TY - JOUR
T1 - A spectroscopic and structural study on the solvent-promoted stereospecific self-assembly of new Porphyrin-Bile Salt conjugates
AU - D'Annibale, Valeria
AU - Piccirillo, Luca
AU - Pacini, Beatrice
AU - Sennato, Simona
AU - Marconi, Claudia
AU - Del Giudice, Alessandra
AU - di Gregorio, Maria Chiara
AU - Schillén, Karin
AU - D'Abramo, Marco
AU - D'Annibale, Andrea
AU - Monti, Donato
AU - Galantini, Luciano
N1 - Publisher Copyright:
© 2024 The Author(s)
PY - 2024/11/5
Y1 - 2024/11/5
N2 - The chiral bile salt sodium cholate has been covalently linked to tetra-aryl-porphyrins, conferring them an extrinsic chirality and obtaining new molecules with high tendency to aggregate in solution. The chirality transfer from the molecular to the nano- and meso-scale has been investigated by promoting the self-assembly of the conjugates balancing the ratio of aqueous/organic solvent mixtures and allowing a fine control of the dimensions and morphology of the final supramolecular architectures. The shift from elongated structures with helical ribbon features to monodisperse tubules or from tightly packed rolled sheets to wrapped scrolls was enabled by changing the solvent composition, with the possibility of forming tubular structures with a hollow cavity. From UV–Vis and Circular Dichroism (CD) spectroscopy the ability to self-assemble into J-type aggregates with a strong induction of supramolecular chirality was revealed, shedding light on a two-step process, with a fast monomer nucleation followed by a slow second step of further stereospecific chiral evolution. The results as a whole promote the new porphyrin-cholate conjugates as promising smart and easily tunable chiral materials for the design of stereoselective sensing devices.
AB - The chiral bile salt sodium cholate has been covalently linked to tetra-aryl-porphyrins, conferring them an extrinsic chirality and obtaining new molecules with high tendency to aggregate in solution. The chirality transfer from the molecular to the nano- and meso-scale has been investigated by promoting the self-assembly of the conjugates balancing the ratio of aqueous/organic solvent mixtures and allowing a fine control of the dimensions and morphology of the final supramolecular architectures. The shift from elongated structures with helical ribbon features to monodisperse tubules or from tightly packed rolled sheets to wrapped scrolls was enabled by changing the solvent composition, with the possibility of forming tubular structures with a hollow cavity. From UV–Vis and Circular Dichroism (CD) spectroscopy the ability to self-assemble into J-type aggregates with a strong induction of supramolecular chirality was revealed, shedding light on a two-step process, with a fast monomer nucleation followed by a slow second step of further stereospecific chiral evolution. The results as a whole promote the new porphyrin-cholate conjugates as promising smart and easily tunable chiral materials for the design of stereoselective sensing devices.
KW - Bile salts
KW - Chirality
KW - Porphyrin aggregates
KW - Supramolecular chemistry
U2 - 10.1016/j.colsurfa.2024.134507
DO - 10.1016/j.colsurfa.2024.134507
M3 - Article
AN - SCOPUS:85198010376
SN - 0927-7757
VL - 700
JO - Colloids and Surfaces A: Physicochemical and Engineering Aspects
JF - Colloids and Surfaces A: Physicochemical and Engineering Aspects
M1 - 134507
ER -