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Lee S, Hirsch BE, Liu Y, et al. Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers. Chemistry. 2015;22(2):560-9doi: 10.1002/chem.201503161.
Lee, S., Hirsch, B. E., Liu, Y., Dobscha, J. R., Burke, D. W., Tait, S. L., & Flood, A. H. (2016). Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers. Chemistry (Weinheim an der Bergstrasse, Germany), 22(2), 560-9. https://doi.org/10.1002/chem.201503161
Lee, Semin, et al. "Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,2 (2016): 560-9. doi: https://doi.org/10.1002/chem.201503161
Lee S, Hirsch BE, Liu Y, Dobscha JR, Burke DW, Tait SL, Flood AH. Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers. Chemistry. 2016 Jan 11;22(2):560-9. doi: 10.1002/chem.201503161. Epub 2015 Nov 23. PMID: 26593327.
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Chemistry. 2016 Jan 11;22(2):560-9. doi: 10.1002/chem.201503161. Epub 2015 Nov 23.

Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers.

Chemistry (Weinheim an der Bergstrasse, Germany)

Semin Lee, Brandon E Hirsch, Yun Liu, James R Dobscha, David W Burke, Steven L Tait, Amar H Flood

Affiliations

  1. Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN 47405 (USA).
  2. Current Address: Beckman Institute for Advanced Science and Technology, University of Illinois at Urbana-Champaign, 405 N Mathews Ave, Urbana, IL 61801 (USA).

PMID: 26593327 DOI: 10.1002/chem.201503161

Abstract

Programming the synthesis and self-assembly of molecules is a compelling strategy for the bottom-up fabrication of ordered materials. To this end, shape-persistent macrocycles were designed with alternating carbazoles and triazoles to program a one-pot synthesis and to bind large anions. The macrocycles bind anions that were once considered too weak to be coordinated, such as PF6 (-) , with surprisingly high affinities (β2 =10(11)  M(-2) in 80:20 chloroform/methanol) and positive cooperativity, α=(4 K2 /K1 )=1200. We also discovered that the macrocycles assemble into ultrathin films of hierarchically ordered tubes on graphite surfaces. The remarkable surface-templated self-assembly properties, as was observed by using scanning tunneling microscopy, are attributed to the complementary pairing of alternating triazoles and carbazoles inscribed into both the co-facial and edge-sharing seams that exist between shape-persistent macrocycles. The multilayer assembly is also consistent with the high degree of molecular self-association observed in solution, with self-association constants of K=300 000 M(-1) (chloroform/methanol 80:20). Scanning tunneling microscopy data also showed that surface assemblies readily sequester iodide anions from solution, modulating their assembly. This multifunctional macrocycle provides a foundation for materials composed of hierarchically organized and nanotubular self-assemblies.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: crystal engineering; nanostructures; nanotubes; self-assembly; supramolecular chemistry; surface chemistry

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