photosensitizers for photodynamic therapy of tumor.
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3 publications, 8.11%
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2 publications, 5.41%
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1 publication, 2.7%
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- 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.
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Hu W. et al. Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction // Dyes and Pigments. 2019. Vol. 164. pp. 139-147.
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Hu W., Lin Y., Zhang X., Feng M., Zhao S., Zhang J. Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction // Dyes and Pigments. 2019. Vol. 164. pp. 139-147.
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TY - JOUR
DO - 10.1016/j.dyepig.2019.01.019
UR - https://doi.org/10.1016%2Fj.dyepig.2019.01.019
TI - Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction
T2 - Dyes and Pigments
AU - Hu, Wenbin
AU - Lin, Yanhe
AU - Zhang, Xian-Fu
AU - Feng, Mingna
AU - Zhao, Siwen
AU - Zhang, Jing
PY - 2019
DA - 2019/05/01 00:00:00
PB - Elsevier
SP - 139-147
VL - 164
SN - 0143-7208
SN - 1873-3743
ER -
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@article{2019_Hu,
author = {Wenbin Hu and Yanhe Lin and Xian-Fu Zhang and Mingna Feng and Siwen Zhao and Jing Zhang},
title = {Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction},
journal = {Dyes and Pigments},
year = {2019},
volume = {164},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016%2Fj.dyepig.2019.01.019},
pages = {139--147},
doi = {10.1016/j.dyepig.2019.01.019}
}