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

doi:10.6023/A16080435

Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (11): 885-892.DOI: 10.6023/A16080435 Previous Articles Next Articles

Article

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).

1. Tetraphenylethene-Containing Alkynone Derivatives: Design and Synthesis, Aggregation-Induced Emission Characteristics, and the Selective Fluorescence Detection of Pd²⁺.PDF(766KB)

Abstract

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

Cite this article

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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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