Synthesis of C3-symmetric tri(alkylamino) guests and their interaction with cyclodextrins

0440000 - ÚMCH 2016 RIV NL eng J - Článek v odborném periodiku
Bednaříková, T. - Tošner, Z. - Horský, Jiří - Jindřich, J.
Synthesis of C3-symmetric tri(alkylamino) guests and their interaction with cyclodextrins.
Journal of Inclusion Phenomena and Macrocyclic Chemistry. Roč. 81, 1-2 (2015), s. 141-152. ISSN 0923-0750. E-ISSN 1573-1111
Institucionální podpora: RVO:61389013
Klíčová slova: cyclodextrin * supramolecular interactions * C3-symmetric guests
Kód oboru RIV: CB - Analytická chemie, separace
Impakt faktor: 1.253, rok: 2015

The 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.
Trvalý link: http://hdl.handle.net/11104/0244997