Secondary Face-to-Face 2–2′ β-Cyclodextrin Dimers Linked with Fluorescent Rigid Spacer Arms: A Cyclodextrin-Based Ratiometric Sensor for Bile Salts
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Martos Maldonado, Manuel Cristo![Autoridad Universidad de Almería Autoridad Universidad de Almería](/themes/Mirage2/images/autoridades/autoridad.png)
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Fecha
2012-04-23Resumen
The synthesis of a series of β-cyclodextrin (CD) dimers in which the two macrocycle units are linked by rigid-rod phenylene-ethynylene tethers of different length and shape through the cyclodextrin secondary sides is reported. The synthesis involves Sonogashira coupling reactions for construction of the tethers and final grafting of the CD units by click chemistry. The self-aggregation of the synthesized CD dimers in aqueous medium was investigated by fluorescence spectroscopy, isothermal titration calorimetry and dynamic light scattering. Rigid-rod-tethered cyclodextrin dimers formed polydisperse nanoparticles of 240 to 480 nm in water solution depending on the tether shape, and exhibited fluorescence. The binding and fluorescence sensing abilities of the CD dimers toward sodium cholate and deoxycholate were studied. As a result, the newly synthesized rigid-rod-tethered cyclodextrin dimers proved to be very sensitive fluorescent chemosensors. A new cyclodextrin-based ratiometric fluor...
Palabra/s clave
Cyclodextrin
Host-guest systems
Sensors
Fluorescent probes
Cross-coupling
Click chemistry