Reger David, Schöll Kilian, Hampel Frank, Maid Harald, Jux Norbert
Department of Chemistry and Pharmacy &, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-University Erlangen-Nuremberg, Nikolaus-Fiebiger-Strasse 10, 91058, Erlangen, Germany.
Chemistry. 2021 Jan 26;27(6):1984-1989. doi: 10.1002/chem.202004983. Epub 2021 Jan 12.
In this work we present the solution-synthesis of pyridine analogues to hexa-peri-hexabenzocoronene (HBC)-which might be called superpyridines-via a novel precursor design. The key step in our strategy was the pre-formation of the C-C bonds between the 3/3' positions of the pyridine and the adjacent phenyl rings-bonds that are otherwise unreactive and difficult to close under Scholl-conditions. Apart from the synthesis of the parent compound we show that classical pyridine chemistry, namely oxidation, N-alkylation and metal-coordination is applicable to the π-extended analogue. Furthermore, we present basic physical chemical characterizations of the newly synthesized molecules. With this novel synthetic strategy, we hope to unlock the pyridine chemistry of nanographenes.
在这项工作中，我们通过一种新颖的前体设计，展示了吡啶类似物向六并六苯并蔻（HBC）的溶液合成——这种类似物或许可称为超吡啶。我们策略中的关键步骤是在吡啶的3/3' 位置与相邻苯环之间预先形成碳 - 碳键，这些键在其他情况下是无反应活性的，并且在肖尔条件下难以闭合。除了母体化合物的合成，我们还表明经典的吡啶化学，即氧化、N - 烷基化和金属配位，适用于这种π - 扩展类似物。此外，我们展示了新合成分子的基本物理化学表征。通过这种新颖的合成策略，我们希望开启纳米石墨烯的吡啶化学研究。
