Pigulski Bartłomiej, Misiak Klaudia, Męcik Patrycja, Szafert Sławomir
Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383, Wrocław, Poland.
Chemistry. 2023 Dec 11;29(69):e202302725. doi: 10.1002/chem.202302725. Epub 2023 Oct 20.
This study shows the first example of cycloaddition-retro-electrocyclization (CA-RE) click reaction involving nitrogen end-capped push-pull oligoynes. The reported CA-RE reaction with TCNE (tetracyanoethylene) is fully regioselective and leads exclusively to the unprecedented TCBD (tetracyanobuta-1,3-diene-2,3-diyl) end-capped carbon rods. The molecular structure of the products was unambiguously confirmed using X-ray single crystal diffraction and their optical and electronic properties were investigated experimentally and rationalized using DFT (density functional theory) calculations.
本研究展示了涉及氮封端推拉型低聚炔的环加成-逆电环化（CA-RE）点击反应的首个实例。所报道的与四氰基乙烯（TCNE）的CA-RE反应具有完全的区域选择性，并且仅生成前所未有的由四氰基丁-1,3-二烯-2,3-二基封端的碳棒。使用X射线单晶衍射明确证实了产物的分子结构，并通过实验研究了它们的光学和电子性质，同时使用密度泛函理论（DFT）计算进行了合理化分析。
