Synthesis and nonlinear optical properties of novel chalcone analogues of ferrocenyl biaryl derivatives

• A series of novel chalcone analogues of ferrocenyl biaryl derivatives were synthesized.
• The NLO properties of the complexes were measured.
• The charge-transfer interaction of one of the complexes, was probed by DFT studies.

A series of structurally novel organometallic compounds (3a–g) based on 1-biaryl-3-ferrocenylprop-2-en-1-one, were synthesized by the Suzuki-Miyaura cross-coupling reaction for applications as nonlinear optical (NLO) and liquid crystal (LC) materials. Notably, a single crystal of this class of compounds was obtained for the very first time, and it was found that the two phenyl rings of the chalconyl group were nearly coplanar to one of the cyclopentadienyl rings of ferrocene. Due to the high degree of conjugation, all the chalcone analogues of ferrocenyl biaryl derivatives displayed strong second harmonic generation (SHG) response (0.45–0.60 × 10−30 esu, 3–4 times greater that of potassium dideuterophosphate (KDP)). The density functional theory (DFT) was employed to calculate the main molecular orbital energies and compositions of 3d, based on its crystallographic structure. Compound 3d was found to exhibit excellent NLO properties due to its low Egap and superior charge transfer ability within the conjugated system. This work presents a new approach for the preparation of this class of ferrocenyl biaryl derivatives, which may have potential applications as NLO materials.

A serial of novel 1-biaryl-3-ferrocenylprop-2-en-1-one derivatives were synthesized for nonlinear optica materials. Their second harmonic generation (SHG) response was estimated to be 0.45–0.60 × 10−30 esu. Density functional theory (DFT) is employed to perform the molecular orbital energies and compositions of 3c, one of the title compounds.Figure optionsDownload as PowerPoint slide