We report the synthesis of catenanes (Hopf links) in water utilizing disulfides and aromatic donor–acceptor interactions. The electron-rich dialkoxynaphthalene (DN) building blocks interact with electron-deficient naphthalenediimide (NDI) moieties connected by a polyamine chain. We study the effect of the polyamine linkers on the behavior of the library. The polyamine’s length and the number of nitrogen atoms in the chain affect the library distribution, leading in some cases to the assembly of catenanes in up to 93% yield.
Eilbigi Dehkordi, M., Luxami, V., & Pantos, D. (2018). High-yielding synthesis of chiral donor–acceptor catenanes. Journal of Organic Chemistry, 83(19), 11654-11660. https://doi.org/10.1021/acs.joc.8b01629