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This paper aims to prepare third-order nonlinear optical (NLO) organic materials with large nonlinear optimization value, high damage threshold and ultrafast response time.

A series of novel symmetric and asymmetric compounds possessing third-order NLO properties were synthesized using 1,3,5-tribromobenzene as the basis. The photophysical and electrochemical properties, as well as the click reactions, were characterized by means of UV–VIS–NIR absorption spectroscopy and cyclic voltammetry.

The donor–acceptor chromophores were inserted into compound, making the molecule to have a broader absorption in the near-infrared regions and a narrower optical and electrochemical band gap. It also formed an electron-delocalized organic system, which has larger effects on achieving a third-order NLO response. The third-order NLO phenomenon of benzene ring complexes was experimentally studied at 532 nm using Z-scan technology, and some compounds showed the expected NLO properties.

The click products exhibit more NLO phenomena by performing different click combinations to the side groups, opening new perspectives on using the system in a variety of photoelectric applications.