Deussen, Heinz-Josef; Boutton, Carlo; Thorup, Niels; Geisler, Tommy; Hendrickx, Eric; Bechgaard, Klaus; Persoons, Andre; Bjornholm, Thomas published the artcile< New chiral bis(dipolar) 6,6'-disubstituted binaphthol derivatives for second-order nonlinear optics>, Electric Literature of 112-63-0, the main research area is chiral binaphthol naphthodioxepin derivative nonlinear optic; dioxepin dinaphtho chiral derivative nonlinear optic; crystal structure chiral binaphthol derivative; mol structure chiral binaphthol derivative; dipole moment chiral binaphthol derivative; second harmonic generation chiral binaphthol derivative; hyperpolarizability chiral binaphthol derivative; SHG chiral binaphthol derivative; NLO chiral binaphthol derivative; atropisomer chiral binaphthol derivative NLO.
Several chiral mols. with C2 symmetry derived from two geometries of the binaphthol (BN) system substituted with different acceptors have been synthesized in order to study the possibility of producing noncentrosym. crystals formed from these chiral structures. All the mols. possess two equal donor-acceptor (D – A) systems linked together to give a bis(dipolar) V-shaped system. The dihedral angle θ between the two connected D – A systems has been controlled by chem. methods; this leads to distinct changes in the optical spectra of the connected D – A chromophores, primarily changes caused by effective conjugation of the D – A system imposed by conformation constraints. The crystal structure of chiral (S)-2,2′-diethoxy-1,1′-binaphthyl-6,6′-dicarbaldehyde has been elucidated and indicates that the dipoles in the naphthyl moiety within the overall noncentrosym. crystal can cancel out exactly despite the noncentrosymmetry. The crystal structure of racemic 9,14-dicyanodinaphtho[2,1-d:1′,2′-f][1,3]-dioxepin [(±)-I, A = CN] was found to be centrosym. The new compounds were investigated for second-harmonic generation (including BN derivatives reported earlier) by the Kurtz – Perry powder test to evaluate the second-order nonlinear optical (NLO) properties of polycrystalline samples. Although chirality ensures noncentrosym. crystals, only modest (≈ 2-methyl-4-nitroaniline) or no nonlinearities were observed in the powder test. For a representative selection of the mols., the first mol. hyperpolarizabilities βz were shown to be very high [up to 888 × 10-30 esu for II with A = (E)-CH:CH(p-PhCHC(CN)2)] by elec. field induced second harmonic generation (EFISHG) measurements. Synthetic routes are reported for optically pure 6,6′-disubstituted-2,2′-diethoxy-1,1′-binaphthyls [II; A = CN, SO2CH3, (E)-CH:CHSO2CH3, (E)-CH:CH(p-PhCN), (E)-CH:CH(p-PhSO2CH3), (E)-CH:CH(p-PhCH:C(CN)2), (E)-CH:CHCH:C(CN)2] and optically pure 9,14-disubstituted-dinaphtho[2,1-d:1′,2′-f][1,3]dioxepins [I; A = CN (only racemic), SO2CH3, (E)-CH:CH(p-PhCN), (E)-CH:CH(p-PhSO2CH3), (E)-CH:CH(p-PhNO2), (E)-CH:CH(p-PhCH:C(CN)2), (E)-CH:CHCH:C(CN)2].
Chemistry – A European Journal published new progress about Acetals, cyclic Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Electric Literature of 112-63-0.
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