Synthesis of C 3 -symmetric tri(alkylamino) guests and their interaction with cyclodextrins

TitleSynthesis of C 3 -symmetric tri(alkylamino) guests and their interaction with cyclodextrins
Publication TypeJournal Article
Year of Publication2015
AuthorsBednaříková T, Tošner Z, Horský J, Jindřich J
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Pagination141 - 152
Date Published2015///
ISBN Number1388-3127, 1573-1111
KeywordsC 3 -symmetric guests, Crystallography, Cyclodextrin, duplicate, Food Science, INCLUSION COMPLEXES, Organic Chemistry, Supramolecular interactions
AbstractThe synthesis of a series of star-shaped C 3 -symmetric amines and their inclusion complexation properties toward α-, β-, γ-cyclodextrins and their permethylated derivatives has been described. The star molecules comprise of 1,3,5-trisubstited benzene core and the points formed by (alkylamino)methyl or 4-((alkylamino)methyl)phenyl groups. The modes of host–guest interaction were studied by UV–Vis spectroscopy, ITC, 1H NMR and 2D-NMR (NOESY). It was found that star molecules containing (tert-butylamino)methyl, (adamantan-1-ylamino)methyl, 4-((isopropylamino)methyl)phenyl, 4-((tert-butylamino)methyl)phenyl and protonated 4-((adamantan-1-ylamino)methyl)phenyl points form strong host–guest complexes with β-cyclodextrin. It was also proved that the largest C 3 -symmetric guest can form complexes with β-cyclodextrin with stoichiometry 3 which is required for construction of dendrimer supramolecular structures. None of the investigated amines forms a strong complex with permethylated cyclodextrins.
Short TitleJ. Incl. Phenom. Macrocycl. Chem.
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