Binaphthyl-derived armchair-type molecular carbon rings with chirality: synthesis and optical properties†

Qiang Huang , Jinling Zhang , Huafeng Chen , Xin Kong , Peng Xu , Pingwu Du
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Abstract

Herein, we report the synthesis of binaphthyl-derived hoop-shaped aromatic hydrocarbon enantiomers (RCR and SCR) as the segments of (9,9) armchair CNTs. After the structures were identified by HR-MS (MALDI-TOF) and NMR spectroscopy, further circular dichroism (CD) analysis confirmed their chirality. Unlike most of the previously reported chiral-type CNT segments in which chirality arises from the absence of a plane of symmetry or an inversion center in the molecule, the chirality for RCR and SCR is assigned to the introduction of foreign chiral sources, namely, oxyethyl-modified binaphthyl units. Finally, their photophysical properties were also investigated by absorption and fluorescence spectroscopies.

Abstract Image

具有手性的联萘衍生扶手椅型分子碳环:合成和光学性质†
在此,我们报道了联萘衍生的环状芳烃对映体(RCR和SCR)作为(9,9)扶手椅碳纳米管的片段的合成。在通过HR-MS(MALDI-TOF)和NMR光谱鉴定结构后,进一步的圆二色性(CD)分析证实了它们的手性。与大多数先前报道的手性型CNT片段不同,其中手性是由分子中不存在对称平面或反转中心引起的,RCR和SCR的手性归属于引入外来手性源,即羟乙基修饰的联萘单元。最后,用吸收光谱和荧光光谱研究了它们的光物理性质。
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CiteScore
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