Abstract
6-Monotosyl-and 6-mononaphthyl derivatives of β-cyclodextrin have been synthesized, and their self-association abilities have been compared. The quasi-elastic light-scattering study revealed the occurrence of self-organization of mono-6-naphtyl-β-cyclodextrin in dilute aqueous solutions that is responsible for the formation of nanosized aggregates. It is suggested that the driving forces of self-organization are the combination of hydrophobic interactions between the aromatic group of one cyclodextrin molecule and the cavity of the neighboring macrocycle that lead to the formation of noncovalent polymers and hydrogen bonds between these polymers. The absence of intermolecular interactions in the case of mono-6-tosyl-β-cyclodextrin is apparently related to the discrepancy between sizes of the tosyl moiety and of the β-cyclodextrin cavity. The influence of concentration, temperature, pH of solution, and competing low-molecular-mass agents on the self-assembly and stability of supramolecular polymers has been studied.
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