Circularly Polarized Luminescence and SHG Chiral Signals of Helical TPE Macrocycles,Chinese Journal of Chemistry

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Circularly Polarized Luminescence and SHG Chiral Signals of Helical TPE Macrocycles
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-09-12 , DOI: 10.1002/cjoc.202100553
Ying‐Xue Yuan _{1,

2} , Ming Hu ₁ , Man Xue ₃ , Ting‐Ting Zhou ₁ , Zhen Zhang ₃ , Yan‐Song Zheng ₁

Affiliation

One pair of new enantiomers of helical tetraphenylethylene (TPE) tetracycle tetradodecylurea, which show aggregation-induced emission (AIE) enhancement effect, were synthesized by attaching four dodecyl chains to a helical TPE tetracycle tetramine through urea linkage. These two TPE helicates bearing long alkyl chains could display strong circular dichroism (CD) and circularly polarized luminescence (CPL) signals not only in solution but also in solid state. Due to strong van der Waals interactions between the alkyl chains, the absolute dissymmetrical factor |g_lum| was up to 6.6 × 10^-3 , which was 2—3 fold larger than that of the helical TPE tetracycle tetramine (TPETA) without long alkyl chains in solution. Due to bearing hydrophilic urea units and hydrophobic long dodecyl chains, the helical TPE tetracycle could form chiral Langmuir-Blodgett (LB) monolayers at air/water interface and showed a strong and stable second harmonic generation (SHG) chiral signals. The degree of chiral excess (DCE) for P-isomer monolayer was up to -0.682 ± 0.0014. This is the first example to detect chirality at the air/water interface for chiral AIE molecules. It provides a new access to the application of chiral AIE compounds in nonlinear optical activity.

中文翻译：

螺旋 TPE 大环化合物的圆偏振发光和 SHG 手性信号

一对新的螺旋四苯基乙烯 (TPE) 四环十四烷基脲对映异构体通过尿素键将四个十二烷基链连接到螺旋 TPE 四环四胺上，合成了具有聚集诱导发射 (AIE) 增强效果的对映异构体。这两种带有长烷基链的 TPE 螺旋不仅在溶液中而且在固态中都可以显示出强烈的圆二色性 (CD) 和圆偏振发光 (CPL) 信号。由于烷基链之间的强范德华相互作用，绝对不对称因子| 摹_LUM | 高达 6.6 × 10 ^-3，这是溶液中没有长烷基链的螺旋形 TPE 四环四胺 (TPETA) 的 2-3 倍。由于带有亲水性尿素单元和疏水性长十二烷基链，螺旋形 TPE 四环可以在空气/水界面形成手性 Langmuir-Blodgett (LB) 单分子层，并显示出强而稳定的二次谐波产生 (SHG) 手性信号。P-异构体单层的手性过剩度 (DCE) 高达 -0.682 ± 0.0014。这是在空气/水界面处检测手性 AIE 分子手性的第一个示例。它为手性 AIE 化合物在非线性光学活性中的应用提供了新的途径。

更新日期：2021-11-15

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