Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes

Salih Ilhan; Hamdi Temel; Ismail Yilmaz; Memet Sekerci

doi:10.1016/j.jorganchem.2007.05.031

Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes

Salih Ilhan^*, Hamdi Temel, Ismail Yilmaz, Memet Sekerci

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

80 Citations (Scopus)

Abstract

A new macrocyclic ligand, 1,3,5-triaza-2,4:7,8:13,14-tribenzo-9,12-dioksa-cyclopentadeca-1,5-diene was synthesized by reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane. Then, its Cu(II), Ni(II), Pb(II), Co(III) and La(III) complexes were synthesized by the template effect by the reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane and Cu(NO₃)₂ · 3H₂O, Ni(NO₃)₂ · 6H₂O, Pb(NO₃)₂, Co(NO₃)₂ · 6H₂O, La(NO₃)₃ · 6H₂O, respectively. The ligand and its metal complexes have been characterized by elemental analysis, IR, ¹H and ¹³C NMR, UV-Vis spectra, magnetic susceptibility, thermal gravimetric analysis, conductivity measurements, mass spectra, and cyclic voltammetry. All complexes are diamagnetic and Cu(II) complex is binuclear. The Co(II) was oxidized to Co(III). The comparative electrochemical studies show that the nickel complex exhibited a quasi-reversible one-electron reduction process, while copper and cobalt complexes gave irreversible reduction processes in DMSO solution.

Original language	English
Pages (from-to)	3855-3865
Number of pages	11
Journal	Journal of Organometallic Chemistry
Volume	692
Issue number	18
DOIs	https://doi.org/10.1016/j.jorganchem.2007.05.031
Publication status	Published - 15 Aug 2007

Funding

We are grateful to Dicle University Research Found (DUAPK-03-EF-24) for the support of this research.

Funders	Funder number
Dicle University Research Found	DUAPK-03-EF-24

Keywords

2,6-Diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane
Macrocyclic Schiff base
Macrocyclic Schiff base complexes

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10.1016/j.jorganchem.2007.05.031

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title = "Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes",

abstract = "A new macrocyclic ligand, 1,3,5-triaza-2,4:7,8:13,14-tribenzo-9,12-dioksa-cyclopentadeca-1,5-diene was synthesized by reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane. Then, its Cu(II), Ni(II), Pb(II), Co(III) and La(III) complexes were synthesized by the template effect by the reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane and Cu(NO3)2 · 3H2O, Ni(NO3)2 · 6H2O, Pb(NO3)2, Co(NO3)2 · 6H2O, La(NO3)3 · 6H2O, respectively. The ligand and its metal complexes have been characterized by elemental analysis, IR, 1H and 13C NMR, UV-Vis spectra, magnetic susceptibility, thermal gravimetric analysis, conductivity measurements, mass spectra, and cyclic voltammetry. All complexes are diamagnetic and Cu(II) complex is binuclear. The Co(II) was oxidized to Co(III). The comparative electrochemical studies show that the nickel complex exhibited a quasi-reversible one-electron reduction process, while copper and cobalt complexes gave irreversible reduction processes in DMSO solution.",

keywords = "2,6-Diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane, Macrocyclic Schiff base, Macrocyclic Schiff base complexes",

author = "Salih Ilhan and Hamdi Temel and Ismail Yilmaz and Memet Sekerci",

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TY - JOUR

T1 - Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes

AU - Ilhan, Salih

AU - Temel, Hamdi

AU - Yilmaz, Ismail

AU - Sekerci, Memet

PY - 2007/8/15

Y1 - 2007/8/15

N2 - A new macrocyclic ligand, 1,3,5-triaza-2,4:7,8:13,14-tribenzo-9,12-dioksa-cyclopentadeca-1,5-diene was synthesized by reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane. Then, its Cu(II), Ni(II), Pb(II), Co(III) and La(III) complexes were synthesized by the template effect by the reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane and Cu(NO3)2 · 3H2O, Ni(NO3)2 · 6H2O, Pb(NO3)2, Co(NO3)2 · 6H2O, La(NO3)3 · 6H2O, respectively. The ligand and its metal complexes have been characterized by elemental analysis, IR, 1H and 13C NMR, UV-Vis spectra, magnetic susceptibility, thermal gravimetric analysis, conductivity measurements, mass spectra, and cyclic voltammetry. All complexes are diamagnetic and Cu(II) complex is binuclear. The Co(II) was oxidized to Co(III). The comparative electrochemical studies show that the nickel complex exhibited a quasi-reversible one-electron reduction process, while copper and cobalt complexes gave irreversible reduction processes in DMSO solution.

AB - A new macrocyclic ligand, 1,3,5-triaza-2,4:7,8:13,14-tribenzo-9,12-dioksa-cyclopentadeca-1,5-diene was synthesized by reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane. Then, its Cu(II), Ni(II), Pb(II), Co(III) and La(III) complexes were synthesized by the template effect by the reaction of 2,6-diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane and Cu(NO3)2 · 3H2O, Ni(NO3)2 · 6H2O, Pb(NO3)2, Co(NO3)2 · 6H2O, La(NO3)3 · 6H2O, respectively. The ligand and its metal complexes have been characterized by elemental analysis, IR, 1H and 13C NMR, UV-Vis spectra, magnetic susceptibility, thermal gravimetric analysis, conductivity measurements, mass spectra, and cyclic voltammetry. All complexes are diamagnetic and Cu(II) complex is binuclear. The Co(II) was oxidized to Co(III). The comparative electrochemical studies show that the nickel complex exhibited a quasi-reversible one-electron reduction process, while copper and cobalt complexes gave irreversible reduction processes in DMSO solution.

KW - 2,6-Diaminopyridine and 1,2-bis(2-carboxyaldehyde phenoxy)ethane

KW - Macrocyclic Schiff base

KW - Macrocyclic Schiff base complexes

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DO - 10.1016/j.jorganchem.2007.05.031

M3 - Article

AN - SCOPUS:34547121745

SN - 0022-328X

VL - 692

SP - 3855

EP - 3865

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 18

ER -

Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes

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