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Synthesis and Nonlinear Optical Properties of Chromophores with 1,8-Dimethoxy-9,10-dihydroanthracene and Ring-locked Triene

Synthesis and Nonlinear Optical Properties of Chromophores with 1,8-Dimethoxy-9,10-dihydroanthracene and Ring-locked Triene
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摘要 The new chromophore molecules with nonlinear optical (NLO) properties were prepared by Knoevenagel condensation from 1,8-dimethoxy-4,5-diformyl-9,10-dihydroanthracene and isophorone derivative in the presence of piperidine and acetic acid. In these chromophore, the ring-locked trienes were employed as the conjugation bridge and electron acceptor in D-π-A units. The key intermediate dialdehyde was conveniently prepared via a three step reaction, in which 1,8-dimethoxyanthraquinone was reduced with zinc/acetic acid and sodium/ethanol successively, followed by formylation with 1,1-dichlorodimethyl ether in the presence of TiCI4. The solvatochromism and UV spectra indicate that they have higher second-order nonlinear hyperpolarizability μβ values than the corresponding reference compound, without red shift of the charge transfer band. The new chromophore molecules with nonlinear optical (NLO) properties were prepared by Knoevenagel condensation from 1,8-dimethoxy-4,5-diformyl-9,10-dihydroanthracene and isophorone derivative in the presence of piperidine and acetic acid. In these chromophore, the ring-locked trienes were employed as the conjugation bridge and electron acceptor in D-π-A units. The key intermediate dialdehyde was conveniently prepared via a three step reaction, in which 1,8-dimethoxyanthraquinone was reduced with zinc/acetic acid and sodium/ethanol successively, followed by formylation with 1,1-dichlorodimethyl ether in the presence of TiCI4. The solvatochromism and UV spectra indicate that they have higher second-order nonlinear hyperpolarizability μβ values than the corresponding reference compound, without red shift of the charge transfer band.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2007年第1期116-120,共5页 中国化学(英文版)
基金 Project supported by the Science Foundation of Jiangsu Province of China (No. BK2004085) and the National Natural Science Foundation of China (No. 90101018).
关键词 NLO CHROMOPHORE nonlinear optics HYPERPOLARIZABILITY SYNTHESIS NLO, chromophore, nonlinear optics, hyperpolarizability, synthesis
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