Cooperative nanoparticle H-type self-assembly of a bolaamphiphilic BODIPY derivative in aqueous medium

We report the H-type self-aggregation of a new linear water-soluble BODIPY bolaamphiphile equipped with amide groups and oligoethylene glycol chains. Intermolecular π-π interactions, amide-based hydrogen bonds and hydrophobic interactions lead to a highly cooperative self-assembly process. Detailed...

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Bibliographic Details
Published in:Polymer (Guilford) 2017-10, Vol.128, p.317-324
Main Authors: Rödle, Alexander, Lambov, Martin, Mück-Lichtenfeld, Christian, Stepanenko, Vladimir, Fernández, Gustavo
Format: Article
Language:English
Subjects:
Amphiphilic systems
Aqueous chemistry
Aqueous self-assembly
BODIPY dyes
Chemical bonds
Hydrogen bonding
Hydrogen bonds
Hydrophobicity
Nanoparticles
NMR
Non-covalent interactions
Nuclear magnetic resonance
Self-assembly
Supramolecular chemistry
Water chemistry
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Summary:We report the H-type self-aggregation of a new linear water-soluble BODIPY bolaamphiphile equipped with amide groups and oligoethylene glycol chains. Intermolecular π-π interactions, amide-based hydrogen bonds and hydrophobic interactions lead to a highly cooperative self-assembly process. Detailed spectroscopic studies suggest that strong hydrophobic interactions are the driving force for a rotational displacement of the dye molecules within the stack in order to shield the hydrophobic π-system from water molecules. The so formed highly-ordered micellar structures have been further characterized by NMR, AFM, TEM, DLS studies and theoretical calculations. A new amide-containing bolaamphiphilic BODIPY dye has been synthesized and fully characterized. The self-assembly studies in water reveal a highly cooperative self-aggregation mechanism and the formation of micelles, driven by π-π interactions, amide-based hydrogen bonds and the hydrophobic effect. A further agglomeration of individual micelles to spherical nanoparticles is induced by CH-O interactions between the ambient hydrophilic oligoethyleneglycol chains. [Display omitted] •A new bolaamphiphilic BODIPY derivative with amide groups and peripheral glycol chains is described.•The system self-assembles in water into nanoparticle assemblies in a cooperative fashion.•Spectroscopic and theoretical studies reveal a face-to-face H-type stacking of the BODIPY dyes with a twisted dye arrangement.
ISSN:0032-3861
1873-2291
DOI:10.1016/j.polymer.2016.12.050