Superstructures of fluorescent cyclodextrin via click-reaction

• Main Authors: Arkadius Maciollek, Helmut Ritter, Rainer Beckert
• Format: Article
• Language: English
• Published: Beilstein-Institut 2013-04-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: fluorescent dye; cyclodextrins; host–guest interaction; supramolecular polymer
• Online Access: https://doi.org/10.3762/bjoc.9.94

Mono-(6-azido-6-deoxy)-β-cyclodextrin (CD) was covalently attached to an alkyne-modified 5-methyl-2-(pyridin-2-yl)thiazol-4-ol yielding a fluorophore containing CD in a click-type reaction. Intermolecular complexes were formed by poly(host–guest)-interactions. The supramolecular structures were characterized by 1H NMR-ROESY spectroscopy, dynamic light scattering, UV–vis spectroscopy, fluorescence spectroscopy, and asymmetric flow field-flow fractionation. By adding potassium adamantane-1-carboxylate, the thiazol dye is displaced from the CD-cavity and the elongated noncovalent polymeric structures collapse.