Issue 6, 2007
From the journal:

Organic & Biomolecular Chemistry

Synthesis and solvent driven self-aggregation studies of meso-“C-glycoside”-porphyrin derivatives†

Petr Štěpánek,a   Mykhaylo Dukh,a   David Šaman,a   Jitka Moravcová,b   Ladislav Kniežo,b   Donato Monti,c   Mariano Venanzi,c   Giovanna Mancinid  and  Pavel Drašar*ab  

* Corresponding authors

a Institute of Organic Chemistry and Biochemistry, AS CR, Flemingovo nám. 2, Praha 6, Czech Republic
E-mail: Pavel.Drasar@vscht.cz

b Institute of Chemical Technology, Technická 5, Praha 6, Czech Republic

c Dipartimento di Scienze e Tecnologie Chimiche, Univ. Roma “Tor Vergata”, Rome, Italy

d IMR-CNR, c/o Dip. Chim., Univ. Roma “La Sapienza”, Rome, Italy

Abstract

New types of porphyrin derivatives bearing “C-glycoside” moieties, either in 5,10,15,20- or in 5,15-meso-positions, were prepared and fully characterized. The presence of the glycosidic groups imparts to the title macrocycles, besides an amphiphilic character, a clear tendency to form chiral suprastructures upon solvent-driven self-aggregation in different aqueous–organic solvent mixtures. Supra-assembly phenomena, in terms of the size and morphology of the resulting structures, as well as their kinetics of aggregation, were studied by UV-visible, fluorescence, resonance light scattering (RLS), and CD spectroscopy, indicating that the morphology of the aggregates depends strongly on the structure of the porphyrin rings, and on the bulk conditions of aggregation.

Graphical abstract: Synthesis and solvent driven self-aggregation studies of meso-“C-glycoside”-porphyrin derivatives

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Article information

DOI
https://doi.org/10.1039/B616096D
Article type
Paper
Submitted
06 Nov 2006
Accepted
08 Jan 2007
First published
31 Jan 2007

Org. Biomol. Chem., 2007,5, 960-970

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Synthesis and solvent driven self-aggregation studies of meso-“C-glycoside”-porphyrin derivatives

P. Štěpánek, M. Dukh, D. Šaman, J. Moravcová, L. Kniežo, D. Monti, M. Venanzi, G. Mancini and P. Drašar, Org. Biomol. Chem., 2007, 5, 960 DOI: 10.1039/B616096D

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