A comparison of the host-guest inclusion complexes ...

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Title A comparison of the host-guest inclusion complexes of 1,8-ANS and 2,6-ANS in parent and modified cyclodextrins
Author(s) Brian D. Wagner, S. J. Fitzpatrick
Journal Journal of Inclusion Phenomena and Macrocyclic Chemistry
Date 2000
Volume 38
Issue 1-4
Start page 467
End page 478
Abstract The fluorescent molecules 1-anilinonaphthalene-8-sulfonate (1,8-ANS) and 2-anilinonaphthalene-6-sulfonate (2,6-ANS) are extremely sensitive to the polarity of their local environment, making them excellent probes for the study of heterogeneous systems, including cyclodextrin (CD) solutions. Both are only weakly fluorescent in a highly polar medium, such as water, but are extremely fluorescent in a relatively nonpolar medium, such as within a CD cavity. These two probes are isomers, with major structural differences: 1,8-ANS is much bulkier and more spherical, whereas 2,6-ANS is much more streamlined and rod-shaped. Thus, they show major differences in their formation of CD inclusion complexes. This is reflected both in the magnitude of the observed fluorescence enhancement upon CD inclusion, as well as in the value of the association constant for complex formation. The creation of a scale for each probe for their fluorescence in CDs relative to that in ethanol allows for direct comparisons to be made between the two probes. These results are obtained and compared for the host-guest inclusion complexes of 1,8-ANS and 2,6-ANS with six CDs: alpha, beta, gamma, and their hydroxypropylated analogs.

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