基于四苯乙烯的柔性发光材料的构筑及性能研究

doi:10.6023/cjoc202403051

有机化学 ›› 2024, Vol. 44 ›› Issue (8): 2538-2544.DOI: 10.6023/cjoc202403051 上一篇下一篇

研究论文

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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摘要/Abstract

柔性发光材料凭借在不同外力作用下仍能保持形状完整和发光性能的特点, 在技术生产的多个领域有着广泛的应用. 利用四苯基乙烯作为发色基团, 利用硫醇与双键高效点击聚合的方法, 构筑了一系列荧光强度可调的柔性发光材料. 通过调节参与聚合的不同官能度硫醇单体的比例, 制备了机械性能优异的聚合物网络, 其断裂伸长率为377%, 断裂应力为33.0 MPa, 韧性可达90.6 MJ/m³. 通过外力诱导分子构象变化, 发现材料的荧光量子产率会随着拉伸程度的增加而升高. 同时, 该材料在溶胀后会发生荧光淬灭, 挥发溶剂后荧光重新出现, 符合聚集诱导发光的规律. 基于以上研究, 该柔性发光材料的机械性能优秀且荧光强度可调, 因此有望在发光传感器、信号探测器等方向开展实际应用.

关键词: 聚集诱导发光, 柔性发光材料, 聚合物网络, 机械性能, 荧光强度调控

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

引用此文

王源浩, 孙钰凯, 刘昱迒, 张照明, 颜徐州. 基于四苯乙烯的柔性发光材料的构筑及性能研究[J]. 有机化学, 2024, 44(8): 2538-2544.

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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图/表 7

图1. 交联网络的构筑及其在不同情况下荧光变化情况

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

图2. (a) 50 mL/min N2流量下TPE-0、TPE-1与TPE-2的TGA曲线, 以及(b) TPE-0、TPE-1与TPE-2的DSC曲线(升温速率为20 ℃/min)

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

图3. (a) 拉伸速率100 mm/min 下TPE-0、TPE-1与TPE-2的应力-应变曲线, 以及(b) TPE-0、TPE-1与TPE-2的杨氏模量与韧性对比(数据计算来源于应力-应变曲线)

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)

图4. 荧光量子产率随伸长率变化情况

Figure 4. Variation of fluorescence quantum efficiency with strain

图5. (a)无后续处理的样品、(b)溶胀3 h后的样品和(c)溶胀并真空干燥后的样品放置在365 nm光照下的情景

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

图6. 溶胀前后三种样品荧光量子产率变化情况

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.

图式1. 化合物4的合成

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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