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New J. Chem., 2008,�32, 712 - 718, DOI: 10.1039/b715985d

Complexation of 6-(4-(toluidinyl)naphthalene-2-sulfonate by -cyclodextrin and linked -cyclodextrin dimers

Duc-Truc Pham, Philip Clements, Christopher J. Easton, John Papageorgiou, Bruce L. May and Stephen F. Lincoln

The complexation of 6-(4

-(toluidinyl)naphthalene-2-sulfonate, TNS^-, by

-cyclodextrin (

CD) and five linked

CD-dimers is characterized by UV-Vis, fluorescence and ¹H NMR spectroscopy. In aqueous phosphate buffer at pH 7.0, I = 0.10 mol dm^-3 and 298.2 K, TNS^- forms host�guest complexes with

CD of stoichiometry

CD�TNS^- {K₁ = [

CD�TNS^-]/([

CD][TNS^-]) = 3300 dm³ mol^-1} and

CD₂�TNS^- {K₂ = [

CD₂�TNS^-]/([

CD][

CD�TNS^-]) = 11 dm³ mol^-1} as shown by fluorescence studies. For N,N-bis((2^Adextrin)-S,3^AS)-3^A-deoxy-3^A-

-cyclodextrin)succinamide, 33

CD₂su, N-((2^AS,3^AS)-3^A-deoxy-3^A-

-cyclodextrin)N

-(6^A-deoxy-6^A-

-cyclodextrin)urea, 36

CD₂su, N,N-bis(6^A-deoxy-6^A-

-cyclodextrin)succinamide, 66

CD₂su, N-((2^AS,3^AS)-3^A-deoxy-3^A-

-cyclodextrin)-N

-(6^A-deoxy-6^A-

-cyclodextrin)urea, 36

CD₂ur, and N,N-bis(6^A-deoxy-6^A-

-cyclodextrin)urea, 66

CD₂ur, the analogous K₁ = 9600, 8700, 12 500, 9800, and 38 000 dm³ mol^-1, respectively. ¹H NMR ROESY studies provide evidence for variation of the mode of complexation of the TNS^- guest as the host is changed. The factors affecting complexation are discussed and the synthesis of the new linked

CD-dimer 36

CD₂su is reported.

Graphical abstract image for this article (ID: b715985d)