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研究论文

基于四苯乙烯结构的AIE效应有机多晶体合成：分子构象和Cys检测性能研究

张继东*,a, 王浩a, 权校昕a, 张胜海a, 厍伟b   

  1. a安康学院 化学与环境学院 陕西 安康 725000;
    b包头师范学院 化学学院 内蒙古 包头014030
  • 收稿日期:2025-09-17 修回日期:2025-11-21
  • 基金资助:
    陕西省重点研发计划项目(2023YBGY-152),陕西省基础科学研究院科学研究计划项目（23JHQ033）,陕西省教育厅专项科研计划项目(23JK0274),陕西省大学生创新创业训练计划资助项目(S202311397067,S202411397065)

Synthesis of AIE Effect Organic Polymorphs Based on Tetraphenylethene Structure: Research on Molecular Conformation and Detection Performance

Zhang, Jidong*,a, Wang, Haoa, Quan, Xiaoxina, Zhang, shenghaia, She, Weib   

  1. aCollege of Chemistry and Environment, Ankang University,Ankang, Shaanxi 725000;
    bInstitute of Chemistry,Baotou Teachers College,Baotou,Inner Mongolia, 014030
  • Received:2025-09-17 Revised:2025-11-21
  • Contact: *E-mail: akuzjd@aku.edu.cn

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合成了一种具有聚集诱导发光效应（AIE）的基于四苯乙烯2,4-二硝基苯磺酰基衍生物TPE-1。通过荧光发射光谱对 TPE-1的 AIE 性能进行了研究。经过对TPE-1耐心结晶分离,制备出了 TPE-1s 和 TPE-1t 多晶型物。单晶衍射数据用于证明其构效关系。最独特的是TPE单元苯环和2,4-二硝基苯磺酰基单元之间的TPE-1s的扭转角为80.399,而TPE-1t的扭转角为48.956。有趣的是,TPE单元类似螺旋桨样非平面结构可能导致不同分子间相互作用的构象,例如TPE-1s 中C-H∙∙∙π相互作用（3.1097 Å）,而在TPE-1t中C-H∙∙∙π相互作用（2.7640 Å）。由于结构受扭转角的影响,两种晶体中的分子在端位形成不同的排列模式。这些结果推断出分子构象明显影响发光特性,具有略有扭曲的分子构象的晶体比具有严重扭曲的分子构象的发射更强。另外,TPE-1s对半胱氨酸（Cysteine,Cys）在磷酸盐缓冲液(phosphate buffer saline,PBS)中表现出良好的选择性和灵敏性检测,其检出限为 26.7 nmol/L。

关键词: 多晶体, 聚集诱导发光, 荧光探针, 半胱氨酸

A tetraphenylethene based 2, 4-dinitrobenzenesulfonyl derivative TPE-1 with aggregation-induced enhanced emission effect (AIE) was synthesized. The AIE performance of TPE-1 was studied by fluorescence emission spectroscopy. After patient crystallization and separation of TPE-1, TPE-1s and TPE-1t polymorphs were prepared. Single crystal diffraction data were used to prove its structure-activity relationship. The most distinctive feature is that the torsional angle of TPE-1s between the benzene ring of the TPE unit and the 2, 4-dinitrobenzenesulfonyl unit is 80.399, while that of TPE-1t is 48.956. Interestingly, the propeller-like non-planar structure of the TPE unit may lead to conformations of different intermolecular interactions, such as the C-H∙∙∙π interaction in TPE-1s (3.1097 A), and the C-H∙∙∙π interaction in TPE-1t (2.7640 A). Due to the influence of the torsion angle on the structure, the molecules is two crystals form different arrangement patterns at the ends. These results infered that the molecular conformation significantly affects the luminescence characteristics. Crystals with slightly is distorted molecular conformations emit more strongly than those with severely distorted molecular conformations. In addition, TPE-1s demonstrated excellent selectivity and sensitivity in the detection of Cysteine (Cys) in PBS buffer solution, and the detection limit is 26.7 nmol/L.

Key words: polymorphs, aggregation-induced emission (AIE), fluorescence probe, Cysteine