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Citation: 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 Chimica Sinica, ;2016, 74(11): 885-892. doi: 10.6023/A16080435 shu

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

  • 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

  • Corresponding author: Hu Rongrong, msrrhu@scut.edu.cn Tang Ben Zhong, tangbenz@ust.hk
  • Received Date: 25 August 2016

    Fund Project: National Basic Research Program of China 973 Program; 2013CB834701the Innovation and Technology Commission ITC-CNERC14S01the Guangdong Natural Science Funds 2016A030306045the Fundamental Research Funds for the Central Universities 2015ZY013and the Guangdong Innovative Research Team Program 201101C0105067115the National Natural Science Foundation of China 21404041the National Natural Science Foundation of China 21490573the National Natural Science Foundation of China 21490574the Fundamental Research Funds for the Central Universities 2015ZJ002

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  • 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 φw=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.
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