0000000000211696
AUTHOR
Elena Prigorchenko
showing 14 related works from this author
Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution
2017
A novel eight-membered macrocycle of the hemicucurbit[n]uril family, chiral (all-R)-cyclohexanohemicucurbit[8]uril (cycHC[8]) binds anions in a purely protic solvent with remarkable selectivity. The cycHC[8] portals open and close to fully encapsulate anions in a 1 : 1 ratio, resembling a molecular Pac-Man™. Comprehensive gas, solution and solid phase studies prove that the binding is governed by the size, shape and charge distribution of the bound anion. Gas phase studies show an order of SbF6− ≈ PF6− > ReO4− > ClO4− > SCN− > BF4− > HSO4− > CF3SO3− for anion complexation strength. An extensive crystallographic study reveals the preferred orientations of the anions within the octahedral cav…
Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril
2019
Amplification of a thermodynamically unfavoured macrocyclic product through the directed shift of the equilibrium between dynamic covalent chemistry library members is difficult to achieve. We show for the first time that during condensation of formaldehyde and cis-N,N'-cyclohexa-1,2-diylurea formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]) can be induced at the expense of thermodynamically favoured cis-cyclohexanohemicucurbit[6]uril (cis-cycHC[6]). The formation of i-cis-cycHC[6] is enhanced in low concentration of the templating chloride anion and suppressed in excess of this template. We found that reaction selectivity is governed by the solution-based template-a…
Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution
2017
A novel eight-membered macrocycle of the hemicucurbit[n]uril family, chiral (all-R)-cyclohexanohemicucurbit[8]uril (cycHC[8]) binds anions in a purely protic solvent with remarkable selectivity. The cycHC[8] portals open and close to fully encapsulate anions in a 1 : 1 ratio, resembling a molecular Pac-Man™. Comprehensive gas, solution and solid phase studies prove that the binding is governed by the size, shape and charge distribution of the bound anion. Gas phase studies show an order of SbF6− ≈ PF6− > ReO4− > ClO4− > SCN− > BF4− > HSO4− > CF3SO3− for anion complexation strength. An extensive crystallographic study reveals the preferred orientations of the anions within the octahedral cav…
Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril
2015
Enantiomerically pure cyclohexylhemicucurbit[8]uril (cycHC[8]), possessing a barrel-shaped cavity, has been prepared in high yield on a gram scale from either (R,R,N,N')-cyclohex-1,2-diylurea and formaldehyde or cycHC[6]. In either case, a dynamic covalent library is first generated from which the desired cycHC can be amplified using a suitable anion template.
Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution† †Electronic supplementary information (ESI) avai…
2016
Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.
CCDC 1569570: Experimental Crystal Structure Determination
2019
Related Article: Elena Prigorchenko, Sandra Kaabel, Triin Narva, Anastassia Baškir, Maria Fomitšenko, Jasper Adamson, Ivar Järving, Kari Rissanen, Toomas Tamm, Riina Aav|2019|Chem.Commun.|55|9307|doi:10.1039/C9CC04990H
CCDC 1514740: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A
CCDC 1514737: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A
CCDC 1514738: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A
CCDC 1514739: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A
Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution
2023
Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.
CCDC 1521388: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A
CCDC 1514736: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A
CCDC 1514741: Experimental Crystal Structure Determination
2016
Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A