The ‘lock and key’ substrate binding by enzymes (Fig. 1A) has inspired the design of numerous supramolecular devices, sensors, and catalysts. In nature, the precise arrangement of binding groups, such as hydrogen bond donors and acceptors, is required to successfully bind a specific substrate. In enzymes, this is achieved through peptide primary and secondary structure and protein folding. Artificial enzyme mimics and related bioinspired systems employ predesigned organic scaffolds capable of supporting non-covalent interactions.<br/>As aromatic tetrapyrrolic macrocycles, porphyrins (Fig. 1B) are attractive targets in supramolecular chemistry and have been shown to bind anions, cations, and a wide range of neutral molecules. The sensing ability of porphyrin-based receptors can be adjusted and enhanced through core and peripheral functionalizations, leading to systems with diverse shapes, functions, and applicability.<br/>Inspired by nature, we re-engineered the porphyrin core to access new binding sites for small molecules and explore the full potential of the N4 cavity as a binding pocket. In this work selected porphyrin-based receptors and their supramolecular complexes with small organic molecules will be presented and the binding mechanisms will be discussed. The properties of these enzyme-like systems will be explored.

Porphyrins as versatile receptors for molecular recognition

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