π‐Extended Diaza[7]helicenes by Hybridization of Naphthalene Diimides and Hexa‐peri‐hexabenzocoronenes,Chemistry - A European Journal

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π‐Extended Diaza[7]helicenes by Hybridization of Naphthalene Diimides and Hexa‐peri‐hexabenzocoronenes
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-08-20 , DOI: 10.1002/chem.202003402
Carolin Dusold ₁ , Dmitry I Sharapa ₂ , Frank Hampel ₁ , Andreas Hirsch ₁

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The synthesis of an unprecedented, π‐extended hexabenzocorene (HBC)‐based diaza[7]helicene is presented. The target compound was synthesized by an ortho‐fusion of two naphthalene diimide (NDI) units to a HBC‐skeleton. A combination of Diels–Alder and Scholl‐type oxidation reactions involving a symmetric di‐NDI‐tolane precursor were crucial for the very selective formation of the helical superstructure via a hexaphenyl‐benzene (HPB) derivative. The formation of the diaza[7]helicene moiety in the final Scholl oxidation is favoured, affording the symmetric π‐extended helicene as the major product as a pair of enantiomers. The separation of the enantiomers was successfully accomplished by HPLC involving a chiral stationary phase. The absolute configuration of the enantiomers was assigned by comparison of circular dichroism spectra with quantum mechanical calculations.

中文翻译：

萘二酰亚胺和六邻六苯并酮杂交制备π-扩展二氮杂[7]螺旋烯

提出了一种前所未有的、基于 π 延伸的六苯并并烯 (HBC) 的二氮杂[7]螺旋烯的合成。目标化合物是通过两个萘二酰亚胺 (NDI) 单元邻位融合到 HBC 骨架上合成的。涉及对称二-NDI-甲苯烷前体的狄尔斯-阿尔德和肖尔型氧化反应的组合对于通过六苯基苯（HPB）衍生物选择性地形成螺旋超结构至关重要。在最终的 Scholl 氧化中，有利于二氮杂[7]螺旋烯部分的形成，从而提供对称的 π 延伸螺旋烯作为一对对映体的主要产物。通过使用手性固定相的 HPLC，成功实现了对映体的分离。通过圆二色光谱与量子力学计算的比较来确定对映体的绝对构型。

更新日期：2020-08-20

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