Abstract
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.
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This work was supported by the Ministry of Education, Youth, and Sports of the Czech Republic (project No. MSM0021620857) and Grant Agency of the Czech Republic (project No. 13-01440S). Help of Dr. S. Filippov with ITC measurements is appreciated.
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Bednaříková, T., Tošner, Z., Horský, J. et al. Synthesis of C 3 -symmetric tri(alkylamino) guests and their interaction with cyclodextrins. J Incl Phenom Macrocycl Chem 81, 141–152 (2015). https://doi.org/10.1007/s10847-014-0443-1
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DOI: https://doi.org/10.1007/s10847-014-0443-1