Bicyclic Phenyl–Ethynyl Architectures: Synthesis of a 1,4‐Bis(phenylbuta‐1,3‐diyn‐1‐yl) Benzene Banister,Chemistry - A European Journal

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Bicyclic Phenyl–Ethynyl Architectures: Synthesis of a 1,4‐Bis(phenylbuta‐1,3‐diyn‐1‐yl) Benzene Banister
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2021-01-27 , DOI: 10.1002/chem.202005207
Linda Maria Bannwart ₁ , Thomas Müntener ₂ , Michel Rickhaus ₃ , Lukas Jundt ₁ , Daniel Häussinger ₁ , Marcel Mayor _{1,

4,

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Affiliation

The novel diacetylene bridged terphenylic macrocycle 1 is presented and discussed in the context of rotationally restricted “Geländer” oligomers. The 1,4‐bis(phenylbuta‐1,3‐diyn‐1‐yl) benzene bridge of diacetylene 1 is significantly longer than its terphenyl backbone, forcing the bridge to bend around the central pylon. The synthesis of molecule 1 is based to a large extent on acetylene scaffolding strategies, profiting from orthogonal alkyne protection groups to close both macrocyclic subunits by oxidative acetylene coupling sequentially. The spatial arrangement and the dynamic enantiomerization process of the bicyclic target structure 1 are analyzed. In‐depth NMR investigations not only reveal an unexpected spatial arrangement with both oligomer strands bent alongside the backbone, but also display the limited stability of the model compound in the presence of molecular oxygen.

中文翻译：

双环苯基-乙炔基结构：1,4-双(苯基丁-1,3-二炔-1-基)苯Banister的合成

在旋转限制的“Geländer”低聚物的背景下，介绍并讨论了新型二乙炔桥连三联苯大环1 。丁二炔1的 1,4-双（苯基丁-1,3-二炔-1-基）苯桥明显长于其三联苯主链，迫使桥绕中心塔弯曲。分子1的合成在很大程度上基于乙炔支架策略，利用正交炔保护基团通过氧化乙炔偶联顺序封闭两个大环亚基。分析了双环目标结构1的空间排列和动态对映过程。深入的核磁共振研究不仅揭示了两条低聚物链沿着主链弯曲的意想不到的空间排列，而且还显示了模型化合物在分子氧存在下的有限稳定性。

更新日期：2021-01-27

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