Complexation and (Templated) Synthesis of Rhenium Complexes with Cyclodextrins and Cyclodextrin Dimers in Water

• Published in: Chemistry : a European journal 2001-08, Vol.7 (16), p.3603-3615
• Main Authors: van Bommel, Kjeld J. C., de Jong, Menno R., Metselaar, Gerald A., Verboom, Willem, Huskens, Jurriaan, Hulst, Ron, Kooijman, Huub, Spek, Anthony L., Reinhoudt, David N.
• Format: Article
• Language: English
• Subjects: Carbohydrate Conformation; cyclodextrins; Cyclodextrins - chemistry; Dimerization; Indicators and Reagents; Kinetics; Models, Molecular; Molecular Conformation; Nuclear Magnetic Resonance, Biomolecular; radiopharmaceuticals; Rhenium; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; supramolecular chemistry; templated synthesis; Water
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/1521-3765(20010817)7:16<3603::AID-CHEM3603>3.0.CO;2-E

Several small, lipophilic rhenium complexes form inclusion complexes with native β‐cyclodextrin (β‐CD) and β‐CD dimers. Association constants larger than 109 M−1 were obtained using dimers. The use of β‐CD also enabled the synthesis of these rhenium complexes in water, in excellent yields, through complexation of the otherwise insoluble corresponding ligands. The influence of the reaction time and temperature on the configuration of the reaction products has been investigated in depth for one of these complexes. Using a β‐CD dimer, it proved possible to specifically template the formation of one configuration. The strength of the complexes of the rhenium complexes in cyclodextrin dimers may allow radiolabeling of biomolecules. Lipophilic rhenium complexes can be synthesized in excellent yields in water by using β‐CD to solubilize the ligands. The influence of the reaction time and temperature on the complex configuration has been investigated in depth. Using a β‐CD dimer, it is possible to specifically template the formation of a single configuration (see figure).