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

页码：8150 / 8155

页数：6

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