A study on photophysical and photodynamic properties of donor–acceptor BODIPY complexes: Correlation between singlet oxygen quantum yield and singlet-triplet energy gap

Jae Moon Lee; Seongsoo Kang; Tae Gyu Hwang; Hong Mo Kim; Woo Sung Lee; Dongho Kim; Jae Pil Kim

doi:10.1016/j.dyepig.2020.109051

A study on photophysical and photodynamic properties of donor–acceptor BODIPY complexes: Correlation between singlet oxygen quantum yield and singlet-triplet energy gap

Jae Moon Lee, Seongsoo Kang, Tae Gyu Hwang, Hong Mo Kim, Woo Sung Lee, Dongho Kim, Jae Pil Kim

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

Donor–acceptor (D–A) triplet photosensitizers have gained considerable attention in the field of photodynamic therapy. While numerous studies have been conducted on these photosensitizers, their energy transfer mechanism has not been completely elucidated. Herein, we prepared BODIPY-based D–A complexes (AM2–4) to investigate their photophysical and solvatochromic properties. In addition, the hypothesis that a decrease in the singlet and triplet energy gap (ΔE_ST) can increase the intersystem crossing rate and singlet oxygen quantum yield (SOQY) was investigated. Moreover, by designing the experiments under more controlled conditions than those reported in previous studies, we obtained more accurate data. AM2–4 materials with the charge-transfer (CT) character exhibited higher SOQY (0.32–0.44) than AM1 without the CT character. Besides, as the electron-accepting power of the photosensitizers increased, ΔE_ST between the first singlet excited state and triplet excited state decreased, resulting in an increased SOQY. This study elucidates the molecular mechanism of D–A triplet photosensitizers and contributes to the development of efficient photosensitizers for photodynamic therapy.

Original language	English
Article number	109051
Journal	Dyes and Pigments
Volume	187
DOIs	https://doi.org/10.1016/j.dyepig.2020.109051
Publication status	Published - 2021 Mar

Bibliographical note

Funding Information:
This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through Advanced Production Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) [117017]. The authors thank H.-N.Bae of the National Center for Inter-university Research Facilities for assistance with the NMR experiments. We would like to thank Editage (www.editage.co.kr) for English language editing.

Funding Information:
This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through Advanced Production Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) [ 117017 ]. The authors thank H.-N.Bae of the National Center for Inter-university Research Facilities for assistance with the NMR experiments. We would like to thank Editage ( www.editage.co.kr ) for English language editing.

Publisher Copyright:
© 2020

All Science Journal Classification (ASJC) codes

Chemical Engineering(all)
Process Chemistry and Technology

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10.1016/j.dyepig.2020.109051

Cite this

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title = "A study on photophysical and photodynamic properties of donor–acceptor BODIPY complexes: Correlation between singlet oxygen quantum yield and singlet-triplet energy gap",

abstract = "Donor–acceptor (D–A) triplet photosensitizers have gained considerable attention in the field of photodynamic therapy. While numerous studies have been conducted on these photosensitizers, their energy transfer mechanism has not been completely elucidated. Herein, we prepared BODIPY-based D–A complexes (AM2–4) to investigate their photophysical and solvatochromic properties. In addition, the hypothesis that a decrease in the singlet and triplet energy gap (ΔEST) can increase the intersystem crossing rate and singlet oxygen quantum yield (SOQY) was investigated. Moreover, by designing the experiments under more controlled conditions than those reported in previous studies, we obtained more accurate data. AM2–4 materials with the charge-transfer (CT) character exhibited higher SOQY (0.32–0.44) than AM1 without the CT character. Besides, as the electron-accepting power of the photosensitizers increased, ΔEST between the first singlet excited state and triplet excited state decreased, resulting in an increased SOQY. This study elucidates the molecular mechanism of D–A triplet photosensitizers and contributes to the development of efficient photosensitizers for photodynamic therapy.",

