Anion-controlled assembly of porphyrin-bicyclic guanidine conjugates.
[reaction: see text] Cationic porphyrins 1-3 bearing one, two, and four bicyclic guanidines form highly ordered chiral assemblies in aqueous solutions. The chirality is controlled by the type of the anionic counterpart and results from a spontaneous process. The chiral assemblies of 1-3 relate structurally to the complexes of achiral porphyrins with helical DNA. However, the presence of a chiral template (DNA, poly L-Glu were tested) is not necessary for formation of these specific chiral porphyrin assemblies.
Král
Vladimír
V
Department of Organic Chemistry and Biochemistry, Technical University of Munich, D-85747 Garching, Lichtenbergstrasse 4, Germany. schmidtchen@ch.tum.de
Schmidtchen
Franz P
FP
Lang
Kamil
K
Berger
Michael
M
D000838:Anions / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry; D006146:Guanidines / Q000737:chemistry*; D007202:Indicators and Reagents; D011166:Porphyrins / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet; D013698:Templates, Genetic
D000838:Anions; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006146:Guanidines; D007202:Indicators and Reagents; D011166:Porphyrins; D004247:DNA