Acta Phys. -Chim. Sin. ›› 2014, Vol. 30 ›› Issue (5): 980-986.doi: 10.3866/PKU.WHXB201403031

• PHOTOCHEMISTRY AND RADIATION CHEMISTRY • Previous Articles     Next Articles

Synthesis and Optical Limiting Behaviors of Malononitrile Derivatives

WANG Liu-Heng1,2, PENG Rong-Zong1,2, ZHAO Yu-Xia1, WU Fei-Peng1   

  1. 1 Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China;
    2 University of Chinese Academy of Sciences, Beijing 100049, P. R. China
  • Received:2014-01-22 Revised:2014-02-27 Published:2014-04-25
  • Contact: ZHAO Yu-Xia, WU Fei-Peng;
  • Supported by:

    The project was supported by the Joint Fund of the National Natural Science Foundation of China and the China Academy of Engineering Physics (U1230123).


A series of malononitrile derivatives (D1-D7) with different electron donors and conjugation lengths were designed and synthesized. Their structures were characterized using 1H and 13C nuclear magnetic resonance (NMR) spectroscopies, and high-resolution mass spectrometry (HRMS). Their linear photophysical properties were investigated in dimethylformamide (DMF) solutions, their optical stabilities were investigated using photobleaching experiments, and their thermal stabilities were determined using thermogravimetric analysis (TGA). The optical limiting behaviors of D1-D7 under an 800 nm femtosecond pulsed laser (Ti:sapphire laser, ~130 fs, 1000 Hz) were investigated. The results showed that four of the compounds (D4-D7), which had dialkylamines as electron donors, exhibited significant optical limiting behaviors, based on two-photon absorption (2PA), but the other three compounds (D1-D3), which had either weak donors or short conjugation lengths, showed very weak optical limiting behaviors. All the compounds had good photochemical and thermal stabilities. The 2PA cross-sections and optothermal stabilities of this series of compounds increased with increasing conjugation length or electron-donating ability of the alkylamine groups in their structures. D7, which had the best properties, is a potential candidate for optical limiting applications under an 800 nm femtosecond pulsed laser.

Key words: Optical limiting, 800 nm ultrafast laser, Two-photon absorption, Nonlinear transmission, Malononitrile derivative


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