Condensed imidazo-1,2,4-triazines. 23. Synthesis and reactions of 2-(1?-alkylhydrazino)-benzimidazole with acetyl(benzoyl)acetone

Povstyanoi, M. V.; Kruglenko, V. P.; Fedosenko, E. N.; Klyuev, N. A.

doi:10.1007/bf00480864

Cited by 5 publications

(5 citation statements)

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“…Synthesis of ligands H L 1 and H L 2 was performed under argon atmosphere. For H L 1 2‐(1‐methylhydrazinyl)‐1Hbenzo[d]imidazole [47] (64.6 mg, 0.4 mmol) and 2‐hydroxy‐5‐tritylbenzaldehyde (145.7 mg, 0.4 mmol); for H L 2 2‐(1‐methylhydrazinyl)‐1Hbenzo[d]imidazole (129.2 mg, 0.8 mmol) and 2‐hydroxy‐5‐tritylisophthalaldehyde (156.9 mg, 0.4 mmol) were transferred to two‐necked round bottom flask equipped with the reflux condenser that was previously flushed with argon. 10 mL of absolute ethanol was added via syringe and the mixture was stirred on magnetic stirrer, resulting in formation of transparent yellow solution.…”

Section: Methodsmentioning

confidence: 99%

Trityl‐Based Lanthanide‐Supramolecular Assemblies Exhibiting Slow Magnetic Relaxation

Marcinkowski

Kubicki

Patroniak

et al. 2023

Chemistry A European J

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Triphenylmethane (trityl) group has been recognized as a supramolecular synthon in crystal engineering, molecular machine rotors and stereochemical chirality inductors in materials science. Herein we demonstrate for the first time how it can be utilized in the domain of molecular magnetic materials through shaping of single molecule magnet (SMM) properties within the lanthanide complexes in tandem with other non‐covalent interactions. Trityl‐appended mono‐ (HL1) and bis‐compartmental (HL2) hydrazone ligands were synthesized and complexated with Dy(III) and Er(III) triflate and nitrate salts to generate four monometallic (1‐4) and two bimetallic (5, 6) complexes. The static and dynamic magnetic properties of 1–6 were investigated, revealing that only ligand HL1 induces assemblies (1‐4) capable of showing SMM behaviour, with Dy(III) congeners (1, 2) able to exhibit the phenomenon also under zero field conditions. Theoretical ab initio studies helped in determination of Dy(III) energetic levels, magnetic anisotropic axes and corroborated magnetic relaxation mechanisms to be a combination of Raman and quantum tunnelling in zero dc field, the latter being cancelled in the optimum non‐zero dc field. Our work represents the first study of magneto‐structural correlations within the trityl Ln‐SMMs, leading to generation of slowly relaxing zero‐field dysprosium complexes within the hydrogen bonded assemblies.

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Section: Methodsmentioning

confidence: 99%

Trityl‐Based Lanthanide‐Supramolecular Assemblies Exhibiting Slow Magnetic Relaxation

Marcinkowski

Kubicki

Patroniak

et al. 2023

Chemistry A European J

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“…Subcomponent self-assembly 23,28 of hydrated Ln(NO 3 ) 3 salt with 2-(methylhydrazino)benzimidazole and 4-tert-butyl-2,6diformylphenol in 2:6:3 molar ratio in the presence of triethylamine leads to isolation of yellow crystals of the following formula: [Ln 2 L 3 ](NO 3 ) 3 where Ln -Tb (1), Dy(2), Ho (3), Er(4), Tm (5), Yb(6) (Figure 1). X-Ray crystal data of 4 is shown as a representative one, since all compounds were found to be isostructural -which is notable taking into consideration the lanthanide contraction.…”

Section: Crystal Structuresmentioning

confidence: 99%

“…All lanthanide complexes were synthesized in a one-pot template reaction from 2-(1-methylhydrazinyl)-1H-benzo [d]imidazole (synthesized via a slightly modified procedure adapted from Povstyanoi et al, yield: 90%), 23 4-tert-butyl-2,6-diformylphenol and Ln(NO 3 ) 3 •xH 2 O (where Ln can be Tb, Dy, Ho, Er, Tm, or Yb and x can be 5 or 6). To a 50 ml round bottom flask containing hydrazine derivative (53.3 mg, 0.33 mmol) and dialdehyde (33.9 mg, 0.16 mmol) dissolved in 10 ml of MeOH abs , hydrated Ln(III) salt (0.11 mmol) and another 10 ml of MeOH abs were added which resulted in the formation of a clear yellow solution.…”

