Citation: Limin He, Xiaomao Zhou, Yongli Zhang, Luyan Tian, Yanqing Li, Yunxia Zhao, Shulin Gao, Yanni Li, Yanhua Yang, Weili Li, Xiangguang Li, Wei Fan, Wei Jiang, Zhaohui Wang. NIR fluorescent benzofuran-fused oligo-BODIPY dyes: Synthesis, characteristics and tunable electrochemical properties[J]. Chinese Chemical Letters, ;2026, 37(12): 112693. doi: 10.1016/j.cclet.2026.112693 shu

NIR fluorescent benzofuran-fused oligo-BODIPY dyes: Synthesis, characteristics and tunable electrochemical properties

Limin He ^a ,
Xiaomao Zhou ^a ,
Yongli Zhang ^a ,
Luyan Tian ^a ,
Yanqing Li ^a ,
Yunxia Zhao ^a ,
Shulin Gao ^a ,
Yanni Li ^a ,
Yanhua Yang ^a ,
Weili Li ^a ,
Xiangguang Li ^{a, *,} ,
Wei Fan ^{b, *,} ,
Wei Jiang ^{c, *,} ,
Zhaohui Wang ^d

a.
Yunnan Key Laboratory of Metal-Organic Molecular Materials and Device, School of Chemistry and Chemical Engineering, Kunming University, Kunming 650214, China
b.
School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China
c.
School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
d.
Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, China

lixiangguang@iccas.ac.cn

fanwei25@bit.edu.cn

jiangw@ucas.ac.cn

Received Date: 14 January 2026
Revised Date: 26 March 2026
Accepted Date: 27 March 2026
Available Online: 28 March 2026

Figures(6)

Large π-conjugated systems are promising near-infrared (NIR) fluorophores but are often limited by synthetic complexity and compromised luminescence efficiency. Herein, we report the first synthesis of benzofuran-fused oligo-boron-dipyrromethene (BODIPY) dyes via a synergistic combination of S_NAr and C–H coupling strategy. This modular strategy enables efficient construction of mono-, bis-, and fully fused oligomeric architectures. Progressive benzofuran and BODIPY fusion induces pronounced bathochromic shifts and markedly enhanced molar extinction coefficients. The fully fused trimer BFB-tri exhibits strong NIR absorption (716 nm in toluene, ε = 4.0 × 10⁵ L mol⁻¹ cm⁻¹) and bright NIR emission (733/808 nm) with a fluorescence quantum yield up to 65.4%. Experimental and theoretical studies reveal that benzofuran fusion raises the highest occupied molecular orbital (HOMO) level, while increasing BODIPY units lowers the lowest unoccupied molecular orbital (LUMO), allowing precise frontier orbital modulation for rational design of π-extended NIR fluorophores.
- NIR fluorescent dyes,
- Oligo-BODIPY,
- Fluorescence quantum yield,
- Structure modification,
- Heterocyclic
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