含多甲氧基芳香基双查尔酮的合成、表征及光热性能

doi:10.19894/j.issn.1000-0518.210048

摘要/Abstract

摘要：

通过克莱森-施密特（Claisen-Schmidt）反应合成了一种新型双查尔酮衍生物1，4-二［3-（3，4，5-三甲氧基苯基）-2-丙烯酰基］苯（BTAB）。该化合物的结构通过核磁共振波谱仪（NMR）和质谱等技术手段得到确认。采用热综合分析方法测定了DSC／TG曲线，发现该化合物的熔点为230.6℃，热稳定性良好。测定了该化合物的紫外光谱和荧光光谱，λ_max／UV＝357.5 nm，λ_max／EM＝541 nm，表现出较大的紫外吸收波长和荧光发射波长。采用密度泛函理论方法计算获得了BTAB分子的最高占据轨道与最低空轨道能量和极化率，从前线分子轨道组成图发现存在分子内电荷转移现象。用单光束Z-扫描技术获得了BTAB的非线性光学特性，其三阶非线性吸收系数β＝3.15×10^－14m／W，五阶非线性吸收系数γ＝2.7×10^－28m³／W²，属于双光子吸收诱导激发态吸收。BTAB作为一种有用的非线性光学（NLO）候选材料具有潜在应用前景。

关键词: 双查尔酮衍生物, 理论计算, 光热性质

Abstract:

A novel dichalcone derivative, 1, 4-bis [3- (3, 4, 5-trimethoxyphenyl) -2-acryloyl] benzene (BTAB), was synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography-mass spectrometer (LC-MS). The thermogravimetry (TG) /differential scanning thermogravimetry (DSC) analysis shows that the melting point of the compound is 230.6℃ and the thermal stability is good. The maximal wavelengths of ultravioletabsorption and fluorescence emissions are determined as λ_max/UV=357.5 nm, λ_max/EM=541 nm, respectively. The energies of the highest occupied and lowest orbital of molecules and polarizability of BTAB were obtained using the density functional theory method. The phenomenon of intramolecular charge transfer was also found from the molecular orbitals. The optical nonlinearities of the BTAB was confirmed by the single beam Z-scan technique. The third-order nonlinear absorption coefficient β and the fifth order nonlinear absorption coefficient γ are 3.15×10^-14m/W and 2.7×10^-28m³/W², respectively, which belongs to double photon absorption. All these results demonstrate that the chalcone ketones BTAB is promising for non-linear optical applications.

Key words: Dichalcone derivative, Theoretical calculation, Photothermal properties

中图分类号:

O625.4

石玉芳, 王迎进, 孙金鱼, 赵明根. 含多甲氧基芳香基双查尔酮的合成、表征及光热性能[J]. 应用化学, 2022, 39(02): 235-240.

Yu-Fang SHI, Ying-Jin WANG, Jin-Yu SUN, Ming-Gen ZHAO. Synthesis, Characterization, Photothermal Properties of Dichalcone Containing Polymethoxy Aromatic Group[J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 235-240.

图/表 6

图示1　BTAB的合成路线

Scheme 1　Synthetic route of BTAB

图1 BTAB的DSC／TG曲线

Fig.1 DSC／TG curves of BTAB

图2 BTAB的紫外-可见吸收光谱

Fig.2 UV-Vis absorption spectrum of BTAB

图3 BTAB的荧光发射光谱

Fig.3 Fluorescence emission spectrum of BTAB

图4 BTAB的几何结构和分子轨道

Fig.4 Geometry and molecular orbitals of BTAB

图5 BTAB的开孔Z-扫描曲线

Fig.5 Open-aperture Z-scan curve of BTAB

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