Issue 5, 2019

Kinetic and spectroscopic studies on the chiral self-aggregation of amphiphilic zinc and copper (l)-prolinate-tetraarylporphyrin derivatives in different aqueous media

Abstract

The self-aggregation of inherently chiral, (L)-proline functionalised Cu and Zn porphyrin derivatives has been investigated in different aqueous organic solvent media. The results indicate that the title species form self-assembled structures expressing supramolecular chirality by the amplification of the stereochemical information stored on the L-prolinate functionality. A substantial difference of the aggregation modes, and the chiroptical features of the final supramolecular species for the two investigated complexes, is clearly imputable to the metal ions, having a different coordination ability toward solvent molecules. Detailed kinetic investigation performed by combining different spectroscopy techniques allowed the definition of the reaction mechanisms involved in these processes. The results described are of importance, for example, for the achievement of stereoselective devices and sensors.

Graphical abstract: Kinetic and spectroscopic studies on the chiral self-aggregation of amphiphilic zinc and copper (l)-prolinate-tetraarylporphyrin derivatives in different aqueous media

Supplementary files

Article information

Article type
Paper
Submitted
30 Oct 2018
Accepted
03 Jan 2019
First published
04 Jan 2019

Org. Biomol. Chem., 2019,17, 1113-1120

Kinetic and spectroscopic studies on the chiral self-aggregation of amphiphilic zinc and copper (L)-prolinate-tetraarylporphyrin derivatives in different aqueous media

F. Caroleo, M. Stefanelli, G. Magna, M. Venanzi, R. Paolesse, S. Sennato, M. Carbone and D. Monti, Org. Biomol. Chem., 2019, 17, 1113 DOI: 10.1039/C8OB02689K

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