Abstract
The fluorescent molecules1-anilinonaphthalene-8-sulfonate (1,8-ANS) and2-anilinonaphthalene-6-sulfonate (2,6-ANS) areextremely sensitive to the polarity of their localenvironment, making them excellent probes for thestudy of heterogeneous systems, including cyclodextrin(CD) solutions. Both are only weakly fluorescent in ahighly polar medium, such as water, but are extremelyfluorescent in a relatively nonpolar medium, such aswithin a CD cavity. These two probes are isomers, withmajor structural differences: 1,8-ANS is much bulkierand more spherical, whereas 2,6-ANS is much morestreamlined and rod-shaped. Thus, they show majordifferences in their formation of CD inclusioncomplexes. This is reflected both in the magnitude ofthe observed fluorescence enhancement upon CDinclusion, as well as in the value of the associationconstant for complex formation. The creation of ascale for each probe for their fluorescence in CDsrelative to that in ethanol allows for directcomparisons to be made between the two probes. Theseresults are obtained and compared for the host-guestinclusion complexes of 1,8-ANS and 2,6-ANS with sixCDs: α, β, γ, and theirhydroxypropylated analogs.
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Wagner, B.D., Fitzpatrick, S.J. A Comparison of the Host–Guest Inclusion Complexes of 1,8-ANS and 2,6-ANS in Parent and Modified Cyclodextrins. Journal of Inclusion Phenomena 38, 467–478 (2000). https://doi.org/10.1023/A:1008198825835
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DOI: https://doi.org/10.1023/A:1008198825835