Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Structure–alkali metal cation complexation relationships for macrocyclic PNP-lariat ether ligands†

Richard A. Bartsch,*a   Eun Kyung Lee,ab   Sangki Chun,a   Nazar Elkarim,a   Krystyna Brandt,*cd   Iwona Porwolik-Czomperlik,c   Mariola Siwy,c   Dariusz Lachc  and  Jerzy Silberringe  

* Corresponding authors

a Department of Chemistry and Biochemistry, Texas Tech University, Lubbock Texas 79409-1061, USA

b Department of Chemistry, Korea University, 1-Anamdong, Seoul 136-701, South Korea

c Institute of Polymer Chemistry, Polish Academy of Sciences, 41-819 Zabrze, Poland

d Institute of Chemistry and Environmental Protection, Pedagogical University, 42-201 Czestochowa, Poland

e Faculty of Chemistry and Regional Laboratory, Jagiellonian University, 30-060 Krakow, Poland

Abstract

Water-insoluble, mono- and diarmed PNP-lariat ethers containing various aryloxy and regioisomerically-positioned binaphthylylenedioxy substituents linked to the phosphorus atoms of the cyclophosphazene ring via oxygen atoms are synthesized by regioselective, sodium ion-assisted arylolysis of tetrachloro-16-PNP-6 crown ether 1. Heterogeneously-substituted, mixed aryloxy-amino PNP-lariat ethers and bis-lariat ethers with two different substituents linked to the PNP-macrocycle via an oxygen and a nitrogen atom are prepared by stepwise arylolysis and aminolysis reactions of 1. The alkali-metal cation complexation behavior of the PNP-lariat ethers is evaluated in solvent polymeric membrane electrodes. The PNP-lariat and bis-lariat ethers exhibit pronounced selectivity for large alkali metal cations (Rb+ and Cs+) over small ones (Li+ and Na+). The selectivity is influenced by the configuration of the crown ether ring and the number of oxygen donor atoms in the ligand. For some PNP-lariat ethers, evidence for formation of 2 : 1 (ligand–metal ion) complexes with Rb+ and Cs+ is provided by ESI-MS.

Graphical abstract: Structure–alkali metal cation complexation relationships for macrocyclic PNP-lariat ether ligands

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Article information

DOI
https://doi.org/10.1039/B110415B
Article type
Paper
Submitted
14 Nov 2001
Accepted
07 Jan 2002
First published
30 Jan 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 442-448

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Structure–alkali metal cation complexation relationships for macrocyclic PNP-lariat ether ligands

R. A. Bartsch, E. K. Lee, S. Chun, N. Elkarim, K. Brandt, I. Porwolik-Czomperlik, M. Siwy, D. Lach and J. Silberring, J. Chem. Soc., Perkin Trans. 2, 2002, 442 DOI: 10.1039/B110415B

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