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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

2020Frontiers in Chemistry18 citationsDOIOpen Access PDF

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.

Topics & Concepts

PorphyrinSupramolecular chemistryChirality (physics)ChemistryEnantiomerStereospecificitySelf-assemblyStereoselectivityCovalent bondCombinatorial chemistryNanotechnologyStereochemistryMoleculePhotochemistryOrganic chemistryMaterials scienceCatalysisQuantum mechanicsNambu–Jona-Lasinio modelQuarkChiral symmetry breakingPhysicsPorphyrin and Phthalocyanine ChemistryMolecular Sensors and Ion DetectionSupramolecular Chemistry and Complexes
Porphyrins Through the Looking Glass: Spectroscopic and Mechanistic Insights in Supramolecular Chirogenesis of New Self-Assembled Porphyrin Derivatives | Litcius