Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation

被引：8
作者：
Zuo, Huiquan [1 ,2 ,3 ]
Wu, Qinghua [5 ]
Guo, Xing [1 ,2 ,3 ]
Kang, Zhengxin [4 ]
Gao, Jiangang [4 ]
Wei, Ying [1 ,2 ,3 ]
Yu, Changjiang [1 ,2 ,3 ]
Jiao, Lijuan [1 ,2 ,3 ]
Hao, Erhong [1 ,2 ,3 ]
机构：
[1] Anhui Lab Mol Based Mat, Wuhu 241002, Peoples R China
[2] Minist Educ, Key Lab Funct Mol Solids, Wuhu 241002, Peoples R China
[3] Anhui Normal Univ, Sch Chem & Mat Sci, Wuhu 241002, Peoples R China
[4] Anhui Polytech Univ, Sch Chem & Environm Engn, Wuhu 241000, Anhui, Peoples R China
[5] Anhui Univ Chinese Med, Sch Pharm, Hefei 230012, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 45期
基金：
中国国家自然科学基金;
关键词：
DYES; FUNCTIONALIZATION; STABILITY; DESIGN;
D O I：
10.1021/acs.orglett.3c03330
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 alpha-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.
引用
收藏
页码：8150 / 8155
页数：6
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