摘要
合成4种查尔酮衍生物:1-(2,3-二氟苯基)-3-(3-氯噻吩-2-基)-2-丙烯-1-酮(0208#)、1-(2,4-二氟苯基)-3-(5-苯基噻吩-2-基)-2-丙烯-1-酮(0809#)、1-(2,3-二氟苯基)-3-(5-苯基噻吩-2-基)-2-丙烯-1-酮(0808#)和1-(2,6-二氟苯基)-3-(5-苯基噻吩-2-基)-2-丙烯-1-酮(0812#).通过核磁共振氢谱(1H NMR)和碳谱(13C NMR)、液相色谱-质谱联用质谱(LC-MS)、紫外-可见吸收光谱(UV-Vis)、荧光发射(EM)光谱和Z-扫描技术对化合物的结构和性质进行了表征.采用密度泛函理论方法计算获得了该4种化合物的最高占据分子轨道与最低空分子轨道能量和极化率,从轨道电子云图发现存在显著的分子内电荷转移现象.大π共轭和电荷转移的结构效应使这4种芳香基查尔酮衍生物表现出良好的三阶非线性光学性质.它们可作为非线性吸收(NLA)和激光防护候选材料,具有潜在应用前景.
Abstract
Four novel chalcone derivatives were synthesized:1-(2,3-difluorophenyl)-3-(3-chloro thiophene-2-yl)-2-propene-1-ketone(0208#),1-(2,4-difluorophenyl)-3-(5-phenylthiophene-2-yl)-2-propene-1-ketone(0809#),1-(2,3-difluorophenyl)-3-(5-phenylthiophene-2-yl)-2-propene-1-ketone(0808#),1-(2,6-difluorophenyl)-3-(5-phenylthiophene-2-yl)-2-propene-1-ketone(0812#).The structures and properties of the compounds were characterized by 1 H NMR,13 C NMR,liquid chromatography-mass spectrometry,ultraviolet-visible spectrum(UV-Vis)absorption spectrum,fluorescence emission(EM)spectrum and Z-scanning technique.The energy and polarizability of the highest occupied molecular orbitals(HOMO)and the lowest unoccupied molecular orbital(LUMO)of the four compounds were obtained by density functional theory,and significant intramolecular charge transfer was found from orbital electron cloud images.The combination of large π-conjugation and charge transfer makes the four aryl chalcone derivatives exhibit good nonlinear optical properties.They can be used as useful candidates for nonlinear absorption(NLA)and have potential applications.
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