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<p>In this study, the formation of acridine-based metal complexes from rearrangement of diphenylamine-2,2′-dicarboxaldehyde (2,2′-dpadc) in the presence of transition metal ions was investigated. As a result, two novel isomorphic nickel(II) complexes bearing acridine-based Schiff-base ligand [NiL<sup>ACR</sup>](X)<sub>2</sub>·CH<sub>3</sub>CN (X = BF<sub>4</sub> (<b>1</b>), ClO<sub>4</sub> (<b>2</b>), L<sup>ACR</sup> = (E)-N<sup>1</sup>-(2-((acridin-4-ylmethylene)amino)ethyl)-N<sup>1</sup>-(2-aminoethyl)ethane-1,2-diamine) were successfully synthesized <i>via</i> a one-pot condensation of 2,2′-dpadc and tris(2-aminoethyl)amine (TREN) with a satisfactory yield of approximately 60%. These complexes were fully characterized by X-ray crystallography, UV-vis spectroscopy and CHN elemental analysis. Additionally, their thermal stability (thermogravimetric analysis) and electrochemical properties were also determined. A plausible mechanism for the nickel(II)-mediated rearrangement of 2,2′-dpadc to form the acridine-based nickel(II) complex was proposed. To demonstrate their potential applications, complex <b>1</b> was explored in the realm of electrocatalysis. It exhibited moderate activity towards hydrogen evolution reaction (HER). During 1-h controlled-potential electrolysis (CPE) experiments, H<sub>2</sub> production (16 micromole) was observed with faradaic efficiency of 40% when the reaction was conducted in a TBAPF<sub>6</sub>/DMF solution at -2.1&#xa0;V vs. Fc/Fc<sup>+</sup> in the presence of acetic acid as a proton source. The facile synthesis of these acridine-based nickel(II) complexes reported herein may stimulate further development of novel acridine-based ligands and their corresponding metal complexes for a wide range of applications.</p>

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Facile synthesis of acridine-based nickel(II) complexes via metal-mediated rearrangement of diphenylamine derivative and application in H2 evolution reaction

  • 期刊论文

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  • 发表日期：

    2025年5月6日

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  • Nutchanikan Phiromphu,
  • Methasit Juthathan,
  • Kittipong Chainok,
  • Chatphorn Theppitak,
  • Patchanita Thamyongkit,
  • Thawatchai Tuntulani,
  • Pannee Leeladee

摘要

In this study, the formation of acridine-based metal complexes from rearrangement of diphenylamine-2,2′-dicarboxaldehyde (2,2′-dpadc) in the presence of transition metal ions was investigated. As a result, two novel isomorphic nickel(II) complexes bearing acridine-based Schiff-base ligand [NiLACR](X)2·CH3CN (X = BF4 (1), ClO4 (2), LACR = (E)-N1-(2-((acridin-4-ylmethylene)amino)ethyl)-N1-(2-aminoethyl)ethane-1,2-diamine) were successfully synthesized via a one-pot condensation of 2,2′-dpadc and tris(2-aminoethyl)amine (TREN) with a satisfactory yield of approximately 60%. These complexes were fully characterized by X-ray crystallography, UV-vis spectroscopy and CHN elemental analysis. Additionally, their thermal stability (thermogravimetric analysis) and electrochemical properties were also determined. A plausible mechanism for the nickel(II)-mediated rearrangement of 2,2′-dpadc to form the acridine-based nickel(II) complex was proposed. To demonstrate their potential applications, complex 1 was explored in the realm of electrocatalysis. It exhibited moderate activity towards hydrogen evolution reaction (HER). During 1-h controlled-potential electrolysis (CPE) experiments, H2 production (16 micromole) was observed with faradaic efficiency of 40% when the reaction was conducted in a TBAPF6/DMF solution at -2.1 V vs. Fc/Fc+ in the presence of acetic acid as a proton source. The facile synthesis of these acridine-based nickel(II) complexes reported herein may stimulate further development of novel acridine-based ligands and their corresponding metal complexes for a wide range of applications.