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Synlett 2020; 31(14): 1384-1388
DOI: 10.1055/s-0040-1707163
DOI: 10.1055/s-0040-1707163
letter
Synthesis of a Water-Soluble, Soft N-Donor BTzBP Ligand Containing Only CHON
We gratefully acknowledge the National Science Foundation (MRI No. 1827905) for financial support to purchase a 400 MHz NMR spectrometer console and autosampler, and additional research support by the National Science Foundation: Bridges for SUCCESS (No. 0969428) and Salisbury University.Further Information
Publication History
Received: 26 May 2020
Accepted after revision: 31 May 2020
Publication Date:
24 June 2020 (online)
Abstract
A hydrophilic ligand that contains only C, H, O, and N substituents and uses a 6,6′-bis(1H-1,2,3-triazol-4-yl)-2,2′-bipyridine (BTzBP) structural core has been synthesized. The effect of adding water-soluble groups onto extractant ligands has been extensively studied to facilitate the efficient partitioning of 4f and transuranic 5f elements for the treatment of spent nuclear fuel. Soft, N-donor ligands exhibit greater binding affinities for the trivalent actinides over the trivalent lanthanides, making BTzBP ligands an ideal candidate in the search for extractants to be used on an industrial scale. To date, hydrophobic BTzBPs have been shown to exhibit physical and chemical properties that might be conducive to nuclear waste processing conditions. However, hydrophilic BTzBPs have yet to be reported. Herein, we show the synthesis of a hydrophilic BTzBP ligand featuring cationic water solubilizing groups attached to the bipyridal rings.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707163.
- Supporting Information
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- 21 Characterization Data for 8b: 1H NMR (D2O 400 MHz): δ = 2.63 (s, 6 H), 3.20 (s, 18 H), 4.00 (s, 6 H), 4.69 (s, 4 H), 8.01 (s, 2 H), 8.18 (s, 2 H). 13C NMR (100 MHz, D2O): δ = 9.2, 34.5, 52.9, 67.6, 122.8, 124.6, 134.8, 138.1, 141.8, 151.4, 155.2. IR (ATR): 669.1, 750.1, 872.9, 902.2, 934.0, 977.3, 1067.3, 1113.4, 1162.8, 1277.9, 1326.0, 1480.8, 1560.3, 1606.1, 2910, 2955, 3035, 3373 cm–1. HRMS (ESI): m/z [M]+2 calcd for C26H38N10: 245.1635; found: 245.1630.