Porphyrins Through the Looking Glass: Spectroscopic and Mechanistic Insights in Supramolecular Chirogenesis of New Self-Assembled Porphyrin Derivatives

Manuela Stefanelli; Marco Savioli; Francesca Zurlo; Gabriele Magna; Sandra Belviso; Giulia Marsico; Stefano Superchi; Mariano Venanzi; Corrado Di Natale; Roberto Paolesse; Donato Monti

doi:10.3389/fchem.2020.587842

Porphyrins Through the Looking Glass: Spectroscopic and Mechanistic Insights in Supramolecular Chirogenesis of New Self-Assembled Porphyrin Derivatives

Front Chem. 2020 Oct 15:8:587842. doi: 10.3389/fchem.2020.587842. eCollection 2020.

Authors

Affiliations

¹ Department of Science and Chemical Technologies, University of Rome "Tor Vergata", Rome, Italy.
² Department of Sciences, University of Basilicata, Potenza, Italy.
³ Department of Electronic Engineering, University of Rome Tor Vergata, Rome, Italy.
⁴ Department of Chemistry, University La Sapienza, Rome, Italy.

Abstract

The solvent driven aggregation of porphyrin derivatives, covalently linked to a L- or D-prolinate enantiomer, results in the stereospecific formation of species featuring remarkable supramolecular chirality, as a consequence of reading and amplification of the stereochemical information stored in the proline-appended group. Spectroscopic, kinetic, and topographic SEM studies gave important information on the aggregation processes, and on the structures of the final chiral architectures. The results obtained may be the seeds for the construction of stereoselective sensors aiming at the detection, for example, of novel emergent pollutants from agrochemical, food, and pharmaceutical industry.

Keywords: chirality; circular dichroism; porphyrins; self-assembly; supramolecular chemistry; supramolecular chirogenesis.