Porphyrins and chlorins are aromatic heterocycles that are ubiquitous in nature where they are prosthetic groups in a large number of enzymes and light-harvesting proteins. Their large p-system allow these compounds to absorb light across the visible spectrum. The synthesis of porphyrin analogues is of interest because of the potential to fine-tune their optical properties. This is important for their use as photo-chemotherapeutics, optical labels, or light-harvesting dyes.We recently introduced a class of chlorin analogues in which the pyrrolidine moiety of a chlorin was replaced by a morpholine moiety. As their free bases and Ni(II) complexes, these morpholinochlorins possess helimeric chirality, opening up potential applications for these porphyrinoids in stereoselective molecular-recognition systems and chiral catalysis (J. Am. Chem. Soc. 2011  , 133, 8740�8752). We report here to which degree the conformation and optical properties of metallomorpholinochlorins is modulated by the type of metal coordinated to their central cavity. The conformations were deduced by X-ray single crystal diffraction.

Metallomorpholinochlorins: Mapping the conformational space of morpholinochlorins

243rd National Meeting (2012)

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