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Issue 5, 2019
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Kinetic and spectroscopic studies on the chiral self-aggregation of amphiphilic zinc and copper (L)-prolinate-tetraarylporphyrin derivatives in different aqueous media

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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

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Publication details

The article was received on 30 Oct 2018, accepted on 03 Jan 2019 and first published on 04 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02689K
Citation: Org. Biomol. Chem., 2019,17, 1113-1120

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    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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