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Schwab MG, Takase M, Mavrinsky A, et al. Torands Revisited: Metal Sequestration and Self-Assembly of Cyclo-2,9-tris-1,10-phenanthroline Hexaaza Macrocycles. Chemistry. 2015;21(23):8426-34doi: 10.1002/chem.201406602.
Schwab, M. G., Takase, M., Mavrinsky, A., Pisula, W., Feng, X., Gámez, J. A., Thiel, W., Mali, K. S., de Feyter, S., & Müllen, K. (2015). Torands Revisited: Metal Sequestration and Self-Assembly of Cyclo-2,9-tris-1,10-phenanthroline Hexaaza Macrocycles. Chemistry (Weinheim an der Bergstrasse, Germany), 21(23), 8426-34. https://doi.org/10.1002/chem.201406602
Schwab, Matthias Georg, et al. "Torands Revisited: Metal Sequestration and Self-Assembly of Cyclo-2,9-tris-1,10-phenanthroline Hexaaza Macrocycles." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,23 (2015): 8426-34. doi: https://doi.org/10.1002/chem.201406602
Schwab MG, Takase M, Mavrinsky A, Pisula W, Feng X, Gámez JA, Thiel W, Mali KS, de Feyter S, Müllen K. Torands Revisited: Metal Sequestration and Self-Assembly of Cyclo-2,9-tris-1,10-phenanthroline Hexaaza Macrocycles. Chemistry. 2015 Jun 01;21(23):8426-34. doi: 10.1002/chem.201406602. Epub 2015 Apr 13. PMID: 25867924.
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Chemistry. 2015 Jun 01;21(23):8426-34. doi: 10.1002/chem.201406602. Epub 2015 Apr 13.

Torands Revisited: Metal Sequestration and Self-Assembly of Cyclo-2,9-tris-1,10-phenanthroline Hexaaza Macrocycles.

Chemistry (Weinheim an der Bergstrasse, Germany)

Matthias Georg Schwab, Masayoshi Takase, Alexey Mavrinsky, Wojciech Pisula, Xinliang Feng, José A Gámez, Walter Thiel, Kunal S Mali, Steven de Feyter, Klaus Müllen

Affiliations

  1. Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz (Germany).
  2. Present Address: BASF SE, Carl-Bosch-Straße 38, 67056 Ludwigshafen (Germany).
  3. Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397 (Japan).
  4. Institute of Technical and Macromolecular Chemistry, Division of Technical Chemistry and Petrol Chemistry, RWTH Aachen University, Worringerweg 1, 52074 Aachen (Germany).
  5. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Germany).
  6. Katholieke Universiteit Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium).
  7. Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz (Germany). [email protected].

PMID: 25867924 DOI: 10.1002/chem.201406602

Abstract

A series of novel toroidal cyclo-2,9-tris-1,10-phenanthroline macrocycles with an unusual hexaaza cavity are reported. Nickel-mediated Yamamoto aryl-aryl coupling was found to be a versatile tool for the cyclotrimerization of functionalized 1,10-phenathroline precursors. Due to the now improved processability, both liquid-crystalline behavior in the bulk phase and two-dimensional self-assembly at the molecular level could be studied, for the first time, for a torand system. The macrocycles exhibited a strong affinity for the complexation of different metal cations, as evidenced by MALDI-TOF analysis and spectroscopic methods. Experimental results were correlated to an extensive computational study of the cyclo-2,9-tris-1,10-phenanthroline cavity and its binding mode for metal cations. Due to the combination of several interesting features, toroidal macrocycles may find future applications in the field of ion and charge transport through molecular channels, as well as for chemical sensing and molecular writing in surface-confined monolayers under STM conditions.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: liquid crystals; macrocycles; phenanthrolines; scanning probe microscopy; self-assembly

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