Bis(hydroxyamino)triazines: versatile and high-affinity tridentate hydroxylamine ligands for selective iron(III) chelation

Dalton Transactions : an International Journal of Inorganic Chemistry
Irina EkeltchikArtem Melman

Abstract

A new versatile family of chelating agents based on bis(hydroxyamino)-1,3,5-triazines, BHTs, is described. The properties of different BHT ligands are determined by electrochemistry, spectroscopy and titrimetry revealing high redox stability, transparency in the visible range, and diprotic acid-like behaviour in the 5-9 pH range. The iron(III) and iron(II)-BHT complexes were studied revealing high affinity of BHTs to iron(III). Electrochemical studies show exceptional preference of the BHT ligands to iron(III) over iron(II), this, in addition to their small size and their fast and reversible electrochemistry makes them potentially useful electrochemical redox couples for the low end of the aqueous potential window (<0.6 V, vs. NHE). The synthetic versatility of the new ligands allows easy tuning of the hydrophobicity, redox potential, and to some extent the stability constant of the complexes by alteration of the peripheral groups appended to the BHTs.

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Citations

Aug 23, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Dani PeriArtem Melman
Aug 25, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Vladimiros A NikolakisThemistoklis A Kabanos
Apr 1, 2011·Expert Opinion on Therapeutic Patents·Hossein HeliKhashayar Karimian
Dec 17, 2009·Bioorganic & Medicinal Chemistry Letters·Daekyu SunArtem Melman
Mar 25, 2009·Chembiochem : a European Journal of Chemical Biology·Jian ZhouEvgeny Katz
Nov 10, 2010·Chemical Communications : Chem Comm·Fadi Bou-AbdallahArtem Melman
Feb 20, 2019·Nature Communications·Alexander S IvanovIlja Popovs
Aug 27, 2009·Inorganic Chemistry·Galina MelmanArtem Melman

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