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

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 81, Issue 1, 2015, Pages 141-152

  Bednaříková, Tereza ^a   Tosňer, Zdeněk ^a   Horský, Jiří ^b   Jindřich, Jindřich ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

Author keywords

C3 symmetric guests; Cyclodextrin; Inclusion complexes; Supramolecular interactions

Indexed keywords

EID: 85027930979     PISSN: 09230750     EISSN: 15731111     Source Type: Journal    
DOI: 10.1007/s10847-014-0443-1     Document Type: Article

References (22)

1. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743-1753 (1998)
2. Khan, A.R., Forgo, P., Stine, K.J., D'Souza, V.T.: Methods for selective modifications of cyclodextrins. Chem. Rev. 98, 1977-1996 (1998)
3. Fielding, L., McKellar, S.C., Florence, A.J.: Precision studies in supramolecular chemistry: a 1H NMR study of hydroxymethoxyacetophenone/β-cyclodextrin complexes. Magn. Reson. Chem. 49, 405-412 (2011)
4. Entrena, A., Jaime, C.: Cyclodextrin inclusion complexes. molecular mechanics calculations on the modification of p-face selectivity. J. Org. Chem. 62, 5923-5927 (1997)
5. Schneider, H.-J., Hacket, F., Rüdiger, V., Ikeda, H.: NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98, 1755-1785 (1998)
6. Tosňer, Z., Aski, S.N., Kowalewski, J.: Rotational dynamics of adamantanecarboxylic acid in complex with β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 55, 59-70 (2006)
7. Stojanov, M., Wimmer, R., Larsen, K.L.: Study of the inclusion complexes formed between cetirizine and α-, β-, and β-cyclodextrin and evaluation on their taste-masking properties. J. Pharm. Sci. 100, 3177-3185 (2011)
8. Guerrero-Martínez, A., Montoro, T., Viñas, M.H., Tardajos, G.: Complexation and chiral drug recognition of an amphiphilic phenothiazine derivative with β-cyclodextrin. J. Pharm. Sci. 97, 1484-1498 (2008)
9. Roik, N.V., Belyakova, L.A.: Thermodynamic, IR spectral and X-ray diffraction studies of the "β-cyclodextrin-para-aminobenzoic acid" inclusion complex. J. Incl. Phenom. Macrocycl. Chem. 69, 315-319 (2010)
10. Wenz, G., Han, B.-H., Müller, A.: Cyclodextrin Rotaxanes and Polyrotaxanes. Chem. Rev. 106, 782-817 (2006)
11. Harada, A., Takashima, Y., Yamaguchi, H.: Cyclodextrin-based supramolecular polymers. Chem. Soc. Rev. 38, 875-882 (2009)
12. Chen, Y., Zhang, Y.-M., Liu, Y.: Multidimensional nanoarchitectures based on cyclodextrins. Chem. Commun. 46, 5622-5633 (2010)
13. Ilioudis, C.A., Tocher, D.A., Steed, J.W.: A highly efficient, preorganized macrobicyclic receptor for halides based on ch and nh anion interactions. J. Am. Chem. Soc. 126, 12395-12402 (2004)
14. Han, W., Liu, C., Jin, Z.: Aerobic ligand-free suzuki coupling reaction of aryl chlorides catalyzed byin situ generated palladium nanoparticles at room temperature. Adv. Synth. Catal. 350, 501-508 (2008)
15. Kathiresan, M., Walder, L., Ye, F., Reuter, H.: Viologen-based benzylic dendrimers: selective synthesis of 3, 5-bis(hydroxymethyl) benzylbromide and conformational analysis of the corresponding viologen dendrimer subunit. Tetrahedron Lett. 51, 2188-2192 (2010)
16. Nakazaki, M., Yamamoto, K., Toya, T.: Syntheses and chemical characterization of tris-bridged [2.2.2]cyclophanes with a triphenylmethyl component. J. Org. Chem. 46, 1611-1615 (1981)
17. Wenz, G.: Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives. Beilstein J. Org. Chem. 8, 1890-1895 (2012)
18. Rekharsky, M.V., Inoue, Y.: Complexation Thermodynamics of Cyclodextrins. Chem. Rev. 98, 1875-1918 (1998)
19. Ernst, R.R., Bodenhausen, G., Wokaun, A.: Principles of nuclear magnetic resonance in one and two dimensions. Clarendon Press, Oxford (1990)
20. Nakazono, K., Takashima, T., Arai, T., Koyama, Y., Takata, T.: High-yield One-pot synthesis of permethylated a-cyclodextrinbased polyrotaxane in hydrocarbon solvent through an efficient heterogeneous reaction. Macromolecules 43, 691-696 (2010)
21. Iannazzo, L., Vollhardt, K.P.C., Malacria, M., Aubert, C., Gandon, V.: Alkynylboronates and-boramides in coi-and RhI-catalyzed [2 + 2+2] cycloadditions: construction of oligoaryls through selective suzuki couplings. Eur. J. Org. Chem. 2011, 3283-3292 (2011)
22. Brunel, J., Mongin, O., Jutand, A., Ledoux, I., Zyss, J., Blanchard-Desce, M.: Propeller-shaped octupolar molecules derived from triphenylbenzene for nonlinear optics: synthesis and optical studies. Chem. Mater. 15, 4139-4148 (2003)