Spectroscopic Study of (all-R,R)-cyclohexanohemicucurbit[8]uril and Its Host-Guest Supramolecular Hexafluorophosphate Complexes

Abstract

first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessAbstract Spectroscopic Study of (all-R,R)-cyclohexanohemicucurbit[8]uril and Its Host-Guest Supramolecular Hexafluorophosphate Complexes † by Nele Konrad *, Dzmitry Kananovich, Riina Aav and Victor Borovkov Department of Chemistry and Biotechnology, Tallinn University of Technology, 12616 Tallinn, Estonia * Author to whom correspondence should be addressed. † Presented at Symmetry 2017—The First International Conference on Symmetry, Barcelona, Spain, 16–18 October 2017. Proceedings 2018, 2(1), 64; https://doi.org/10.3390/proceedings2010064 Published: 3 January 2018 (This article belongs to the Proceedings of The First International Conference on Symmetry) Download Download PDF Download PDF with Cover Download XML Versions Notes (all-R,R)-Cyclohexanohemicucurbit[8]uril (cycHC[8]) is a chiral macrocycle binding anions [1] with 1:1 stoichiometry in protic solvents with the association constant of Ka = 3 × 104 M−1 in the case of the PF6 anion. Spectroscopic properties of cycHC[8] have been analysed by ultraviolet and circular dichroism spectroscopy exhibiting the corresponding electronic absorption. Host-guest complexation of cycHC[8] with the hexafluorophosphate anion containing chromophores was studied in different solvents. It was found that using ultraviolet, fluorescence and circular dichroism spectroscopies, it is possible to follow the supramolecular interaction between cycHC[8] and chromophore containing the hexafluorophosphate anion in methanol through the spectral changes of its cationic moiety. Furthermore, it was shown with circular dichroism that the cycHC[8] host uptakes the achiral hexafluorophosphate anion into its cavity, whilst the remaining chromophoric cation binds the cycHC[8]—anion complex via the corresponding electrostatic interactions. In the case of the chiral chromophoric guest, the effect of chiral discrimination is observed. The scope of chiral cations for enantio selectivity and achiral cations for chirality induction will be discussed. ReferenceKaabel, S.; Adamson, J.; Topić, F.; Kalenius, A.K.E.; Öeren, M.; Reimund, M.; Prigorchenko, E.; Lõokene, A.; Reich, H.J.; Rissanen, K.; et al. Chiral hemicucurbit[8]uril as an anion receptor: Selectivity to size, shape and charge distribution. Chem. Sci. 2017, 8, 2184–2190. [Google Scholar] [CrossRef] [PubMed]Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Share and Cite MDPI and ACS Style Konrad, N.; Kananovich, D.; Aav, R.; Borovkov, V. Spectroscopic Study of (all-R,R)-cyclohexanohemicucurbit[8]uril and Its Host-Guest Supramolecular Hexafluorophosphate Complexes. Proceedings 2018, 2, 64. https://doi.org/10.3390/proceedings2010064 AMA Style Konrad N, Kananovich D, Aav R, Borovkov V. Spectroscopic Study of (all-R,R)-cyclohexanohemicucurbit[8]uril and Its Host-Guest Supramolecular Hexafluorophosphate Complexes. Proceedings. 2018; 2(1):64. https://doi.org/10.3390/proceedings2010064 Chicago/Turabian Style Konrad, Nele, Dzmitry Kananovich, Riina Aav, and Victor Borovkov. 2018. "Spectroscopic Study of (all-R,R)-cyclohexanohemicucurbit[8]uril and Its Host-Guest Supramolecular Hexafluorophosphate Complexes" Proceedings 2, no. 1: 64. https://doi.org/10.3390/proceedings2010064 Find Other Styles Article Metrics No No Article Access Statistics Multiple requests from the same IP address are counted as one view.