Selective Formation of S4- and T-Symmetric Supramolecular Tetrahedral Cages and Helicates in Polar Media Assembled via Cooperative Action of Coordination and Hydrogen-Bonds
Shi, Q., Zhou, X., Yuan, W., Su, X., Neniškis, A., Wei, X., Taujenis, L., Snarskis, G., Ward, J. S., Rissanen, K., de Mendoza, J., & Orentas, E. (2020). Selective Formation of S4- and T-Symmetric Supramolecular Tetrahedral Cages and Helicates in Polar Media Assembled via Cooperative Action of Coordination and Hydrogen-Bonds. Journal of the American Chemical Society, 142(7), 3658-3670. https://doi.org/10.1021/jacs.0c00722
Published inJournal of the American Chemical Society
Wei, Xin |
© 2020 American Chemical Society
We report on the synthesis and self-assembly study of novel supramolecular monomers encompassing quadruple hydrogen-bonding motifs and metal coordinating 2,2’-bipyridine units. When mixed with metal ions such as Fe2+ or Zn2+, the tetrahedron cage complexes are formed in quantitative yields and full diastereoselectivity, even in highly polar acetonitrile or methanol solvents. The symmetry of the complexes obtained has been shown to depend critically on the flexibility of the ligand. Restriction of the rotation of the hydrogen-bonding unit with respect to the metal coordinating site results in a T-symmetric cage, whereas by introducing flexibility either through a methylene linker or rotating benzene ring allows the formation of S4-symmetric cages with self-filled interior. In addition, the possibility to select between tetrahedral cages or helicates, and to control the dimensions of the aggregate, has been demonstrated with three component assembly using external hydrogen-bonding molecular inserts or by varying the radius of the metal ion (Hg2+ vs Fe2+). Self-sorting studies of individual Fe2+ complexes of with ligands of different sizes revealed their inertness toward ligand scrambling. ...
PublisherAmerican Chemical Society
Dataset(s) related to the publicationhttps://pubs.acs.org/doi/suppl/10.1021/jacs.0c00722/suppl_file/ja0c00722_si_001.pdf
Publication in research information system
MetadataShow full item record
Additional information about fundingQ. S. acknowledges the financial support from the Natural Science Foundation of Jiangsu Province (BK20181375), Nanjing Tech University (Start-up Grant 39837129) and the State Key Laboratory of Fine Chemicals (KF1707). Q. S. is indebted to SICAM Fellowship from Jiangsu National Synergetic Innovation Center for Advanced Materials for financial support. A. N. acknowledges the PhD scholarship from Research Council of Lithuania. The authors thank Dr Rong Zhang for the initial attempt of HRMS. ...
Showing items with similar title or keywords.
Synthesis of C2-Symmetrical Bis-(β-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and Bis-(Pyran-2,4-diones) Derivatives Boraei, Ahmed T. A.; Haukka, Matti; Sarhan, Ahmed A. M.; Soliman, Saied M.; Al-Majid, Abdullah Mohammed; Barakat, Assem (MDPI AG, 2021)The synthesis of C2-symmetrical bis(β-enamino-pyran-2,4-dione) derivative 3 connected via 1,6-hexylene linker was reported for the first time. X-ray structures and Hirshfeld studies of the new bis- β-enamino-pyran-2,4-dione ...
Cocrystal trimorphism as a consequence of the orthogonality of halogen- and hydrogen-bonds synthons Topić, Filip; Lisac, Katarina; Arhangelskis, Mihails; Rissanen, Kari; Cinčić, Dominik; Friščić, Tomislav (Royal Society of Chemistry, 2019)True trimorphic cocrystals, i.e. multi-component molecular crystals of identical composition that exhibit three polymorphic structures, are exceedingly rare and so far no halogen-bonded cocrystal system has been reported ...
Hydrogen and Halogen Bond Mediated Coordination Polymers of Chloro-Substituted Pyrazin-2-Amine Copper(I) Bromide Complexes Mailman, Aaron; Puttreddy, Rakesh; Lahtinen, Manu; Svahn, Noora; Rissanen, Kari (MDPI AG, 2020)A new class of six mono- (1; 3-Cl-, 2; 5-Cl-, 3; 6-Cl-) and di-(4; 3,6-Cl, 5; 5,6-Cl-, 6; 3,5-Cl-) chloro-substituted pyrazin-2-amine ligands (1–6) form complexes with copper (I) bromide, to give 1D and 2D coordination ...
Synthetic and Structural Studies on the Effect of Non-Covalent Interactions on N(sp2)-Heterocyclic Molecules Taipale, Essi (2022)The thesis herein describes the synthesis and characterization of compounds designed to be utilized as acceptor molecules in non-covalent interactions. The non-covalent interactions are applied in fluorescence modulation ...
Subcomponent self‐assembly of a cyclic tetranuclear Fe(II) helicate in a highly diastereoselective self‐sorting manner Anhäuser, Jana; Puttreddy, Rakesh; Glanz, Lukas; Schneider, Andreas; Engeser, Marianne; Rissanen, Kari; Lützen, Arne (Wiley-VCH Verlag, 2019)An enantiomerically pure diamine based on the 4,15‐difunctionalized [2.2]paracyclophane scaffold and 2‐formylpyridine self‐assemble into an optically pure cyclic metallosupramolecular Fe₄L₆ helicate upon mixing with iron(II) ...