The fabrication of controlled supramolecular nanostructures via self-assembly of protoporphyrin IX (PPIX) was studied with enantiomerically pure l-arginine and d-arginine, and we have shown that stoichiometry controlled the morphology formed. The nanostructure morphology was mainly influenced by the delicate balance of π-π stacking interactions between PPIX cores, as well as H-bonding between the deprotonated acidic head group of PPIX with the guanidine head group of arginine. PPIX self-assembled with l-/d-arginine to create rose-like nanoflower structures for four equivalents of arginine that were 5-10 μm in length and 1-4 μm diameter.
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