Section: Synthesis Of Complexesmentioning

confidence: 99%

“…Subcomponent self-assembly 23,28 of hydrated Ln(NO 3 ) 3 salt with 2-(methylhydrazino)benzimidazole A and 4-tert-butyl-2,6diformylphenol B in 2 : 6 : 3 molar ratio in the presence of triethylamine leads to isolation of yellow crystals of the following formula: [Ln 2 L 3 ](NO 3 ) 3 where Ln can be Tb(1), Dy(2), Ho(3), Er(4), Tm(5), or Yb(6) (Fig. 1).…”

Section: Crystal Structuresmentioning

confidence: 99%

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The first example of erbium triple-stranded helicates displaying SMM behaviour

et al. 2015

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A series of isostructural C3-symmetrical triple stranded dinuclear lanthanide [Ln2L3](NO3)3 molecules have been synthesized using subcomponent self-assembly of Ln(NO3)3 with 2-(methylhydrazino)benzimidazole and 4-tert-butyl-2,6-diformylphenol, where Ln = Tb (1), Dy (2), Ho (3), Er (4), Tm (5), and Yb (6). The temperature dependent and field dependent magnetic properties of 1-6 were modeled using the van Vleck approximation including the crystal field term HCF, the super-exchange term HSE and the Zeeman term HZE. Ferromagnetic interactions were found in 1, 2, 4 and 6, while antiferromagnetic interactions were found in 3 and 5. The erbium analogue reveals field induced SMM behaviour.

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“…The aldehyde A and the benzimidazole derivative B have been obtained according to a previously reported procedures [20,26,27]. NMR spectra were recorded on a Bruker UltraShield 300 MHz spectrometer (Bruker Corporation, Billerica, MA, USA) and were calibrated against the residual protonated solvent signal (d 6 -DMSO, δ 2.50 ppm).…”

Section: Generalmentioning

confidence: 99%

Reductive Electropolymerization and Electrochromism of Iron(II) Complex with Styrene-Based Ligand

et al. 2021

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The benzimidazole-based ligand containing polymerizable styrene group has been prepared via condensation of picolinaldehyde derivative containing styrene moiety and benzimidazole-based hydrazine. The ligand reacted with iron(II) tetrafluoroborate and iron(II) trifluoromethanesulfonate giving red-brown complexes of Fe(II) ions of formula [FeL2]X2, where X = CF3SO3− (1) or BF4− (2). Reductive electropolymerization was used to obtain a thin layer of the polymeric complex, poly-1. Further investigation of electrochemical properties of the compound by cyclic voltammetry showed two quasi-reversible redox processes assigned to electrooxidation and electroreduction of the polymer. Spectroelectrochemical measurements confirmed that the polymer undergoes the color changes during oxidation and reduction process. The polymer in its neutral state (Fe(II)) is yellow and it exhibits absorption band at 370 nm, after oxidation to Fe(III) state absorption band shifts to 350 nm and the polymer is almost colorless. While the metal ions are reduced to Fe(I) absorption band at around 410 nm has been observed and the polymer changed its color to intense yellow. The stability of the polymer during multiple oxidation/reduction cycles has also been investigated.

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Condensed imidazo-1,2,4-triazines. 23. Synthesis and reactions of 2-(1?-alkylhydrazino)-benzimidazole with acetyl(benzoyl)acetone

Cited by 5 publications

References 1 publication

Trityl‐Based Lanthanide‐Supramolecular Assemblies Exhibiting Slow Magnetic Relaxation

Trityl‐Based Lanthanide‐Supramolecular Assemblies Exhibiting Slow Magnetic Relaxation

The first example of erbium triple-stranded helicates displaying SMM behaviour

Reductive Electropolymerization and Electrochromism of Iron(II) Complex with Styrene-Based Ligand

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