Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Faculty of Pharmacy, University of Castilla-La Mancha, Calle Almansa 14-Edif. Bioincubadora, 02008, Albacete, Spain.
Chemistry. 2019 Oct 11;25(57):13146-13151. doi: 10.1002/chem.201901837. Epub 2019 Aug 21.
Diphosphahexaarenes are highly stable π-extended frameworks containing two six-membered phosphorus heterocycles that have emerged recently. Herein, we present a detailed investigation on the post-functionalization reactions of their phosphorus centers with special emphasis on the selectivity of the processes and the impact of the phosphorus functionalizations into the physicochemical properties. These studies reveal that indeed the phosphorus atoms of the diphosphahexaarenes are readily available to be functionalized with quaternizing and oxidizing agents as well as borane groups without compromising the stability of the system. In addition, the optoelectronic properties of the diphosphahexaarenes are impacted by the phosphorus post-modifications.
二膦并六元芳环是一类高稳定性的π-扩展骨架,包含两个六元磷杂环。本文详细研究了其磷中心的后续官能团化反应,特别关注了反应的选择性以及磷官能团化对物理化学性质的影响。这些研究表明,二膦并六元芳环的磷原子确实可以与季铵化和氧化试剂以及硼烷基团进行官能团化,而不会影响体系的稳定性。此外,磷的后修饰会影响二膦并六元芳环的光电性质。