Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation
Huiquan Zuo
1
,
Qinghua Wu
2
,
Xing Guo
1
,
Zhengxin Kang
3
,
Jiangang Gao
3
,
Ying Wei
1
,
Changjiang Yu
1
,
Lijuan Jiao
1
,
Publication type: Journal Article
Publication date: 2023-11-03
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
37921615
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Through a strong oxidant Pb(OAc)4 promoted oxidative nucleophilic hydrogen substitution, site-selective direct and stepwise cyanation of BODIPYs using tetrabutylammonium cyanide was developed to give α-cyanated BODIPY derivatives. Characterization of optical and electrochemical properties of these dyes provides substantial enhancement of the electron affinity, with a reduction potential and LUMO level as low as -0.04 V and -4.43 eV, respectively. Radical anions of these electron-deficient 3,5-dicyanated BODIPYs were characterized by absorption and EPR spectroscopy.
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11
Total citations:
11
Citations from 2024:
11
(100%)
The most citing journal
Citations in journal:
1
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MLA
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GOST
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Zuo H. et al. Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation // Organic Letters. 2023. Vol. 25. No. 45. pp. 8150-8155.
GOST all authors (up to 50)
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Zuo H., Wu Q., Guo X., Kang Z., Gao J., Wei Y., Yu C., Jiao L., Hao E. Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation // Organic Letters. 2023. Vol. 25. No. 45. pp. 8150-8155.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.3c03330
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c03330
TI - Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation
T2 - Organic Letters
AU - Zuo, Huiquan
AU - Wu, Qinghua
AU - Guo, Xing
AU - Kang, Zhengxin
AU - Gao, Jiangang
AU - Wei, Ying
AU - Yu, Changjiang
AU - Jiao, Lijuan
AU - Hao, Erhong
PY - 2023
DA - 2023/11/03
PB - American Chemical Society (ACS)
SP - 8150-8155
IS - 45
VL - 25
PMID - 37921615
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2023_Zuo,
author = {Huiquan Zuo and Qinghua Wu and Xing Guo and Zhengxin Kang and Jiangang Gao and Ying Wei and Changjiang Yu and Lijuan Jiao and Erhong Hao},
title = {Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c03330},
number = {45},
pages = {8150--8155},
doi = {10.1021/acs.orglett.3c03330}
}
Cite this
MLA
Copy
Zuo, Huiquan, et al. “Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation.” Organic Letters, vol. 25, no. 45, Nov. 2023, pp. 8150-8155. https://pubs.acs.org/doi/10.1021/acs.orglett.3c03330.
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