A series of asymmetric triphenylene derivatives containing typical D–π–A structures is successfully synthesized by means of [2+2] cycloaddition–cycloreversion click reactions. The photophysical and electrochemical properties, as well as the click reactions, are characterized by means of UV/Vis absorption spectroscopy, cyclic voltammetry, and DFT modulations. In addition, the third-order nonlinear properties, including the nonlinear absorption and the nonlinear susceptibilities, are investigated by using Z-scan techniques. A typical reverse saturable absorption–saturable absorption behavior is observed for the third-order nonlinear absorption, with the third-order nonlinear susceptibilities of the compounds being 1.05×10−12, −1.50×10−12, and −0.52×10−12 esu, respectively.
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