Cyclodextrins diazonium salts

Diget, J. S., H. N. Petersen, H. Schaarup-Jensen, A. U. Sprensen, T. T. Nielsen, S. U. Pedersen, K. Daasbjerg, K. L. Larsen, and M. Hinge. Synthesis of P-cyclodextrin diazonium salts and electrochemical immobilization onto glassy carbon and gold surfaces. 

A similar template-directed approach was employed (Figure 31) by Anderson et al. [48] to self-assemble azo-dye [2]rotaxanes. The azobenzene diazonium salt 98 is bound by a-cyclodextrin 99 and also by / -cyclodextrin 100 in H20 with pseudorotaxane geometries. Reaction of the terminal diazonium functions with / -naphthol 101 affords the purple [2]rotaxanes 102 and 103 in yields of 12 and 15%, respectively. These two [2]rotaxanes were characterized by electrospray mass spectrometry which revealed peaks corresponding to the loss of all four sodium cations in both cases. By irradiating some of the protons of the dumbbellshaped components of these [2]rotaxanes, enhancement of the resonances of some of the cyclodextrin protons could be observed as a result of an intercomponent... 

Cyclodextrins form complexes with diazonium salts. Rates and product distribution for spontaneous dediazoniation of isomeric methylbenzenediazonium salts in the presence of a-, / -, and y-CD in aqueous acidic solution were found to be independent on acidity and CDs concentration [8], cf. [9],... 

Anderson el. al. [34] described rotaxanes of cyclodextrins with azo dyes that were synthesized by coupling of bis-diazonium salt 1 or 2 with water-soluble 2-naphthol derivative in the presence of a- or /J-cyclodcxtrin 3 (Figure 11). The products were isolated by paper chromatography. The yield for rotaxane 4 varied from 12 to 15 % for a- and fi-CD, respectively. 

Jamrogiewicz, M. Wagner-Wysiecka, E. Luboch, E. and Biemat, J.F. (2004) Effect of /3-cyclodextrin on coupling of diazonium salts, XXIX International Symposium on Macrocyclic Chemistry, Cairns, Australia, Abstracts, KL - ISMC - 9. 

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