Synthesis, spectroscopy, and quantum-chemical calculations on 1-substituted phenyl-3,5-diphenylformazans

Tezcan, Habi̇be; Tokay, Nesrin

doi:10.1016/j.saa.2009.09.034

Cited by 22 publications

(7 citation statements)

References 19 publications

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“…59,60 Synthesis Synthesis of substituted phenylhydrazones 3a-3h. Quantum chemical calculations at the DFT Perdew, Burke and Ernzerhof (PBE) functional were done with basis sets 6-311g (2d,2p).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

2015

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In this study, formazans 5a-5h were synthesized by coupling the reactions of substituted phenylhydrazone compounds 3a-3h with diazonium salt of 4-chloro-2-phenoxybenzenamine (4). The substituted phenylhydrazones 3a-3h were obtained from the condensation of substituted phenylhydrazines 1a-1h with 4-methoxybenzaldehyde (2). The structures of the formazans were characterized by using elemental analysis, FTIR, 1 H NMR, 13 C NMR, LC-MS and the crystal structure of compound 5e was determined by X-ray crystallography. The absorption spectra of all compounds were investigated in various solvents. Although their absorption bands are only slightly dependent on the polarities of solvents, the significant change was observed by altering the electronic characteristics of the substituents. The fluorescence quantum yield properties and Stokes shifts of compounds 5a-5h in DMSO were also explored. Electrochemical properties of the new products were studied by CV measurements. In addition, computational studies were conducted at the PBE1PBE/6-311g (2d,2p) level to shed light on the structures of possible tautomers and intramolecular H-bonds.Scheme 1 Synthetic route for the formation of formazan derivatives 5a-5h.Scheme 2 Intramolecular hydrogen bonding and tautomerisation of the formazan system. View Article Onlinea Oxidation and reduction potentials from cyclic voltammograms. b Onsets of oxidation and reduction. c HOMO = À(E onset (ox) + 4.4) (eV), LUMO = À(E onset (red) + 4.4).Scheme 4 (a) Schematic representation of the structure of 5c for possible oxidation mechanisms of 5c, 5d, 5g and 5h; (b) structure of 5a for possible oxidation mechanism of 5a, 5b, 5e and 5f.

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Section: Methodsmentioning

confidence: 99%

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

2015

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“…PBE1PBE 40 method with 6-31G(d) basis set was applied because of its good performance in exploring structures and properties of formazans. 20,41,42 Analysis of the harmonic vibrational frequencies using analytical second derivatives was performed to confirm the minima. Orbital composition analysis with Mulliken partition was carried out using the Multiwfn program (a multifunctional wavefunction analyzer).…”

Section: Computationmentioning

confidence: 99%

Experimental and computational studies on the absorption properties of novel formazan derivatives

Turkoglu¹,

Çınar²

2017

Turk J Chem

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“…A number of studies have been carried out on spectral properties, crystal structures, and effects of substituents of derivatives prepared by attaching electron-withdrawing and electrondonating groups to 1,3,5-triphenylformazan [4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Spectral and electrochemical behavior of 1-[(NO2, COOH)-substituted phenyl]-3,5-diphenylformazans

2011

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1-[(NO 2 , COOH)-substituted phenyl]-3,5-diphenylformazans were synthesized. The compounds were characterized by infrared (IR), ultraviolet-visible (UV-vis), 1 H nuclear magnetic resonance (NMR), 13 C NMR spectra, elemental analysis, and cyclic voltammetry. From the UV-vis spectra of substituted formazans it was seen that k max values were shorter than the k max value of unsubstituted formazan. It was observed that the shift values were dependent on the type and position of the substituents. A correlation between Hammett substituent coefficients and k max values was obtained. The oxidation peak potentials of substituted formazans were found more anodic than that of unsubstituted formazan. The oxidation mechanism was a single step for the NO 2 -substituted formazans, and two steps for COOH-substituted formazans.

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Synthesis, spectroscopy, and quantum-chemical calculations on 1-substituted phenyl-3,5-diphenylformazans

Cited by 22 publications

References 19 publications

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

Experimental and computational studies on the absorption properties of novel formazan derivatives

Spectral and electrochemical behavior of 1-[(NO2, COOH)-substituted phenyl]-3,5-diphenylformazans

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