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Nonlinear optical properties of the novel kind of organic donor-acceptor thiophene derivatives with click chemistry modification
Tetrahedron ( IF 2.1 ) Pub Date : 2017-09-21 , DOI: 10.1016/j.tet.2017.09.020
Pengbo Han , Zhou Yang , Hui Cao , Wanli He , Dong Wang , Jingjing Zhang , Yan Xing , Hong Gao

Two new classes of organic third-order optical chromophores, D-π-A-D and D-π-A-D-A-π–D, were designed and synthesized using a Sonogashira coupling reaction and the high-yielding [2 + 2] click reaction. The photophysical and click chemistry were characterized by means of UV/Vis absorption spectroscopy. The electrochemical properties were characterized by means of cyclic voltammetry. Moreover, the third-order nonlinear properties, including the nonlinear refraction and the nonlinear absorption, were investigated by using Z-scan techniques. The chromophores with a D-π-A-D-A-π-D motif, Bt1-X and Bt2-X, exhibited the larger third-order susceptibility χ(3) value than the analogues (D-π-A-D), St1-X and St2-X, whereas the bithiophene chromophores, St2 and Bt2, exhibited a larger χ(3) value than their single thiophene counterparts, St1 and Bt1. Upon the introduction of electron acceptors, third-order nonlinear absorption of the products Stn-X showed a typical SA-RSA transition. Interestingly, the chromophores with a D-π-A-D-A-π-D motif, Btn-X, exhibited more diversified NLO phenomenon. All of the click compounds showed the considerable third-order susceptibility χ(3) values. The results of these studies could provide new molecular-design strategies for third-order nonlinear optical materials for optoelectronic device components.



中文翻译:

单击化学修饰的新型有机供体-受体噻吩衍生物的非线性光学性质

利用Sonogashira偶联反应和高产[2 + 2]点击反应,设计并合成了两类新的有机三阶光学发色团D-π-AD和D-π-ADA-π-D。通过UV / Vis吸收光谱对光物理化学和点击化学进行了表征。电化学性质通过循环伏安法表征。此外,使用Z扫描技术研究了三阶非线性性质,包括非线性折射和非线性吸收。具有D-π-ADA-π-D基序Bt 1 -XBt 2 -X的发色团比类似物(D-π-AD)St表现出更大的三阶磁化率χ (3)1 -XSt 2 -X,而联噻吩发色团St 2Bt 2表现出比其单独的噻吩对应物St 1Bt 1更大的χ(3)值。在引入电子受体后,产物St n -X的三阶非线性吸收显示出典型的SA-RSA跃迁。有趣的是,具有D-π-ADA-π-D基序Bt n -X的发色团表现出更加多样化的NLO现象。所有的点击化合物都显示出相当高的三阶磁化率χ(3)价值观。这些研究的结果可以为光电器件的三阶非线性光学材料提供新的分子设计策略。

更新日期:2017-09-21
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