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Di‐2,7‐pyrenidecaphyrin( and Its Bis‐Organopalladium Complexes: Synthesis and Chiroptical Properties

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A non-aromatic expanded carbaporphyrinoid, incorporating two built-in 2,7-pyrenylene moieties was synthesized. The intrinsically labile topographic structure was demonstrated by proton-triggered conformational changes between the figure-of-eight and quasi-Möbius conformers. Upon treatment with Pd(OAc) 2 , the reaction produces two bis-Pd II complexes with distinct coordination modes. Metal coordination serves to fix the oligopyrrolic macrocyclic frame-works with the net result that both bis-Pd II complexes could be resolved by chiral high-performance liquid chromatography (HPLC). The isolated enantiomers showed considerable configurational stability and persistent chiroptical properties as evidenced by the intense response in the circular dichroism (CD) spectra from 300-850 nm and the record high absorption dissymmetry factors ( g abs of up to 0.038) seen in the near-infrared spectral region. In addition, the mutual interconversion of the enantiomers was found to be stereospecific and to favor the more stable isomers in the presence of the weakly acidic solvent deuterated chloroform.

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