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A spectroscopic and structural study on the solvent-promoted stereospecific self-assembly of new Porphyrin-Bile Salt conjugates

D'Annibale, Valeria LU ; Piccirillo, Luca ; Pacini, Beatrice ; Sennato, Simona ; Marconi, Claudia LU ; Del Giudice, Alessandra LU orcid ; di Gregorio, Maria Chiara ; Schillén, Karin LU orcid ; D'Abramo, Marco and D'Annibale, Andrea , et al. (2024) In Colloids and Surfaces A: Physicochemical and Engineering Aspects 700.
Abstract

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... (More)

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.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Bile salts, Chirality, Porphyrin aggregates, Supramolecular chemistry
in
Colloids and Surfaces A: Physicochemical and Engineering Aspects
volume
700
article number
134507
pages
13 pages
publisher
Elsevier
external identifiers
  • scopus:85198010376
ISSN
0927-7757
DOI
10.1016/j.colsurfa.2024.134507
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2024 The Author(s)
id
e096bc79-19b4-4666-8b69-9ceb05e514fb
date added to LUP
2024-07-19 22:18:57
date last changed
2025-04-04 14:12:57
@article{e096bc79-19b4-4666-8b69-9ceb05e514fb,
  abstract     = {{<p>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.</p>}},
  author       = {{D'Annibale, Valeria and Piccirillo, Luca and Pacini, Beatrice and Sennato, Simona and Marconi, Claudia and Del Giudice, Alessandra and di Gregorio, Maria Chiara and Schillén, Karin and D'Abramo, Marco and D'Annibale, Andrea and Monti, Donato and Galantini, Luciano}},
  issn         = {{0927-7757}},
  keywords     = {{Bile salts; Chirality; Porphyrin aggregates; Supramolecular chemistry}},
  language     = {{eng}},
  month        = {{11}},
  publisher    = {{Elsevier}},
  series       = {{Colloids and Surfaces A: Physicochemical and Engineering Aspects}},
  title        = {{A spectroscopic and structural study on the solvent-promoted stereospecific self-assembly of new Porphyrin-Bile Salt conjugates}},
  url          = {{http://dx.doi.org/10.1016/j.colsurfa.2024.134507}},
  doi          = {{10.1016/j.colsurfa.2024.134507}},
  volume       = {{700}},
  year         = {{2024}},
}