title: Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers.
abstract: The fluorescent tagging of cyclodextrin derivatives enlarges their spectroscopic properties thus generating chemosensors, biological tools for visualization and sophisticated photoresponsive devices. Cyclodextrin polymers, due to the cooperative interactions, exhibit additional properties compared to their monomeric counterpart. These macromolecules can be prepared either in well water-soluble form or as gels of high swelling. Two versatile synthetic strategies for introducing a fluorescent tag (rhodamine, fluorescein, nitrobenzofuran or coumarin) into the water-soluble epichlorohydrin branched cyclodextrin polymers were worked out and compared. The fluorescent labeling was realized in three steps: 1) building in azido moieties, 2) transforming the azido groups into amino groups and 3) coupling the proper fluorescent compound to the amino groups. The other strategy started by functionalization of the monomer prior to the branching. Either the fluorescent-labeled monomer or the intermediate azido derivative of the monomer was branched. Further tuning of the properties of the polymer was achieved via branching of the methylated cyclodextrin derivative. The key intermediates and the fluorescent final products were characterized by various spectroscopic techniques and capillary electrophoresis. The applied synthetic routes were evaluated based on the molecular weight, cyclodextrin content of the products and the efficiency of labeling.
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: Milo
authors: M
authors: Malanga
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: Mihály
authors: M
authors: Bálint
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: István
authors: I
authors: Puskás
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: Kata
authors: K
authors: Tuza
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: Tamás
authors: T
authors: Sohajda
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: László
authors: L
authors: Jicsinszky
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: Lajos
authors: L
authors: Szente
authors: CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary.
authors: Éva
authors: É
authors: Fenyvesi
keywords: coumarin; fluorescein; functionalized monomers and polymers; nitrobenzofurazan; rhodamine