author = "Lee, {Jae Moon} and Seongsoo Kang and Hwang, {Tae Gyu} and Kim, {Hong Mo} and Lee, {Woo Sung} and Dongho Kim and Kim, {Jae Pil}",

note = "Funding Information: This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through Advanced Production Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) [117017]. The authors thank H.-N.Bae of the National Center for Inter-university Research Facilities for assistance with the NMR experiments. We would like to thank Editage (www.editage.co.kr) for English language editing. Funding Information: This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through Advanced Production Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) [ 117017 ]. The authors thank H.-N.Bae of the National Center for Inter-university Research Facilities for assistance with the NMR experiments. We would like to thank Editage ( www.editage.co.kr ) for English language editing. Publisher Copyright: {\textcopyright} 2020",

year = "2021",

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doi = "10.1016/j.dyepig.2020.109051",

language = "English",

volume = "187",

journal = "Dyes and Pigments",

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T2 - Correlation between singlet oxygen quantum yield and singlet-triplet energy gap

AU - Lee, Jae Moon

AU - Kang, Seongsoo

AU - Hwang, Tae Gyu

AU - Kim, Hong Mo

AU - Lee, Woo Sung

AU - Kim, Dongho

AU - Kim, Jae Pil

N1 - Funding Information: This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through Advanced Production Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) [117017]. The authors thank H.-N.Bae of the National Center for Inter-university Research Facilities for assistance with the NMR experiments. We would like to thank Editage (www.editage.co.kr) for English language editing. Funding Information: This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through Advanced Production Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) [ 117017 ]. The authors thank H.-N.Bae of the National Center for Inter-university Research Facilities for assistance with the NMR experiments. We would like to thank Editage ( www.editage.co.kr ) for English language editing. Publisher Copyright: © 2020

PY - 2021/3

Y1 - 2021/3

N2 - Donor–acceptor (D–A) triplet photosensitizers have gained considerable attention in the field of photodynamic therapy. While numerous studies have been conducted on these photosensitizers, their energy transfer mechanism has not been completely elucidated. Herein, we prepared BODIPY-based D–A complexes (AM2–4) to investigate their photophysical and solvatochromic properties. In addition, the hypothesis that a decrease in the singlet and triplet energy gap (ΔEST) can increase the intersystem crossing rate and singlet oxygen quantum yield (SOQY) was investigated. Moreover, by designing the experiments under more controlled conditions than those reported in previous studies, we obtained more accurate data. AM2–4 materials with the charge-transfer (CT) character exhibited higher SOQY (0.32–0.44) than AM1 without the CT character. Besides, as the electron-accepting power of the photosensitizers increased, ΔEST between the first singlet excited state and triplet excited state decreased, resulting in an increased SOQY. This study elucidates the molecular mechanism of D–A triplet photosensitizers and contributes to the development of efficient photosensitizers for photodynamic therapy.

AB - Donor–acceptor (D–A) triplet photosensitizers have gained considerable attention in the field of photodynamic therapy. While numerous studies have been conducted on these photosensitizers, their energy transfer mechanism has not been completely elucidated. Herein, we prepared BODIPY-based D–A complexes (AM2–4) to investigate their photophysical and solvatochromic properties. In addition, the hypothesis that a decrease in the singlet and triplet energy gap (ΔEST) can increase the intersystem crossing rate and singlet oxygen quantum yield (SOQY) was investigated. Moreover, by designing the experiments under more controlled conditions than those reported in previous studies, we obtained more accurate data. AM2–4 materials with the charge-transfer (CT) character exhibited higher SOQY (0.32–0.44) than AM1 without the CT character. Besides, as the electron-accepting power of the photosensitizers increased, ΔEST between the first singlet excited state and triplet excited state decreased, resulting in an increased SOQY. This study elucidates the molecular mechanism of D–A triplet photosensitizers and contributes to the development of efficient photosensitizers for photodynamic therapy.

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VL - 187

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 109051

ER -

A study on photophysical and photodynamic properties of donor–acceptor BODIPY complexes: Correlation between singlet oxygen quantum yield and singlet-triplet energy gap

Abstract

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