Synthesis, third-order nonlinear optical properties and theoretical analysis of vinylferrocene derivatives

Abstract

A series of vinylferrocene derivatives were synthesized from the reaction of ferrocenecarboxaldehyde, alcohol, and triphenylphosphonium bromide in a one-pot, solid-state reaction. Their third-order nonlinear optical (NLO) properties were evaluated in N,N-dimethylformamide at 800 nm using femtosecond degenerate four-wave mixing. The third-order NLO susceptibilities of the compounds were 2.55–3.78 × 10 −13 esu. The second-order hyperpolarizabilities of the molecules were 2.42–3.60 × 10 −31 esu. The response times were 51–98 fs. The energy of the Highest Occupied Molecular Orbital (HOMO), the Lowest Unoccupied Molecular Orbital (LUMO), the energy gap of the HOMO and LUMO ( E gap ), natural charge, and molecular orbitals are performed by the Density Function Theory (DFT). The DFT study showed that the third-order NLO properties were increased with the increasing electron-withdrawing ability in accordance with the decreasing E gap and the increasing charge transfer among the donor, π-bridge, and the acceptor. The experiment and theoretical results show that the vinylferrocene derivatives have potential nonlinear optical applications. • A series of vinylferrocene derivatives were synthesized. • The third-order nonlinear optical properties were measured using femtosecond degenerate four-wave mixing. • The energy of HOMO, LUMO, E gap , natural charge, and MOs are performed by DFT.