Synthesis and solvent driven self-aggregation studies of meso-"C-glycoside"-porphyrin derivatives.
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.
Stepánek
Petr
P
Institute of Organic Chemistry and Biochemistry, AS CR, Flemingovo nám. 2, CZ-166 10, Praha 6, Czech Republic.
Dukh
Mykhaylo
M
Saman
David
D
Moravcová
Jitka
J
Kniezo
Ladislav
L
Monti
Donato
D
Venanzi
Mariano
M
Mancini
Giovanna
G
Drasar
Pavel
P
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D002942:Circular Dichroism; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008027:Light; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D012542:Scattering, Radiation; D012997:Solvents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014269:Trifluoroacetic Acid
D000447:Aldehydes; D006027:Glycosides; D011166:Porphyrins; D011758:Pyrroles; D012997:Solvents; D014269:Trifluoroacetic Acid