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Encapsulation of Cofacial Diarylacetylene Dimers Using [
Heterocycles ( IF 0.6 ) Pub Date : 2023-11-29 , DOI: 10.3987/com-23-14921
Susumu Tsuda , Yutaka Nishiyama , Kaito Kawakita , Yumeki Yano , Naoto Yasumura , Shin-ichi Fujiwara

[c2]Daisy chain rotaxanes are mechanically interlocked molecules that can cofacially assemble two π-conjugated molecules. In this study, we employed a rotaxane architecture to encapsulate diarylacetylene dimers modified with an electron-withdrawing or electron-donating substituent in two permethylated α-cyclodextrins. Solvent- and concentration-dependent 1H nuclear magnetic resonance measurements indicated the selective formation of the cofacial dimers. These dimers were mechanically interlocked by condensation with 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-3,5-dimethylaniline to obtain the corresponding [c2]daisy chain rotaxanes (up to 68% yield). UV-visible absorption and fluorescence spectra revealed that the diarylacetylene substituents modulated the optical properties of the rotaxanes.

中文翻译:

使用 [ 封装表面二芳基乙炔二聚体

[ c 2]菊链轮烷是机械互锁的分子,可以共面组装两个π-共轭分子。在这项研究中,我们采用轮烷结构将用吸电子或供电子取代基修饰的二芳基乙炔二聚体封装在两个全甲基化α-环糊精中。溶剂和浓度依赖性1 H 核磁共振测量表明共面二聚体的选择性形成。这些二聚体通过与4-{2-[2-(2-羟基乙氧基)乙氧基]乙氧基}-3,5-二甲基苯胺缩合进行机械联锁,得到相应的[ c 2]菊链轮烷(产率高达68%)。紫外-可见吸收和荧光光谱表明二芳基乙炔取代基调节轮烷的光学性质。
更新日期:2023-11-29
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