Cooperative nanoparticle H-type self-assembly of a bolaamphiphilic BODIPY derivative in aqueous medium. (16th October 2017)

• Record Type: Journal Article
• Authors: Rödle, Alexander; Lambov, Martin; Mück-Lichtenfeld, Christian; Stepanenko, Vladimir; Fernández, Gustavo
• Is Part Of: Polymer. Volume 128(2017)
• Page Start: 317
• Page End: 324
• Publication Date: 2017-10-16
• Subjects: Supramolecular chemistry -- Aqueous self-assembly -- BODIPY dyes -- Non-covalent interactions -- Amphiphilic systems; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2016.12.050
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: 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. Graphical abstract: 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. Highlights: 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.