Well-defined assemblies of adamantyl-terminated poly(propylene imine) dendrimers and ß-cyclodextrin in water

Michels, Jasper J. and Baars, Maurrice W.P.L. and Meijer, E.W. and Huskens, Jurriaan and Reinhoudt, David N. (2000) Well-defined assemblies of adamantyl-terminated poly(propylene imine) dendrimers and ß-cyclodextrin in water. Journal of the Chemical Society. Perkin transactions II, 2000 (9). pp. 1914-1918. ISSN 0300-9580

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Abstract:	Adamantyl-terminated poly(propylene imine) dendrimers 1–5 were dissolved in water in the presence of ß-cyclodextrin through strong non-covalent interaction between the ß-cyclodextrin and adamantyl groups. The solubilization of the dendrimer by ß-cyclodextrin is most effective at pH = 2, because at this pH there is complete protonation of the tertiary amino groups present in the dendritic cores, which causes the dendrimers to adopt a stretched conformation. The dendrimers remain in solution at pH <_7, but precipitate under basic conditions, except for 1, which remains in solution. The stoichiometries of the ß-cyclodextrin complexes of 1–4 at pH = 2 are 1·(ß-CD)4, 2·(ß-CD)8, 3·(ß-CD)16, and 4·(ß-CD)32, respectively. For steric reasons not all 64 adamantyl groups of 5 can be complexed by ß-cyclodextrin. The stoichiometry of the 5·(ß-CD)n complex is about 140 (pH = 2). Steric arguments confirm that the outer surface area of 5 is too small to allow complete coverage by ß-cyclodextrins. Qualitative fluorescence measurements at pH = 1 using 8-anilinonaphthalene-1-sulfonate (ANS) as a probe showed that the assemblies of 2–5 with ß-cyclodextrin act as supramolecular hosts for ANS in water. The binding of ANS is electrostatically driven and increases for higher generations.
Item Type:	Article
Copyright:	© 2008 Royal Society of Chemistry
Faculty:	Science and Technology (TNW)
Research Group:	Molecular Nanofabrication (MNF)
Link to this item:	http://purl.utwente.nl/publications/11754
Official URL:	http://dx.doi.org/10.1039/b002689l
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