An overview of the solvent-driven aggregation of a series of chiral porphyrin derivatives studied by optical methods (UV/Vis, fluorescence, CD and RLS spectroscopies) is herein reported. The investigated porphyrins are characterized by the presence in the meso-positions of glycol-, steroidal- and glucosteroidal moieties, conferring amphiphilicity and solubility in aqueous media to the primarily hydrophobic porphyrin platform. Aggregation of the macrocycles is driven by a change in bulk solvent composition, forming architectures with supramolecular chirality, steered by the stereogenic centers on the porphyrin peripheral positions. The aggregation behavior and chiroptical properties of the final aggregated species strongly depend on the number and stereogenicity of the ancillary groups that dictate the mutual spatial arrangement of the porphyrin chromophores and their further organization in larger structures, usually detectable by different microscopies, such as AFM and SEM. Kinetic studies are fundamental to understand the aggregation mechanism, which is frequently found to be dependent on the substrate concentration. Additionally, Molecular Mechanics calculations can give insights into the intimate nature of the driving forces governing the self-assembly process. The critical use of these combined methods can shed light on the overall self-assembly process of chirally-functionalized macrocycles, with important implications on the development of chiral porphyrin-based materials.

Stefanelli, M., Mandoj, F., Magna, G., Lettieri, R., Venanzi, M., Paolesse, R., et al. (2020). The Self-aggregation of porphyrins with multiple chiral centers in organic/aqueous media: the case of sugar- and steroid-porphyrin conjugates. MOLECULES, 25(19), 4544 [10.3390/molecules25194544].

The Self-aggregation of porphyrins with multiple chiral centers in organic/aqueous media: the case of sugar- and steroid-porphyrin conjugates

Stefanelli, Manuela
;
Mandoj, Federica;Magna, Gabriele;Lettieri, Raffaella;Venanzi, Mariano;Paolesse, Roberto;Monti, Donato
2020-10-04

Abstract

An overview of the solvent-driven aggregation of a series of chiral porphyrin derivatives studied by optical methods (UV/Vis, fluorescence, CD and RLS spectroscopies) is herein reported. The investigated porphyrins are characterized by the presence in the meso-positions of glycol-, steroidal- and glucosteroidal moieties, conferring amphiphilicity and solubility in aqueous media to the primarily hydrophobic porphyrin platform. Aggregation of the macrocycles is driven by a change in bulk solvent composition, forming architectures with supramolecular chirality, steered by the stereogenic centers on the porphyrin peripheral positions. The aggregation behavior and chiroptical properties of the final aggregated species strongly depend on the number and stereogenicity of the ancillary groups that dictate the mutual spatial arrangement of the porphyrin chromophores and their further organization in larger structures, usually detectable by different microscopies, such as AFM and SEM. Kinetic studies are fundamental to understand the aggregation mechanism, which is frequently found to be dependent on the substrate concentration. Additionally, Molecular Mechanics calculations can give insights into the intimate nature of the driving forces governing the self-assembly process. The critical use of these combined methods can shed light on the overall self-assembly process of chirally-functionalized macrocycles, with important implications on the development of chiral porphyrin-based materials.
4-ott-2020
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/07 - FONDAMENTI CHIMICI DELLE TECNOLOGIE
Settore CHIM/02 - CHIMICA FISICA
English
Con Impact Factor ISI
chirality; circular dichroism; glycosylated compounds; nanostructures; porphyrins; solvodichroic effect; steroid derivatives; supramolecular chemistry
H2020-FETOPEN, 828779, INITIO project
https://www.mdpi.com/1420-3049/25/19/4544
Stefanelli, M., Mandoj, F., Magna, G., Lettieri, R., Venanzi, M., Paolesse, R., et al. (2020). The Self-aggregation of porphyrins with multiple chiral centers in organic/aqueous media: the case of sugar- and steroid-porphyrin conjugates. MOLECULES, 25(19), 4544 [10.3390/molecules25194544].
Stefanelli, M; Mandoj, F; Magna, G; Lettieri, R; Venanzi, M; Paolesse, R; Monti, D
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/255058
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