含四苯基乙烯的炔酮衍生物的设计合成、聚集诱导发光性质及其对Pd2+的选择性荧光检测

doi:10.6023/A16080435

化学学报 ›› 2016, Vol. 74 ›› Issue (11): 885-892.DOI: 10.6023/A16080435 上一篇下一篇

研究论文

含四苯基乙烯的炔酮衍生物的设计合成、聚集诱导发光性质及其对Pd²⁺的选择性荧光检测

黄玉章^a, 雷洛奇^a, 郑超^a, 危博^a, 赵祖金^a, 秦安军^a, 胡蓉蓉^a, 唐本忠^a,b

a 华南理工大学发光材料与器件国家重点实验室广州 510641;
b 香港科技大学化学系国家人体组织功能重建工程技术研究中心香港分中心香港九龙清水湾

投稿日期:2016-08-25 发布日期:2016-11-24
通讯作者: 胡蓉蓉, 唐本忠 E-mail:msrrhu@scut.edu.cn;tangbenz@ust.hk
基金资助:
项目受科技部973项目（2013CB834701），国家自然科学基金项目（21404041，21490573和21490574），广东省自然科学基金项目（2016A030306045），香港创新科技署（ITC-CNERC14S01），中央高校基本科研业务费（2015ZJ002和2015ZY013），广东省创新团队（201101C0105067115）资助.

Tetraphenylethene-Containing Alkynone Derivatives: Design and Synthesis, Aggregation-Induced Emission Characteristics, and the Selective Fluorescence Detection of Pd²⁺

Huang Yuzhang^a, Lei Luoqi^a, Zheng Chao^a, Wei Bo^a, Zhao Zujin^a, Qin Anjun^a, Hu Rongrong^a, Tang Ben Zhong^a,b

a State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China;
b Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China

Received:2016-08-25 Published:2016-11-24
Supported by:
Project supported by the National Basic Research Program of China (973 Program; 2013CB834701), the National Natural Science Foundation of China (21404041, 21490573 and 21490574), the Guangdong Natural Science Funds (2016A030306045), the Innovation and Technology Commission (ITC-CNERC14S01), the Fundamental Research Funds for the Central Universities (2015ZJ002 and 2015ZY013), and the Guangdong Innovative Research Team Program (201101C0105067115).

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1. 含四苯基乙烯的炔酮衍生物的设计合成、聚集诱导发光性质及其对Pd²⁺的选择性荧光检测.PDF(766KB)

摘要/Abstract

聚集诱导发光（AIE）材料吸引了许多光电器件和生物荧光技术领域的科学家的关注.对聚集诱导发光化合物构效关系的深入理解对于设计新材料至关重要.在本工作中，基于经典的AIE基元四苯基乙烯，设计并合成了一系列具有AIE性质，含不同电子给体/受体取代基的炔酮衍生物.对这一系列化合物的光物理性质进行了系统研究并分别探讨了取代基团对发光波长、发光效率和AIE性质的影响.它们的聚集态最大发射波长位于511～565 nm，在四氢呋喃/水混合溶液中的荧光量子产率可达31%.在末端苯环上的电子给体/受体取代基团会降低聚集态的发光效率，而引入硝基取代基则会在发射波长红移的同时，显著猝灭荧光.最为重要的是，这些化合物结构中的炔酮基元可以在一系列金属离子中选择性地与Pd²⁺配位，猝灭纳米聚集体的发光，并有望作为一个有效的Pd²⁺荧光传感器.

关键词: 聚集诱导发光, 四苯基乙烯, 炔酮, 构效关系, 二价钯离子检测

Organic luminescent materials with aggregation-induced emission (AIE) characteristics have attracted much attention among the scientists in the fields of optoelectronic devices and fluorescence biotechnology. AIE materials overcomes the aggregation-caused quenching problem of traditional organic fluorescent compounds, which possess high fluorescence quantum efficiency in the aggregated states. Thanks to the great research effort of worldwide scientists, a large variety of AIE materials have been developed and the underlying mechanism has been rapidly explored. The deep understanding of the structure-property relationship of AIE compounds is still in an urgent demand for the design of new materials. In this work, based on the classical propeller-shaped AIEgen, tetraphenylethene (TPE), we designed and synthesized a series of electron donor/acceptor-containing alkynone derivatives with AIE feature such as cyano, nitro, butyl and butoxyl groups-substituted alkynone derivatives. Their chemical structures have been fully characterized by ¹H NMR, ¹3C NMR, IR, and HRMS spectra, providing satisfactory analysis results. Their photophysical properties are systematically studied and the effect of substitution groups on the emission maximum, emission efficiency, as well as AIE property are discussed, respectively. Their emission maxima are located at 511~565 nm with the fluorescence quantum yields of up to 31% in the aggregated states in THF/water mixtures with high water content. The fluorescence intensity of the unsubstituted TPE-containing alkynone derivative in THF/H₂O with φ_w=90% water content is 157 times higher than that in THF solution. It is suggested that both electron-donating and electron-withdrawing substitution groups on the terminal phenyl ring decrease the emission efficiency of the aggregated state and the introduction of nitro group dramatically quenches the emission while redshifts the emission maximum. Most importantly, the alkynone groups in these compounds can selectively coordinate with Pd²⁺ among a large variety of metal ions, which quench the emission of the nanoaggregates and possess high sensitivity towards Pd²⁺, demon-strating the potential application as an efficient Pd²⁺ fluorescent sensor.

Key words: aggregation-induced emission, tetraphenylethene, alkynone, structure-property relationship, palladium(II) detection

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黄玉章, 雷洛奇, 郑超, 危博, 赵祖金, 秦安军, 胡蓉蓉, 唐本忠. 含四苯基乙烯的炔酮衍生物的设计合成、聚集诱导发光性质及其对Pd²⁺的选择性荧光检测[J]. 化学学报, 2016, 74(11): 885-892.

Huang Yuzhang, Lei Luoqi, Zheng Chao, Wei Bo, Zhao Zujin, Qin Anjun, Hu Rongrong, Tang Ben Zhong. Tetraphenylethene-Containing Alkynone Derivatives: Design and Synthesis, Aggregation-Induced Emission Characteristics, and the Selective Fluorescence Detection of Pd²⁺[J]. Acta Chim. Sinica, 2016, 74(11): 885-892.

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含四苯基乙烯的炔酮衍生物的设计合成、聚集诱导发光性质及其对Pd²⁺的选择性荧光检测

Tetraphenylethene-Containing Alkynone Derivatives: Design and Synthesis, Aggregation-Induced Emission Characteristics, and the Selective Fluorescence Detection of Pd²⁺

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