Tetra-porphyrin molecular tweezers: two binding sites linked via a polycyclic scaffold and rotating phenyl diimide core
Norman, R E
White, J M
Perkins, Michael Victor
Johnston, Martin Ross
Royal Society of Chemistry
This journal is © The Royal Society of Chemistry 2016
The Royal Society of Chemistry
The synthesis of a tetra-porphyrin molecular tweezer with two binding sites is described. The bis-porphyrin binding sites are aligned by a polycyclic scaffold and linked via a freely rotating phenyl diimide core. Synthesis was achieved using a divergent approach employing a novel coupling method for linking two polycyclic units to construct the core, with a copper(II)-mediated phenyl boronic acid coupling found to extend to our polycyclic imide derivative. We expect this chemistry to be a powerful tool in accessing functional polycyclic supramolecular architectures in applications where north/south reactivity and/or directional interactions between modules are important. Porphyrin receptor functionalisation was undertaken last, by a four-fold ACE coupling reaction on the tetra-epoxide derivative of the core.
Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
tetra-porphyrin molecular tweezer, polycyclic scaffold, freely rotating phenyl diimide core
Murphy, R. B., Norman, R. E., White, J. M., Perkins, M. V., & Johnston, M. R. (2016). Tetra-porphyrin molecular tweezers: two binding sites linked via a polycyclic scaffold and rotating phenyl diimide core. Organic & Biomolecular Chemistry, 14(37), 8707-8720.