Torands revisited: Metal sequestration and self-assembly of cyclo-2,9-tris-1,10-phenanthroline hexaaza macrocycles
Schwab MG, Takase M, Mavrinsky A, Pisula W, Feng X, Gamez JA, Thiel W, Mali KS, De Feyter S, Muellen K (2015)
Publication Type: Journal article
Publication year: 2015
Journal
Book Volume: 21
Pages Range: 8426-8434
Journal Issue: 23
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.
Involved external institutions
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
Tokyo Metropolitan University (TMU) / 首都大学東京
Japan (JP)
Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen
Germany (DE)
Max-Planck-Institut für Kohlenforschung (MPI KoFo) / Max Planck Institute for Coal Research
Germany (DE)
Katholieke Universiteit Leuven (KUL) / Catholic University of Leuven
Belgium (BE)
Germany (DE)
Tokyo Metropolitan University (TMU) / 首都大学東京
Japan (JP)
Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen
Germany (DE)
Max-Planck-Institut für Kohlenforschung (MPI KoFo) / Max Planck Institute for Coal Research
Germany (DE)
Katholieke Universiteit Leuven (KUL) / Catholic University of Leuven
Belgium (BE)
How to cite
APA:
Schwab, M.G., Takase, M., Mavrinsky, A., Pisula, W., Feng, X., Gamez, J.A.,... Muellen, K. (2015). Torands revisited: Metal sequestration and self-assembly of cyclo-2,9-tris-1,10-phenanthroline hexaaza macrocycles. Chemistry - A European Journal, 21(23), 8426-8434. https://doi.org/10.1002/chem.201406602
MLA:
Schwab, Matthias Georg, et al. "Torands revisited: Metal sequestration and self-assembly of cyclo-2,9-tris-1,10-phenanthroline hexaaza macrocycles." Chemistry - A European Journal 21.23 (2015): 8426-8434.
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