Chiral Enantioselective Assemblies Induced from Achiral Porphyrin by L- and D-Lysine.

Abstract

π-Conjugated porphyrins have aroused particular attention for nanofabrication and biomimics, however, little attention has been paid to porphyrins-based chiral analysis owing to the achiral feature of porphyrins. Here, we demonstrated a chiral self-assembly of achiral porphyrin induced by L- and D-lysine (L- and D-Lys), and the resultant porphyrin self-assembly exhibited alterable morphologies depending on the inducer used (L- or D-Lys). The supramolecular chirality of the self-assembly was characterized by circular dichroism (CD) spectra, confirming successful transfer of molecular chirality from L- and D-Lys to the self-assembly. The enantioselective property of the chiral self-assembly was also investigated by using tryptophan (Trp) isomers as the model, and the results indicated that the developed chiral self-assembly showed significantly higher affinity toward L-Trp than D-Trp. Also in this work, the L-/D-Lys induced chiral self-assembly of porphyrin and the supramolecular interaction between the self-assembly and L-/D-Trp were also studied by density functional theory (DFT).