Preparation of γ-cyclodextrin derivatives usable for construction of self-assembled structures

This thesis is focused on the preparation of monosubstituted derivatives of -cyclodextrin ( -CD) which can form supramolecular polymers. These polymers can be utilized in capillary electrophoresis. Set of monosubstituted 2I -O-, 3I -O- a 6I -O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of -CD was prepared (naphthylallyl derivatives). Reaction was performed by cross metathesis of O-allyl derivatives of -CD with a 2-vinylnaphthalene in yields 16 - 25 %. Hoveyda-Grubbs 2nd generation catalyst was used. Alkylation of -CD with 2-(3-bromoprop-1-enyl)naphthalene followed by peracetylation of remaining hydroxyl groups and separation of isomers resulted in the per-O-acetyl-3I -O- a per-O- acetyl-6I -O-(3-(naphthalen-2-yl)prop-2-en-1-yl)- -CD in yields 5 and 1 %. A set of dimers of -CD 1,4-bis( -CD-2I -O-yl)-but-2-ene, 1,4-bis( -CD-3I -O-yl)-but-2-ene and 1,4-bis( - CD-6I -O-yl)-but-2-ene was prepared, too. Reaction was performed by cross metathesis of O-allyl derivatives of -CD in yields 1 - 8 % using again Hoveyda-Grubbs 2nd generation catalyst. The dimers of naphthalene guests (1,2-bis(naphthalen-2-yl)ethene and 1,2-bis(naphthalen-2-yl)ethane) for preparation of complexes with CD dimers were also prepared. Further optimization of synthesis of naphthylallyl derivatives of -CD was carried out. These..