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

Literature Information

Publication Date 2019-01-04
DOI 10.1039/C8OB02689K
Impact Factor 3.876
Authors

Fabrizio Caroleo, Manuela Stefanelli, Gabriele Magna, Mariano Venanzi, Roberto Paolesse, Simona Sennato, Marilena Carbone, Donato Monti


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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