Skeleton-selective fluorescent chemosensor based on cyclodextrin bearing a 4-amino-7-nitrobenz-2-oxa-1,3-diazole moiety.

A new type of fluorescent chemosensor, based on modified cyclodextrins bearing the fluorophore unit NBD-amine, was prepared. One of these new chemosensors, NC0betaCD, is sensitive to adamantane and borneol derivatives, which have a comparatively spherical shape that fits the beta-CD cavity, but is not sensitive to bile acids, which are strongly bound by the native beta-CD. Even in the presence of a bile acid, NC0betaCD can detect 1-adamantanol. Another of this new type of chemosensors, NC0gammaCD, is sensitive to bile acids but not to adamantane derivatives. The response of the new type of chemosensors to a guest was an increase in the fluorescence intensity.