Gossauer Albert, Nydegger Freddy, Kiss Tibor, Sleziak Robert, Stoeckli-Evans Helen
Chemiedepartement der Universität, Ch. du Musée 9, CH-1700 Fribourg, Switzerland.
J Am Chem Soc. 2004 Feb 18;126(6):1772-80. doi: 10.1021/ja030542r.
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.
已经合成了两种新型的具有光学活性的BODIPY荧光团，它们在中位或两个外部α位带有手性苯基取代基。它们的手性光学性质强烈依赖于手性基团的位置以及发色团的质子化。通过X射线衍射分析确定了一种在中位带有手性苯基取代基的二氟硼螯合物（9a）以及相应配体（8a）及其高氯酸盐的固态结构。据我们所知，这些是通过X射线衍射分析获得的二吡咯游离碱和二吡咯盐的首批晶体结构。因此，首次通过实验证明了质子化二吡咯发色团的螺旋结构。
