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Synthesis and Characterization of Triphenylethylene Derivatives with Aggregation-Induced Emission Characteristics

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Abstract

New aggregation-induced emission (AIE) compounds derived from triphenylethylene were synthesized. The thermal, photophysical, electrochemical and aggregation-induced emissive properties were investigated. All the compounds had strong blue light emission capability and good thermal stability. Their maximum fluorescence emission wavelengths were between 443 to 461 nm in solid states, while their glass transition temperatures ranged from 86 to 129 °C. The decomposition temperatures of the synthesized compounds were in the range of 432–534 °C. The synthesized compounds possessed aggregation-induced emission properties, namely exhibited enhanced fluorescence emission in aggregated states. The highest occupied molecular orbital (HOMO) energy levels estimated from the oxidation potentials were between 5.61 and 5.66 eV and the lowest unoccupied molecular orbital/highest occupied molecular orbital (LUMO/HOMO) energy gap values were found to be in the range of 3.18–3.22 eV. The compounds 4-(4-(2,2-bis(4-(naphthalen-1-yl)phenyl)vinyl)phenyl) dibenzothiophene [(BN)2Bt] and 4-(4-(2,2-di(biphenyl-4-yl)vinyl)phenyl) dibenzothiophene [(BB)2Bt] exhibited vibronic fine-structure photoluminescence spectra when the water fraction was less than 70%.

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Acknowledgments

The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (Grant numbers: 50773096 and 51073177), the Start-up Fund for Recruiting Professionals from “985 Project” of SYSU, the Science and Technology Planning Project of Guangdong Province, China (Grant numbers: 2007A010500001-2, 2008B090500196), Construction Project for University-Industry cooperation platform for Flat Panel Display from the Commission of Economy and Informatization of Guangdong Province (Grant numbers: 20081203), the Fundamental Research Funds for the Central Universities, the Opening Fund of Laboratory Sun Yat-sen University (KF201026), and the Fund for Innovative Chemical Experiment and Research of School of Chemistry and Chemical Engineering.

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Authors and Affiliations

  1. PCFM Lab, DSAPM Lab, KLGHEI of Environment and Energy Chemistry, FCM Institute, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, 510275, China

    Xiao-Fang Li, Zhen-Guo Chi, Bing-Jia Xu, Hai-Yin Li, Xi-Qi Zhang, Wei Zhou, Yi Zhang, Si-Wei Liu & Jia-Rui Xu

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  1. Xiao-Fang Li
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  2. Zhen-Guo Chi
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  9. Jia-Rui Xu
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Correspondence to Zhen-Guo Chi or Jia-Rui Xu.

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Li, XF., Chi, ZG., Xu, BJ. et al. Synthesis and Characterization of Triphenylethylene Derivatives with Aggregation-Induced Emission Characteristics. J Fluoresc 21, 1969–1977 (2011). https://doi.org/10.1007/s10895-011-0896-1

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