Facile synthesis of acridine-based nickel(II) complexes via metal-mediated rearrangement of diphenylamine derivative and application in H2 evolution reaction
Abstract 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 [...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2025-05-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-025-00345-3 |
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| Summary: | Abstract 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. |
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| ISSN: | 2045-2322 |