Abstract
A novel double aza-oxa[7]helicene was synthesized from the commercially available N1,N4-di(naphthalen-2-yl)benzene-1,4-diamine and p-benzoquinone in two steps. Combining the acid-mediated annulation with the electrochemical sequential reaction (oxidative coupling and dehydrative cyclization) afforded this double hetero[7]helicene. Moreover, the structural and optical features of this molecule have been studied using X-ray crystallographic analysis, and the absorption and emission behaviors were rationalized based on DFT calculations.
Funder
JSPS KAKENHI
Digitalization-driven Transformative Organic Synthesis
Ministry of Education, Culture, Sports, Science, and Technology
Japan Society for the Promotion of Science (JSPS), JST CREST
Hoansha Foundation
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference68 articles.
1. Recent advances in functionalizations of helicene backbone;Jakubec;J. Org. Chem.,2020
2. One hundred years of helicene chemistry. Part 3: Applications and properties of carbohelicenes;Gingras;Chem. Soc. Rev.,2013
3. Helicenes: Synthesis and applications;Shen;Chem. Rev.,2012
4. Crassous, J., Stara, I.G., and Stary, I. (2022). Helicenes: Synthesis, Properties, and Applications, John Wiley & Sons.
5. One hundred years of helicene chemistry. Part 1: Non-stereoselective syntheses of carbohelicenes;Gingras;Chem. Soc. Rev.,2013
Cited by
8 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献