大学化学 >> 2026, Vol. 41 >> Issue (5): 109-119.doi: 10.12461/PKU.DXHX202511066

所属专题： 第5届全国大学生化学实验创新设计大赛

专题 上一篇    

聚光成辉——Suzuki偶联反应高效制备聚集诱导发射荧光分子及其潜指纹识别应用

朱森强, 李若涵, 杨雨佳, 廖金志, 刘睿   

  1. 南京工业大学化学与分子工程学院, 江苏 南京 211816
  • 收稿日期:2025-11-13 录用日期:2026-02-27 发布日期:2026-05-21
  • 通讯作者: 刘睿 E-mail:rui.liu@njtech.edu.cn Rui Liu
  • 基金资助:
    南京工业大学高等教育教学改革研究课题(20250144)；南京工业大学本科课程思政示范课程建设项目(20240031)

Gather the light into glory: efficient preparation of aggregation induced emission fluorescent molecules by Suzuki coupling reaction for latent fingerprint detection

Senqiang Zhu, Ruohan Li, Yujia Yang, Jinzhi Liao, Rui Liu   

  1. School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, Jiangsu Province, China
  • Received:2025-11-13 Accepted:2026-02-27 Published:2026-05-21
  • Contact: Rui Liu E-mail:rui.liu@njtech.edu.cn

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摘要： 本实验基于Suzuki偶联反应，以4-三苯胺硼酸和5-溴-2-羧基噻吩为原料，经加热、回流、过滤、萃取、干燥等单元操作，合成了5-(4-(二苯胺)苯基)噻吩-2-羧酸钾(TTC)，并利用核磁氢谱、紫外-可见吸收光谱、荧光发射光谱对该物质的结构及光物理性质进行了系统的研究。实验结果表明，所合成分子表现出高效的蓝光发射及显著的聚集诱导发光(AIE)性质。基于此，本实验以荧光功能分子的实际应用为导向，设计了潜指纹检测成像的实验环节。该有机荧光分子可作为指纹显影剂，快速高效地实现高质量指纹图像显影和三级指纹特征检测，并通过MATLAB指纹识别系统对提取的指纹进行对比。该实验实现了化学合成-材料表征-应用探索的教学闭环。经推广，该实验现象明显，重复性好，展示度高，有利于激发学生学习兴趣。通过实验训练，学生不仅掌握交叉学科知识，更建立起“分子设计-性能调控-功能应用”的系统研究思维，为培养创新性人才提供了优质的实践平台。

关键词: Suzuki偶联反应, 聚集诱导发光, 潜指纹识别, 功能材料

Abstract: This study employed Suzuki coupling reaction to synthesize potassium 5-(4-(diphenylamino)phenyl)thiophene-2-carboxylate (TTC) from 4-triphenylamineboronic acid and 5-bromo-2-carboxythiophene through a series of unit operations including heating, refluxing, filtration, extraction, and drying. The molecular structure and photophysical properties of TTC were systematically characterized using 1H nuclear magnetic resonance (NMR) spectroscopy, UV-vis absorption spectroscopy, and fluorescence emission spectroscopy. Results demonstrate that the synthesized compound exhibits efficient blue-light emission and remarkable aggregation-induced emission (AIE) characteristics. Building upon these findings, we developed a practical application by designing a latent fingerprint detection protocol. The organic fluorophore serves as an effective fingerprint developer, enabling rapid visualization of high-quality fingerprint images with clear tertiary ridge characteristics. Fingerprint matching was performed using MATLAB-based recognition system. This experiment establishes a complete pedagogical framework encompassing chemical synthesis, material characterization, and application exploration. Preliminary implementation shows excellent experimental reproducibility with visually striking results, effectively stimulating student interest. Through this comprehensive training, students not only acquire interdisciplinary knowledge, but also develop systematic research thinking spanning molecular design, property modulation, and functional applications, while mastering essential techniques in organic synthesis, photophysical characterization, spectral analysis, and fingerprint development.

Key words: Suzuki coupling reaction, Aggregation-induced emission, Latent fingerprint detection, Functional materials