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

doi:10.6023/cjoc202509019

Chinese Journal of Organic Chemistry

ARTICLE

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

^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, Hao^a, Quan, Xiaoxin^a, Zhang, shenghai^a, She, Wei^b

^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

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

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Zhang, Jidong, Wang, Hao, Quan, Xiaoxin, Zhang, shenghai, She, Wei. Synthesis of AIE Effect Organic Polymorphs Based on Tetraphenylethene Structure: Research on Molecular Conformation and Detection Performance[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202509019.

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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

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

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