Construction and Properties of Flexible Light-Emitting Materials Based on Tetraphenylethylene

doi:10.6023/cjoc202403051

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2538-2544.DOI: 10.6023/cjoc202403051 Previous Articles Next Articles

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基于四苯乙烯的柔性发光材料的构筑及性能研究

王源浩^a, 孙钰凯^a, 刘昱迒^a^,^b, 张照明^a^,^*(), 颜徐州^a^,^b^,^*()

a 上海交通大学化学化工学院上海 200240
b 上海交通大学变革性分子前沿科学中心上海 200240

收稿日期:2024-03-30 修回日期:2024-05-23 发布日期:2024-06-13
作者简介:
† 共同第一作者.
基金资助:
聚烯烃催化技术与高性能材料国家重点实验室和上海市聚烯烃催化技术重点实验室(SKL-LCTP-202301); 西安交通大学金属材料强度国家重点实验室(20222409)

Construction and Properties of Flexible Light-Emitting Materials Based on Tetraphenylethylene

Yuanhao Wang^a, Yukai Sun^a, Yuhang Liu^a^,^b, Zhaoming Zhang^a(), Xuzhou Yan^a^,^b()

a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
b Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240

Received:2024-03-30 Revised:2024-05-23 Published:2024-06-13
Contact: *E-mail: zhangzhaoming@sjtu.edu.cn; xzyan@sjtu.edu.cn
About author:
† The authors contributed equally to this work.
Supported by:
State Key Laboratory of Polyolefins and Catalysis and Shanghai Key Laboratory of Catalysis Technology for Polyolefins(SKL-LCTP-202301); State Key Laboratory for Mechanical Behavior of Materials(20222409)

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Abstract

Flexible light-emitting materials find broad applications across various realms of technical production owing to their capacity to uphold structural integrity and luminescent efficacy amidst diverse external forces. In this study, a range of flexible light-emitting materials featuring tunable fluorescence intensity have been synthesized with tetraphenylethylene as the chromophore group, employing a highly efficient thiol-ene click polymerization. By adjusting the ratio of thiol monomers with varying functional degrees involved in polymerization, a polymer network with superior mechanical properties is achieved. This network exhibits an elongation at break of 377%, a fracture stress of 33.0 MPa, and an impressive toughness of up to 90.6 MJ/m³. Because of the changes of molecular conformation owing to the external forces, the fluorescence quantum yield of the materials rises in tandem with the degree of stretching. Additionally, fluorescence quenching is observed following swelling, and the fluorescence re-emerging upon solvent volatilization, aligning with the principles of aggregation-induced emission. Drawing from the aforementioned study, this flexible light-emitting materials exhibit exceptional mechanical characteristics and tunable fluorescence intensity, poised to find practical utility in the realm of light-emitting sensors and signal detection.

Key words: aggregation-induced emission, flexible light-emitting materials, polymer network, mechanical properties, modulated fluorescence intensity

Cite this article

Yuanhao Wang, Yukai Sun, Yuhang Liu, Zhaoming Zhang, Xuzhou Yan. Construction and Properties of Flexible Light-Emitting Materials Based on Tetraphenylethylene[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2538-2544.

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Fig. & Tab. 7

Figure 1. Construction of cross-linked networks and changes in fluorescence intensity in different situations

Figure 2. (a) TGA curves of TPE-0, TPE-1 and TPE-2 under 50 mL/min N2 flow, and (b) DSC curves of TPE-0, TPE-1 and TPE-2 with a heating rate of 20 ℃/min

Figure 3. (a) Stress-strain curves of TPE-0, TPE-1 and TPE-2 with the deformation rate of 100 mm/min; (b) Young’s modulus and toughness of TPE-0, TPE-1 and TPE-2 (the data were derived from stress-strain curves)

Figure 4. Variation of fluorescence quantum efficiency with strain

Figure 5. (a) Sample without subsequent processing, (b) sample after swelling for 3 h, and (c) sample after swelling and vacuum drying placed under 365 nm light

Figure 6. Variation in fluorescence quantum efficiency of the three samples before and after swelling The a, b and c present the three samples in Figure 5.

Scheme 1. Synthesis of compound 4

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基于四苯乙烯的柔性发光材料的构筑及性能研究

Construction and Properties of Flexible Light-Emitting Materials Based on Tetraphenylethylene

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Fig. & Tab. 7

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