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 |
DisciplineOrgaaninen kemiaOrganic Chemistry
© 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
ISSN Search the Publication Forum0002-7863
Dataset(s) related to the publicationhttps://pubs.acs.org/doi/suppl/10.1021/jacs.0c00722/suppl_file/ja0c00722_si_001.pdf
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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. ...
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