Synthesis and applications of dipyrromethenes

This proposal details the design, synthesis, characterization and application of homochiral dipyrromethene helicates, ideal candidates for use in applications that exploit optical and coordinative phenomena, e.g. chiral polymers, chiroptical switches, responsive surfactants, and catalysts. Dipyrromethenes have traditionally been synthetic precursors to porphyrins, although some chelation studies have been reported. With work in the Thompson group and elsewhere (primarily Germany, Japan, and the USA), the dipyrromethene moiety is emerging as an intriguing conjugated ligand skeleton that gives complexes possessing unique physicochemical properties. Researchers in the Thompson group are world leaders in the diastereoselective synthesis of dipyrromethene-based helicates, and are well-placed to harness the potential of such complexes through the exploitation of optical and physical characteristics (e.g. circular dichroism, UV-visible spectroscopy, fluorescence spectroscopy, solution- and solid-state NMR spectroscopy, HPLC, X-ray structure), as well as reactivity (e.g. coordination, self-assembly). Securing a fundamental understanding of the structure and properties of dipyrromethene helicates is crucial to all aspects of this research programme.The expertise of the Thompson laboratory lies in the synthesis and characterization of heterocycles. Synthetic chemistry involving dipyrromethenes is often very challenging, as the pyrrolic unit is highly reactive and can be difficult to handle during the preparation of complex molecules. Researchers trained in the Thompson group develop excellent synthetic chemistry skills. Careful and skilled mentoring ensures that current/future goals and expectations are met, that interest and motivation remains high, and that students strive to achieve their best at all times.