Two-Dimensional Chirality Transfer via On-Surface Reaction,Journal of the American Chemical Society

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Two-Dimensional Chirality Transfer via On-Surface Reaction
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-09-02 , DOI: 10.1021/jacs.6b05597
Haiming Zhang ₁ , Zhongmiao Gong ₁ , Kewei Sun ₁ , Ruomeng Duan ₂ , Penghui Ji ₁ , Ling Li ₁ , Chen Li ₂ , Klaus Müllen _{2,

3} , Lifeng Chi ₁

Affiliation

Two-dimensional chirality transfer from self-assembled (SA) molecules to covalently bonded products was achieved via on-surface synthesis on Au(111) substrates by choosing 1,4-dibromo-2,5-didodecylbenzene (12DB) and 1,4-dibromo-2,5-ditridecylbenzene (13DB) as designed precursors. Scanning tunneling microscopy investigations reveal that their aryl-aryl coupling reaction occurs by connecting the nearest neighboring precursors and thus preserving the SA lamellar structure. The SA structures of 12(13)DB precursors determine the final structures of produced oligo-p-phenylenes (OPP) on the surface. Pure homochiral domains (12DB) give rise to homochiral domains of OPP, whereas lamellae containing mixed chiral geometry of the precursor (13DB) results in the formation of racemic lamellae of OPP.

中文翻译：

通过表面反应的二维手性转移

通过选择 1,4-二溴-2,5-二十二烷基苯 (12DB) 和 1,4，在 Au(111) 基底上通过表面合成实现了从自组装 (SA) 分子到共价键产物的二维手性转移-dibromo-2,5-ditridecylbenzo (13DB) 作为设计的前体。扫描隧道显微镜研究表明，它们的芳基-芳基偶联反应是通过连接最近的相邻前体而发生的，从而保留了 SA 层状结构。12(13)DB 前体的 SA 结构决定了表面上产生的低聚对亚苯基 (OPP) 的最终结构。纯同手性结构域 (12DB) 产生 OPP 的同手性结构域，而包含前体 (13DB) 混合手性几何结构的薄片导致 OPP 的外消旋薄片的形成。

更新日期：2016-09-02

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