Citation: Si-Fu Gao, Qiang-Qiang Li, Xing Li, Zi-Qiang Zhang, Huanan Huang, Jun Xuan. Rational design of phenanthridine-based AIEgens for organelle-specific imaging: A dual-functional strategy via free amine modulation and carbon-insertion π-extension[J]. Chinese Chemical Letters, ;2026, 37(6): 111519. doi: 10.1016/j.cclet.2025.111519 shu

Rational design of phenanthridine-based AIEgens for organelle-specific imaging: A dual-functional strategy via free amine modulation and carbon-insertion π-extension

Si-Fu Gao ^a ,
Qiang-Qiang Li ^{a, *,} ,
Xing Li ^a ,
Zi-Qiang Zhang ^a ,
Huanan Huang ^{b, *,} ,
Jun Xuan ^{a, c, *,}

a.
Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei 230601, China
b.
College of Chemistry and Chemical Engineering, Jiangxi Province Engineering Research Center of Ecological Chemical Industry, Jiujiang Key Laboratory of Organosilicon Chemistry and Application, Xinghuo Organosilicon Industry Research Center, Jiujiang University, Jiujiang 332005, China
c.
Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University), Ministry of Education, Hefei 230601, China

liqiangqiang@ahu.edu.cn

huanan200890@163.com

xuanjun@ahu.edu.cn

Received Date: 29 April 2025
Revised Date: 25 June 2025
Accepted Date: 26 June 2025
Available Online: 27 June 2025

Figures(5)

Phenanthridine-based luminogens are known for their exceptional opto-electronic properties. They have been used in fluorescent materials as well as in biological fields. However, traditional methods for constructing the phenanthridine scaffold typically require pre-functionalized starting materials, photosensitizers or noble transition metals, which will complicate the synthesis and increase the cost. In this study, we introduce an efficient and metal-free approach to synthesize the phenanthridine derivates from free amines under visible-light irradiation. The phenanthridine ring is formed through a carbon insertion π-extension strategy. Significantly, rational design of the leaving group for the carbon-insertion reactions plays a crucial role. We successfully synthesized phenanthridine-based luminogens (DPA-Phen, MeO-DPA-Phen, and DMA-DPA-Phen). These luminogens display robust aggregation-induced emission (AIE) characteristics. Notably, they selectively localize within the lipid droplets (LDs) of tumor cells, demonstrating the potential of phenanthridine-based frameworks as viable LDs-selective fluorescent probes.
- Visible-light irradiation,
- Carbon-insertion,
- Phenanthridine luminogens,
- Aggregation-induced emission,
- Fluorescent imaging
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