Synthesis, crystal structure, electrochemistry and third-order nonlinear optical properties of two novel ferrocene derivatives

•Two novel ferrocene derivatives have been designed, synthesized and fully characterized.•The electrochemical properties of the two compounds were studied by cyclic voltammetric experiments.•The third-order nonlinear optical properties were investigated by Z-scan technique.

Two novel ferrocene derivatives, N,N-diphenyl-4-E-((1-ferrocenyl) ethenyl) aniline (1), N,N-(4,4-diethoxyphenyl)-4-E-((1-ferrocenyl)ethenyl)aniline (2), were designed, synthesized and fully characterized by 1H NMR, 13C NMR, FT-IR and MALDI-TOF-MS spectra. Structure of (1) was confirmed by X-ray diffraction analysis. The UV–visible absorption spectra of the two compounds were investigated and verified by density functional theory (DFT) calculations. Electrochemical and third-order nonlinear optical (NLO) properties have been shown by cyclic voltammetric experiments and open/closed aperture Z-scan measurements. The results show that the two compounds both are highly π-electron delocalization system, indicating potential applications as NLO materials. It is noteworthy that (1) possesses larger two-photon absorption (2 PA) coefficient β, 2 PA cross section σ and the third-order nonlinear susceptibility (χ(3)) than (2).

Graphical abstractTwo novel D1-π-D2 ferrocenyl compounds, (1) and (2), were designed, synthesized and fully characterized. They have potential applications as NLO materials and all-optical switching.Figure optionsDownload full-size imageDownload as PowerPoint slide