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• W2120554519 abstract "Abstract A series of bridged β‐cyclodextrin (β‐CyD) dimers possessing functional tethers of various lengths was synthesized in moderate yield by the treatment of 2,2′‐biquinoline‐ 4,4′‐dicarboxylic dichloride with β‐CyD or mono[6‐oligo(ethylenediamino)‐6‐deoxy]‐β‐CyDs. The products were 2,2′‐biquinoline‐4,4′‐dicarboxy‐bridged bis(6‐ O ‐β‐CyD) ( 8 ), N , N′ ‐bis(2‐aminoethyl)‐2,2′‐biquinoline‐4,4′‐dicarboxamide‐bridged bis(6‐amino‐6‐deoxy‐β‐CyD) ( 9 ), and N , N′ ‐bis(5‐amino‐3‐azapentyl)‐2,2′‐biquinoline‐4,4′‐dicarboxamide‐bridged bis(6‐amino‐6‐deoxy‐β‐CyD) ( 10 ). The reaction of 8 – 10 with copper perchlorate give their copper( II ) complexes 11 – 13 in satisfactory yields of over 77 %. All the bis(β‐CyD)s 8 – 13 act as efficient fluorescent sensors and display remarkable fluorescence enhancement upon addition of optically inert steroids. The inclusion complexation behaviors of 8 – 13 when treated with the representative steroids cholate ( 14 ), deoxycholate ( 15 ), and glycocholate ( 16 ) in aqueous solution at 25 °C were investigated by means of UV/Vis spectroscopy, conductivity and fluorescence measurements, circular dichroism spectroscopy, and 2D NMR spectroscopy. The tether length of bis(β‐CyD) 9 allows it to adopt a cooperative host–tether–guest binding mode in which the spacer and guest are co‐included in the two CyD cavities. As a result of this cooperation, 9 has a stability constant ( K s ) about 2×10 2 times higher than that of monomodified β‐CyD 4 for inclusion complexation with cholate. Metallooligo(β‐CyD)s with four β‐CyD units have enhanced binding abilities compared with monomodified β‐CyDs. These metallo compounds have binding affinities for guest steroids that are up to 50–4.1×10 3 times higher than those of CyDs 2 – 4 . The guest‐induced fluorescence enhancement of bis(CyD)s opens a new channel for the design of sensor materials. The complex stability constants of these compounds are discussed from the viewpoint of induced‐fit interaction and cooperative multiple binding between host and guest." @default.
• W2120554519 created "2016-06-24" @default.
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• W2120554519 date "2004-07-22" @default.
• W2120554519 modified "2023-10-11" @default.
• W2120554519 title "Biquinolino-Modifiedβ-Cyclodextrin Dimers and Their Metal Complexes as Efficient Fluorescent Sensors for the Molecular Recognition of Steroids" @default.
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• W2120554519 doi "https://doi.org/10.1002/chem.200305724" @default.
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