Subcomponent self‐assembly of a cyclic tetranuclear Fe(II) helicate in a highly diastereoselective self‐sorting manner
Anhäuser, J., Puttreddy, R., Glanz, L., Schneider, A., Engeser, M., Rissanen, K., & Lützen, A. (2019). Subcomponent self‐assembly of a cyclic tetranuclear Fe(II) helicate in a highly diastereoselective self‐sorting manner. Chemistry : A European Journal, 25(33), 12294-12297. https://doi.org/10.1002/chem.201903164
Published inChemistry : A European Journal
© 2019 The Authors
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) ions in a diastereoselective subcomponent self‐assembly process. The cyclic assembly results from steric strain that prevents the formation of a smaller linear dinuclear triple‐stranded helicate, and hence, leads to the larger strain‐free assembly that fulfils the maximum occupancy rule. Interestingly, use of the racemic diamine also leads to a racemic mixture of the homochiral cyclic helicates as the major product in a highly diastereoselective narcissistic chiral self‐sorting manner given the fact that the assembly contains ten stereogenic elements which can in principle give rise to 149 different diastereomers. The metallosupramolecular aggregates could be characterized by NMR, UV‐Vis and CD spectroscopy, mass spectrometry and X‐ray crystallography.
Publication in research information system
MetadataShow full item record
Related funder(s)Academy of Finland
Funding program(s)Postdoctoral Researcher, AoF
Additional information about fundingAuthors acknowledge the Studienstiftung des deutschen Volkes for a doctoral scholarship and the Bonn International Graduate School of Chemistry for an international research scholarship (J.A.), the Academy of Finland (R.P.298817)and the University of Jyväskylä, Finland for the financial support.
Showing items with similar title or keywords.
Hexagonal Microparticles from Hierarchical Self-Organization of Chiral Trigonal Pd3L6 Macrotetracycles Jurček, Ondřej; Nonappa; Kalenius, Elina; Jurček, Pia; Linnanto, Juha M.; Puttreddy, Rakesh; Valkenier, Hennie; Houbenov, Nikolay; Babiak, Michal; Peterek, Miroslav; Davis, Anthony P.; Marek, Radek; Rissanen, Kari (Elsevier, 2021)Construction of structurally complex architectures using inherently chiral, asymmetric, or multi-heterotopic ligands is a major challenge in metallosupramolecular chemistry. Moreover, the hierarchical self-organization of ...
Self-assembly of metallosupramolecular rhombi from chiral concave 9,9'-spirobifluorene-derived bis(pyridine) ligands Hovorka, Rainer; Hytteballe, Sophie; Piehler, Torsten; Meyer-Eppler, Georg; Topic, Filip; Rissanen, Kari; Engeser, Marianne; Lützen, Arne (Beilstein - Institut zur Foerderung der Chemischen Wissenschaften, 2014)Two new 9,9’-spirobifluorene-based bis(4-pyridines) were synthesised in enantiopure and one also in racemic form. These ligands act as concave templates and form metallosupramolecular [(dppp)₂M₂L₂] rhombi with cis-protected ...
Influencing the self‐sorting behavior of [2.2]paracyclophane based ligands by introducing isostructural binding motifs Volbach, Lucia; Struch, Niklas; Bohle, Fabian; Topic, Filip; Schnakenburg, Gregor; Schneider, Andreas; Rissanen, Kari; Grimme, Stefan; Lützen, Arne (Wiley-VCH Verlag, 2020)Two isostructural ligands with either nitrile ( L nit ) or isonitrile ( L iso ) moieties directly connected to a [2.2]paracyclophane backbone with pseudo‐meta substitution pattern have been synthesized. The ligand itself ...
Aakeroy, Christer B.; Bryce, David L.; Desiraju, Gautam R.; Frontera, Antonio; Legon, Anthony C.; Nicotra, Francesco; Rissanen, Kari; Scheiner, Steve; Terraneo, Giancarlo; Metrangolo, Pierangelo; Resnati, Giuseppe (De Gruyter, 2019)This recommendation proposes a definition for the term “chalcogen bond”; it is recommended the term is used to designate the specific subset of inter- and intramolecular interactions formed by chalcogen atoms wherein the ...
Thiourea Organocatalysts as Emerging Chiral Pollutants : En Route to Porphyrin-Based (Chir)Optical Sensing Konrad, Nele; Horetski, Matvey; Sihtmäe, Mariliis; Truong, Khai-Nghi; Osadchuk, Irina; Burankova, Tatsiana; Kielmann, Marc; Adamson, Jasper; Kahru, Anne; Rissanen, Kari; Senge, Mathias O.; Borovkov, Victor; Aav, Riina; Kananovich, Dzmitry (MDPI AG, 2021)Environmental pollution with chiral organic compounds is an emerging problem requiring innovative sensing methods. Amino-functionalized thioureas, such as 2-(dimethylamino)cyclohexyl-(3,5-bis(trifluoromethyl)phenyl)thiourea ...