Preparation of cyclodextrin derivatives usable for modifications of solid surfaces

This master thesis deals with preparation of cyclodextrin (CD) derivatives that are suitable for bonding on solid surfaces such as dopamine polymer and gold. The nucleophilic attack of 6I -O-p-toluenesulfonyl--CD (6-tosyl-β-CD) by dithiols created derivatives with substituents bound to CD skeleton by one of the sulphur atom while keeping a free terminal sulphanyl group. Despite initial problems caused by oxidation of the thiols to disulfides, CDs were modified by alkyl or oligoethylene glycol spacers prepared in 60 - 88% yields. The same reaction was used for preparation of derivatives of β-CD with amino group at the end of the tether that was linked to CD by nitrogen atom. For these purposes were used corresponding diamines and reactions proceeded smoothly reaching up to 92% isolated yield. Next, also the chemoselectivity of the reaction with an ambident spacer bearing both amino and sulphanyl functional group was studied and by 2D NMR experiments was proved that substituent was bound to CD through sulphur atom. It was demonstrated on the case of preparation of CD derivative with dimethylene linker that was prepared in 84% yield. A complete set of yet other CD-oligoethylene glycol derivatives with spacers linked to CD skeleton through the sulphur atom and terminated by amino group was prepared by..