A non-aromatic expanded carbaporphyrinoid, incorporating two built-in 2,7-pyrenylene moieties was synthesized. The intrinsically labile 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 macrocyclic frameworks with the net result that both bis-Pd II complexes could be resolved by high performance liquid chromatography (HPLC) on a chiral stationary phase. The isolated enantiomers showed persistent chiroptical properties as evidenced by the intense response in the circular dichroism (CD) spectra and the record high absorption dissymmetry factors (g abs of up to 0.038) seen in the near-infrared spectral region. Moreover, the mutual interconversion of these two Pd II complexes was found to be stereospecific and to favor the more stable isomers under weakly acidic conditions.

We report a fully organic pyridine-tetrapyrrolic U-shaped acyclic receptor 10, which prefers a supramolecular pseudo-macrocyclic dimeric structure (10)2 in a less polar, non-coordinating solvent (e.g., CHCl3). Conversely, when it is crystalized from a polar, coordinating solvent (e.g., N,N-dimethylformamide, DMF), it exhibited an infinite supramolecular one-dimensional (1D) “zig-zag” polymeric chain, as inferred from the single-crystal X-ray structures. This supramolecular system acts as a potential receptor for strong acids, e.g., p-toluenesulfonic acid (PTSA), methane sulfonic acid (MSA), H2SO4, HNO3, and HCl, with a prominent colorimetric response from pale yellow to deep red. The receptor can easily be recovered from the organic solution of the host–guest complex by simple aqueous washing. It was observed that relatively stronger acids with pKa < −1.92 in water were able to interact with the receptor, as inferred from 1H NMR titration in tetrahydrofuran-d8 (THF-d8) and ultraviolet–visible (UV–vis) spectroscopic titrations in anhydrous THF at 298 K. Therefore, this new dynamic supramolecular receptor system may have potentiality in materials science research.

A non-aromatic expanded carbaporphyrinoid, incorporating two built-in 2,7-pyrenylene moieties was synthesized. The intrinsically labile 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 macrocyclic frameworks with the net result that both bis-Pd II complexes could be resolved by high performance liquid chromatography (HPLC) on a chiral stationary phase. The isolated enantiomers showed persistent chiroptical properties as evidenced by the intense response in the circular dichroism (CD) spectra and the record high absorption dissymmetry factors (g abs of up to 0.038) seen in the near-infrared spectral region. Moreover, the mutual interconversion of these two Pd II complexes was found to be stereospecific and to favor the more stable isomers under weakly acidic conditions.