Spectroscopic, Morphological, and Mechanistic Investigation of the Solvent-Promoted Aggregation of Porphyrins Modified in meso-Positions by Glucosylated Steroids

0369950 - ÚEB 2012 RIV DE eng J - Journal Article
Zelenka, K. - Trnka, T. - Tišlerová, I. - Monti, D. - Cinti, S. - Naitana, M. L. - Schiaffino, L. - Venanzi, M. - Laguzzi, G. - Luvidi, L. - Mancini, G. - Nováková, Z. - Šimák, O. - Wimmer, Zdeněk - Drašar, P.
Spectroscopic, Morphological, and Mechanistic Investigation of the Solvent-Promoted Aggregation of Porphyrins Modified in meso-Positions by Glucosylated Steroids.
Chemistry - A European Journal. Roč. 17, č. 49 (2011), s. 13743-13753. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA MŠMT 2B06024
Institutional research plan: CEZ:AV0Z50380511
Keywords : aggregation * chirality * porphyrinoids
Subject RIV: CC - Organic Chemistry
Impact factor: 5.925, year: 2011

Solvent-driven aggregation of a series of porphyrin derivatives was studied by UV/Vis and circular dichroism spectroscopy. The porphyrins are characterised by the presence in the meso positions of steroidal moieties further conjugated with glucosyl groups. The presence of these groups makes the investigated macrocycles amphiphilic and soluble in aqueous solvent, namely, dimethyl acetamide/water. Aggregation of the macrocycles is triggered by a change in bulk solvent composition leading to formation of large architectures that express supramolecular chirality, steered by the presence of the stereogenic centres on the periphery of the macrocycles. The aggregation behaviour and chiroptical features of the aggregates are strongly dependent on the number of moieties decorating the periphery of the porphyrin framework. In particular, experimental evidence indicates that the structure of the steroid linker dictates the overall chirality of the supramolecular architectures.
Permanent Link: http://hdl.handle.net/11104/0203890