Synthesis of Aggregation-Induced Emission (AIE) Organic Polymorphs Based on Tetraphenylethene Structure: Research on Molecular Conformation and Detection Performance of Cys

doi:10.6023/cjoc202509019

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 934-940.DOI: 10.6023/cjoc202509019 Previous Articles Next Articles

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基于四苯乙烯结构的聚集诱导发光效应(AIE)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

修回日期:2025-11-21 发布日期:2025-12-30
基金资助:
陕西省重点研发计划(2023YBGY-152); 陕西省基础科学研究院科学研究计划(23JHQ033); 陕西省教育厅专项科研计划(23JK0274); 及陕西省大学生创新创业训练计划(S202311397067); 及陕西省大学生创新创业训练计划(S202411397065)

Synthesis of Aggregation-Induced Emission (AIE) Organic Polymorphs Based on Tetraphenylethene Structure: Research on Molecular Conformation and Detection Performance of Cys

Jidong Zhang^a^,^*(), Hao Wang^a, Xiaoxin Quan^a, Shenghai Zhang^a, Wei She^b

^a College of Chemistry and Environment, Ankang University, Ankang, Shaanxi 725000
^b Institute of Chemistry, Baotou Teachers College, Baotou, Inner Mongolia 014030

Revised:2025-11-21 Published:2025-12-30
Contact: *E-mail: akuzjd@aku.edu.cn
Supported by:
Shaanxi Provincial Key Research and Development Program(2023YBGY-152); Scientific Research Program of Shaanxi Academy of Basic Sciences(23JHQ033); Special Scientific Research Program of the Shaanxi Provincial Department of Education(23JK0274); Shaanxi Provincial College Students’ Innovation and Entrepreneurship Training Program(S202311397067); Shaanxi Provincial College Students’ Innovation and Entrepreneurship Training Program(S202411397065)

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Abstract

A tetraphenylethene based 2,4-dinitrobenzenesulfonyl derivative TPE-1 with aggregation-induced emission (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 (0.3.1097 nm), and the C—H…π interaction in TPE-1t (0.27640 nm). Due to the influence of torsion angle on the structure, the two crystals form different arrangement patterns at the ends. These results inferred that the molecular conformation significantly affects the luminescence characteristics. Crystals with slightly 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 phosphate buffer solution (PBS), and the detection limit is 26.7 nmol/L.

Key words: polymorph, aggregation-induced emission (AIE), fluorescence probe, cysteine

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Jidong Zhang, Hao Wang, Xiaoxin Quan, Shenghai Zhang, Wei She. Synthesis of Aggregation-Induced Emission (AIE) Organic Polymorphs Based on Tetraphenylethene Structure: Research on Molecular Conformation and Detection Performance of Cys[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 934-940.

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Fig. & Tab. 6

Scheme 1. Synthetic route of compound TPE-1

Figure 1. (a) Fluorescence emission spectra of TPE-1 in THF/H2O with different water fractions (10 µmol•L－1) (excitation wavelength is 395 nm) and (b) fluorescence emission intensity at 556 nm of TPE-1 as a function of water fraction

Figure 2. Crystal structures of (a) TPE-1s and (b) TPE-1t

Figure 3. Molecular packing structures of (a) TPE-1s and (b) TPE-1t

Figure 4. (a) Fluorescence emission spectra of 10 µmol•L－1 TPE-1s in C2H5OH/PBS (V∶V=7∶3, pH=7.4) solution upon addition of different concentrations of Cys (0~5.0 equiv.), and (b) the fluorescence intensity at 583 nm of probe TPE-1s (10 μmol•L－1) upon addition of different concentrations of Cys (0~5.0 equiv.)

Figure 5. (a, c) TPE-1s (b, d)TPE-1s＋Cys的SEM图像 SEM images of (a, c) TPE-1s and (b, d) TPE-1s＋Cys

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基于四苯乙烯结构的聚集诱导发光效应(AIE)有机多晶体合成: 分子构象和Cys检测性能研究

Synthesis of Aggregation-Induced Emission (AIE) Organic Polymorphs Based on Tetraphenylethene Structure: Research on Molecular Conformation and Detection Performance of Cys

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