Stereoselective synthesis and higher-order derivatization of planar chiral cyclophanes

本文采用Suzuki-Miyaura偶联法合成了C_2对称的对映体纯聚对环己烷衍生物，其中以苯乙烯基亚砜衍生物为基础的氢键控制策略合成了C_2对称的对环己烷衍生物。双striflates是由单体环番的二对苯二酚衍生物衍生而来，被用作它们的低聚物合成的基石。加入苯基间隔剂维持π共轭是成功的，得到了七苯基衍生物。单晶x射线分析证实了其结构，揭示了其线性结构。该化合物的紫外可见光谱和CD光谱表明在有机溶剂（如氯仿）中聚苯骨架呈螺旋构象。

This syntheses of C_2-symmetric enantiomerically pure polyparacyclophane derivatives were achieved by Suzuki-Miyaura coupling method, where the synthesis of these C_2 -symmetrical paracyclophanes was based on the hydrogen-bond controlling strategy by using styryl sulfoxide derivatives. Bistriflates, derived from dihydroquinone derivative of monomeric cyclophanes, were used as building blocks for their oligomer synthesis. Incorporation of phenyl spacer to sustain π-conjugation was successful, giving a heptaphenylene derivative. The structure was confirmed by single crystal X-ray analysis, revealing its linear structure. UV-vis and CD spectra of the compound suggested a helical conformation of thepolyphenylene skeleton in organic solvents, such as chloroform.