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Structural and second order nonlinear optical characteristics of four ortho-bridged dibenzaldehydes with alkyloxy- and xylenyloxy linkers are compared from the XRD, UV-Vis-NIR spectroscopic, SHG, and DFT studies. Interruption of electron polarization by π-conjugation of the linkers between the two benzaldehyde units affect their NLO properties like hyperpolarizability (β) in these acceptor–π–bridge–donor–π–bridge–acceptor (A–π–D–π–A) systems. The noncentrosymmetric 2,2′-[1,2-phenylenebis(methylenoxy)]dibenzaldehyde exhibits SHG efficiency matching with that of potassium dihydrogenphosphate (KDP) in Kurtz-Perry powder method. The acentric supramolecular architecture stabilized by H-bonding and aromatic π-π stacking interactions in the solid state with the non-linear o-xylenyloxy linker rationalizes the origin of its structure driven NLO property. Chromophore density, broad optical transparency, low cut-off wavelength of electronic absorptions, and thermal stability of 2,2′-[1,2-phenylenebis(methylenoxy)]dibenzaldehyde make it a promising candidate for second order NLO applications. |
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