Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Department of Chemistry, Columbia University, New York, New York 10027, United States.
J Am Chem Soc. 2022 Nov 9;144(44):20214-20220. doi: 10.1021/jacs.2c09288. Epub 2022 Oct 28.
Here we show the access to single-handed helicene nanoribbons by utilizing a [6]helicene building block to induce diastereoselective, photochemical formation of [5]helicene units. Specifically, we have synthesized nanoribbons and with different ratios of [6]helicene "sergeants" to [5]helicene "soldiers", which on average consist of between ∼50 and 60 -annulated benzene rings. These are the longest, optically active helicene backbones that have been prepared to date. The chiroptic properties of and reveal the transfer of stereochemical information from "sergeants" to "soldiers". To gain further insight into the stereo-information relay, we apply the same molecular design to discrete, model oligomers - and confirm that they also preferentially adopt homochiral geometries.
在这里，我们展示了通过利用[6]螺旋芴砌块来诱导非对映选择性、光化学形成[5]螺旋芴单元，从而获得单手螺旋纳米带的方法。具体而言，我们合成了具有不同[6]螺旋芴“士官”与[5]螺旋芴“士兵”比例的纳米带 和 ，它们平均由约 50 到 60 个薁环组成。这些是迄今为止制备的最长的、光学活性的螺旋芴骨架。和 的手性性质揭示了立体化学信息从“士官”到“士兵”的传递。为了更深入地了解立体信息传递，我们将相同的分子设计应用于离散的模型低聚物-和 ，并证实它们也优先采用同手性几何构型。
