Tetra-porphyrin molecular tweezers: Two binding sites linked: Via a polycyclic scaffold and rotating phenyl diimide core
Date
2016
Authors
Murphy, R.B.
Norman, R.E.
White, J.M.
Perkins, M.V.
Johnston, M.R.
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Organic and Biomolecular Chemistry, 2016; 14(37):8707-8720
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Abstract
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.
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Copyright The Royal Society of Chemistry 2016