Selective Synthesis of Conjugated Chiral Macrocycles: Sidewall Segments of (-)/(+)-(12,4) Carbon Nanotubes with Strong Circularly Polarized Luminescence.,Angewandte Chemie International Edition

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Selective Synthesis of Conjugated Chiral Macrocycles: Sidewall Segments of (-)/(+)-(12,4) Carbon Nanotubes with Strong Circularly Polarized Luminescence.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-12-04 , DOI: 10.1002/anie.201909401
Jinyi Wang ₁ , Guilin Zhuang ₂ , Muqing Chen ₁ , Dapeng Lu ₁ , Zhe Li ₃ , Qiang Huang ₁ , Hongxing Jia ₁ , Shengsheng Cui ₁ , Xiang Shao ₃ , Shangfeng Yang ₁ , Pingwu Du ₁

Affiliation

Carbon nanotubes (CNTs) have unusual physical properties that are valuable for nanotechnology and electronics, but the chemical synthesis of chirality- and diameter-specific CNTs and π-conjugated CNT segments is still a great challenge. Reported here are the selective syntheses, isolations, characterizations, and photophysical properties of two novel chiral conjugated macrocycles ([4]cyclo-2,6-anthracene; [4]CAn2,6 ), as (-)/(+)-(12,4) carbon nanotube segments. These conjugated macrocyclic molecules were obtained using a bottom-up assembly approach and subsequent reductive elimination reaction. The hoop-shaped molecules can be directly viewed by a STM technique. In addition, chiral enantiomers with (-)/(+) helicity of the [4]CAn2,6 were successfully isolated by HPLC. The new tubular CNT segments exhibit large absorption and photoluminescence redshifts compared to the monomer unit. The carbon enantiomers are also observed to show strong circularly polarized luminescence (glum ≈0.1). The results reported here expand the scope of materials design for bottom-up synthesis of chiral macrocycles and enrich existing knowledge of their optoelectronic properties.

中文翻译：

共轭手性大环化合物的选择性合成：具有强圆偏振发光的（-）/（+）-（12,4）碳纳米管的侧壁片段。

碳纳米管（CNT）具有非同寻常的物理特性，对于纳米技术和电子学来说非常有价值，但是手性和直径特定的CNT和π共轭的CNT链段的化学合成仍然是一个巨大的挑战。这里报道的是两个新型手性共轭大环化合物（[4] cyclo-2,6-蒽; [4] CAn2,6）的选择性合成，分离，表征和光物理性质，为（-）/（+）-（ 12,4）碳纳米管片段。这些共轭的大环分子是使用自下而上的组装方法和随后的还原消除反应获得的。环状分子可以通过STM技术直接查看。另外，通过HPLC成功地分离了[4] CAn2,6具有（-）/（+）螺旋度的手性对映体。与单体单元相比，新的管状CNT链段显示出较大的吸收和光致发光红移。还观察到碳对映体显示出强的圆偏振发光（glum≈0.1）。本文报道的结果扩展了手性大环化合物自下而上合成的材料设计范围，并丰富了其光电子性质的现有知识。

更新日期：2019-12-05

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