C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
J Org Chem. 2018 Feb 2;83(3):1216-1222. doi: 10.1021/acs.joc.7b02694. Epub 2018 Jan 19.
A synthetic pathway to a molecule bearing two molecular nanohoops, including a tetrahydro[6]cycloparaphenylene (4H[6]CPP) fused through two 1,4-dimethoxybenzene units to a 4H[10]CPP, was developed. Similarly, a molecule containing a 4H[6]CPP fused through two 1,4-dimethoxybenzene units to a molecular nanohoop bearing a [6]CPP inserted with two 2,2'-bithiophene-5,5'-diyl groups was synthesized. The Diels-Alder reactions of two (E,E)-1,4-diaryl-1,3-butadienes with 1,4-benzoquinone and the Ni-mediated homocoupling reactions are the key steps for the construction of macrocyclic ring structures. Oxidative aromatization with DDQ converted a hydrogenated system to a fully aromatized nanohoop with 10 aromatic units, including a [6]CPP inserted with two 2,2'-bithiophene-5,5'-diyl groups. The UV-vis and fluorescence spectra of the fused two-hoop systems were investigated.
开发了一种合成包含两个分子纳米环的分子的途径，其中一个四氢[6]并苯（4H[6]CPP）通过两个 1,4-二甲氧基苯单元与一个 4H[10]CPP 融合，同样，合成了一个分子，其中一个 4H[6]CPP 通过两个 1,4-二甲氧基苯单元与一个分子纳米环融合，该纳米环带有两个插入的[6]CPP ，每个 CPP 插入两个 2,2'-联噻吩-5,5'-二基。两个（E，E）-1,4-二芳基-1,3-丁二烯与 1,4-苯醌的 Diels-Alder 反应和 Ni 介导的同偶联反应是构建大环环结构的关键步骤。用 DDQ 进行氧化芳构化将氢化体系转化为完全芳构化的纳米环，其中包含 10 个芳基单元，包括插入两个 2,2'-联噻吩-5,5'-二基的[6]CPP。研究了融合双环系统的 UV-vis 和荧光光谱。
