Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
Nador, Fabiana (Institut Català de Nanociència i Nanotecnologia)
Wnuk, Karolina (Institut Català de Nanociència i Nanotecnologia)
Roscini, Claudio (Institut Català de Nanociència i Nanotecnologia)
Solorzano Rodríguez, Ruben (Institut Català de Nanociència i Nanotecnologia)
Faraudo, Jordi (Institut de Ciència de Materials de Barcelona)
Ruiz-Molina, Daniel (Institut Català de Nanociència i Nanotecnologia)
Novio Vázquez, Fernando (Institut Català de Nanociència i Nanotecnologia)

Date:	2018
Abstract:	The synthesis and structuration of a novel low-molecular-weight amphiphilic catechol compound is reported. The combination of a hydrophilic tail containing a catechol unit and a pyrene-based hydrophobic head favors solvent-tuned supramolecular assembly. Formation of hollow nanocapsules/vesicles occurs in concentrated solutions of polar protic and nonprotic organic solvents, whereas a fibril-like aggregation process is favored in water, even at low concentrations. The emission properties of the pyrene moiety allow monitoring of the self-assembly process, which could be confirmed by optical and electronic microscopy. In organic solvents and at low concentrations, this compound remains in its nonassembled monomeric form. As the concentration increases, the aggregation containing preassociated pyrene moieties becomes more evident up to a critical micellar concentration, at which vesicle-like structures are formed. In contrast, nanosized twist beltlike fibers are observed in water, even at low concentrations, whereas microplate structures appear at high concentrations. The interactions between molecules in different solvents were studied by using molecular dynamics simulations, which have confirmed different solvent-driven supramolecular interactions.
Grants:	Ministerio de Economía y Competitividad MAT2015-70615-R Ministerio de Economía y Competitividad SEV-2015-0496 Ministerio de Economía y Competitividad SEV-2013-0295
Rights:	Aquest material està protegit per drets d'autor i/o drets afins. Podeu utilitzar aquest material en funció del que permet la legislació de drets d'autor i drets afins d'aplicació al vostre cas. Per a d'altres usos heu d'obtenir permís del(s) titular(s) de drets.
Language:	Anglès
Document:	Article ; recerca ; Versió sotmesa a revisió
Subject:	Catechol ; Fluorescence ; Self-assembly ; Supramolecular chemistry ; Vesicles
Published in:	Chemistry (Weinheim), Vol. 24, Issue 55 (October 2018) , p. 14724-14732, ISSN 1521-3765

DOI: 10.1002/chem.201802249
PMID: 29900601

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Catalan Institute of Nanoscience and Nanotechnology (ICN2)
Articles > Research articles
Articles > Published articles