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  • Title: Synthesis, chiroptical properties, and solid-state structure determination of two new chiral dipyrrin difluoroboryl chelates.
    Author: Gossauer A, Nydegger F, Kiss T, Sleziak R, Stoeckli-Evans H.
    Journal: J Am Chem Soc; 2004 Feb 18; 126(6):1772-80. PubMed ID: 14871109.
    Abstract:
    Two new types of optically active BODIPY fluorophores bearing chiral phenyl substituents either at the meso-position or at both external alpha-positions have been synthesized. Their chiroptical properties are strongly dependent both on the position of the chiral group and on the protonation of the chromophore. The solid-state structures of one of the difluoroboryl chelates bearing the chiral phenyl substituent at the meso-position (9a) as well as of the corresponding ligand (8a) and its perchlorate have been determined by X-ray diffraction analysis. These are, to the best of our knowledge, the first crystal structures of a dipyrrin free base and of a dipyrrin salt which have been obtained by X-ray diffraction analysis. Hence, for the first time, the helical structure of a protonated dipyrrin chromophore has been proved experimentally.
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