Anion-driven encapsulation of cationic guests inside pyridinearene dimers
Kiesilä, A., Moilanen, J. O., Kruve, Anneli., Schalley, C. A., Barran, P., & Kalenius, E. (2019). Anion-driven encapsulation of cationic guests inside pyridinearene dimers. Beilstein Journal of Organic Chemistry, 15, 2486-2492. https://doi.org/10.3762/bjoc.15.241
Published inBeilstein Journal of Organic Chemistry
DisciplineOrgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaOrganic ChemistryInorganic and Analytical Chemistry
© 2019 The Authors
Pyridinearenes have previously been considered as anion binding hosts due to the electron-poor nature of the pyridine ring. Herein, we demonstrate the encapsulation of Me4N+ cations inside a dimeric hydrogen-bonded pyridinearene capsule, which contradicts with earlier assumptions. The complexation of a cationic guest inside the pyridinearene dimer has been detected and studied by multiple gas-phase techniques, ESI-QTOF-MS, IRMPD, and DT-IMMS experiments, as well as DFT calculations. The comparison of classical resorcinarenes with pyridinearenes by MS and NMR experiments reveals clear differences in their host–guest chemistry and implies that cation encapsulation in pyridinearene is an anion-driven process.
PublisherBeilstein Institut zur Foerderung der Chemischen Wissenschaften
ISSN Search the Publication Forum2195-951X
Dataset(s) related to the publicationhttps://www.beilstein-journals.org/bjoc/content/ supplementary/1860-5397-15-241-S1.pdf
Publication in research information system
MetadataShow full item record
Related funder(s)Academy of Finland
Funding program(s)Research costs of Academy Research Fellow, AoF; Academy Research Fellow, AoF; Postdoctoral Researcher, AoF
Additional information about fundingWe wish to thank The Academy of Finland (projects 284562, 278743 and 312514 to E.K. and 285855 to J.O.M.), the University of Jyväskylä and the Deutsche Forschungsgemeinschaft (Core Facility BioSupraMol) for financial support. J.O.M wishes to acknowledge Finnish Grid and Cloud Infrastructure (persistent identifier urn:nbn:fi:research-infras-2016072533), CSC - IT Center for Science, Finland, and Prof. Heikki M. Tuononen for computational resources. ...
Showing items with similar title or keywords.
Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles Helttunen, Kaisa; Salorinne, Kirsi; Barboza, Tahnie; Barbosa, Hélène Campos; Suhonen, Aku; Nissinen, Maija (Centre National de la Recherche Scientifique and The Royal Society of Chemistry, 2012)A group of seven resorcinarene bis-crown ethers (CNBC5) with two polyether bridges at the upper rim and either propyl, butyl, pentyl, heptyl, nonyl, decyl or undecyl groups at the lower rim were synthesized and their binding ...
Role of Alkyl Substituent and Solvent on the Structural, Thermal, and Magnetic Properties of Binary Radical Salts of 1,2,3,5-Dithia- or Diselenadiazolyl Cations and the TCNQ Anion Taponen, Anni I.; Ayadi, Awatef; Svahn, Noora; Lahtinen, Manu K.; Rouzières, Mathieu; Clérac, Rodolphe; Tuononen, Heikki M.; Mailman, Aaron (American Chemical Society (ACS), 2022)The synthesis, structural, thermal, and magnetic properties of a series of simple binary organic salts based on the radical anion of 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 4-(N-alkylpyridinium-3-yl)-1,2,3,5-dithiadiazolyl ...
Towards purely inorganic clusters in medicine : biocompatible divalent cations as counterions of cobaltabis(dicarbollide) and its iodinated derivatives Zaulet, Adnana; Nuez, Miquel; Sillanpää, Reijo; Teixidor, Francesc; Viñas, Clara (Elsevier, 2021)Monovalent cations, Cs+, and alkylammonium ([NR4]+) salts have traditionally been used to precipitate the anions of boranes, carborane and metallocarborane clusters. In contrast, in the body and in living organisms in ...
Encapsulation of xenon by bridged resorcinarene cages with high 129Xe NMR chemical shift and efficient exchange dynamics Komulainen, Sanna; Iresh Fernando, P. U. Ashvin; Mareš, Jiří; Selent, Anne; Khalili, Roya; Cesana, Paul T.; Ebeling, Andreas; Kantola, Anu M.; Beyeh, Ngong Kodiah; Rissanen, Kari; DeBoef, Brenton; Lantto, Perttu; Telkki, Ville-Veikko (Elsevier BV, 2023)Functionalized cages encapsulating xenon atoms enable highly sensitive, background-free molecular imaging through a technique known as HyperCEST 129Xe MRI. Here, we introduce a class of potential biosensor cage structures ...
Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands Anhäuser, J.; Puttreddy, Rakesh; Lorenz, Y.; Schneider, A.; Engeser, M.; Rissanen, Kari; Lützen, A. (Royal Society of Chemistry, 2019)Two constitutionally isomeric chiral bis(pyridine) ligands based on planar chiral 4,15-difunctionalized [2.2]paracyclophanes were synthesized, the respective enantiomers were separated via HPLC on a chiral stationary phase, ...