NDLI: Supramolecular Chirality in Solvent-Promoted Aggregation of Amphiphilic Porphyrin Derivatives: Kinetic Studies and Comparison between Solution Behavior and Solid-State Morphology by AFM Topography

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Supramolecular Chirality in Solvent-Promoted Aggregation of Amphiphilic Porphyrin Derivatives: Kinetic Studies and Comparison between Solution Behavior and Solid-State Morphology by AFM Topography

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Paolesse, Roberto De Rossi, Massimo Laguzzi, Giuseppe Venanzi, Mariano Stefanelli, Manuela Mancini, Giovanna Gatto, Emanuela Luvidi, Loredana Sorrenti, Alessandro Monti, Donato
Description	Author Affiliation: Monti D ( Dipartimento di Scienze e Tecnologie Chimiche, Università degli Studi di Roma, Tor Vergata, Via della Ricerca Scientifica 1, 00134 Rome, Italy. monti@stc.uniroma2.it)
Abstract	The solvent-promoted aggregation behavior of some amphiphilic porphyrin derivatives bearing chiral functionality in the form of a charged L-proline group has been investigated by UV/Vis, resonance light scattering, fluorescence and circular dichroism spectroscopy. The investigated macrocycles give rise to aggregates featuring supramolecular chirality with high ellipticity. Kinetic studies reveal peculiar differences in the fashion of aggregation, depending on the intimate nature of the chiral functionality, namely, cationic (nitrogen-quaternized L-proline, $3H_{2})$ or anionic (carboxylate residue, $6H_{2})$ group. Formation of anionic $6H_{2}$ aggregates shows a diffusion-limited kinetic behavior. AFM topography studies show formation of tighter globular structures. On the other hand, the corresponding $3H_{2}$ aggregates are formed by a cooperative, fractal-type decay, and appear as long-fibrous, looser structures. In the templated aggregation of $3H_{2}$ over preformed $6H_{2}$ aggregates, AFM images show formation of globular structures with reduced sizes, as a likely consequence of shorter interchromophore distances, due to favorable Coulombic interactions. The results obtained show an interesting parallelism between the solution behavior and the solid-state aggregate structures, corroborating the sergeant–soldier effect observed in the templated aggregation. The results presented give important insights for understanding the complex mechanisms involved in these issues, which are of key importance for the development of chiral supramolecular materials and stereoselective sensors and devices.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	3
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-01-18
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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