The synthesis characterization of historical novel azo pigments: implications for conservation science

Lomax, Suzanne Quillen; Lomax, Joseph F.

doi:10.1186/s40494-019-0343-1

Cited by 11 publications

(9 citation statements)

References 10 publications

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“…Specifically, both the spectra display a characteristic doublet of peaks at 257 and 282 cm À1 , while other peaks at 395, 472, 511, 550, 638, 712, and 1087 cm À1 are also observable in both spectra. 68,77 At higher wavenumbers, differences between the spectra of the two dyes were evident despite both still maintaining similar spectral patterns. The Raman spectrum of Arancio Luce G has an intense peak at 1235 cm À1 ; in the spectrum for Giallo Italana 2G, this signal is weaker and shifted to 1228 cm À1 .…”

Section: Resultsmentioning

confidence: 99%

The 20th century and its new colours: Investigating the molecular structures of historical synthetic dyes using Raman spectroscopy

Ciccola,

McClure,

Serafini

et al. 2023

J Raman Spectroscopy

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Characterising synthetic dyes on heritage textiles represents a relatively recent research frontier, which aims to obtain new information about the evolution of textile manufacturing and industrial chemistry. Whilst spectral enhancement or amplification methods are often considered a requirement for the Raman analysis of textile dyes, this work highlights the potential of standard Raman spectroscopy for the non‐invasive analysis of synthetically dyed fibres. In this research, Raman spectroscopy was used for the chemical characterisation of early 20th century synthetic dyes, in both powder form and on dyed fibres. The dyes were produced by the Italian company Azienda Coloranti Nazionali e Affini (ACNA) and housed in the Sapienza University Museum of Chemistry. The investigation first employed literature research into the ACNA's commercial nomenclature. This information was used to hypothesise likely molecular structures of the dyes, pointing towards the azo dye class. The application of Raman spectroscopy confirmed these hypotheses and the high‐quality spectra collected provided structural information about the dye molecules. Spectral features of azo‐groups, aromatic moieties, and substituents were observable in spectra. Comparison with a Raman spectrum of wool allowed confident dye signal attribution, and some spectra displayed features linked to changes in the fibre during the dyeing process. Combining literature research and Raman vibrational information proved a powerful non‐invasive approach for the characterisation of synthetic dyes, allowing molecular identification of some colorants and structural information for most. Standard Raman spectroscopy may provide a widely applicable, non‐invasive method for acquiring information about synthetically dyed historical and artistic textiles in future research.

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Section: Resultsmentioning

confidence: 99%

The 20th century and its new colours: Investigating the molecular structures of historical synthetic dyes using Raman spectroscopy

Ciccola,

McClure,

Serafini

et al. 2023

J Raman Spectroscopy

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“…Schiff bases prepared from condensation of aromatic amines with aromatic aldehydes are more stable due to the occurrence of resonance phenomenon [10]. In homocyclic and heterocyclic forms, azo compounds (-N=N-) play a fundamental role in the dye and pigment industries [11,12]. It extensively entered the analytical chemistry fields [13,14], actually into the industrialization of drugs and other medications [15], and LCD color filters [16].…”

Section: Introductionmentioning

confidence: 99%

Untitled

2023

J. Med. Chem. Sci.

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Three of new azo-Schiff base ligands were prepared in this work via the preparation of Schiff base ((E)-2-(((2,5-dichlorophenyl)imino)methyl)phenol DCSS) produced from the condensation reaction between salicyaldehyde and (2,5-dichloroaniline), this Schiff base was regarded as a coupling component in azo reactions to form the new azo-Schiff ligands, respectively, via the reaction of the diazonium salts of the (2,5difluoroaniline, 4-chloro-2-fluoroaniline and 4-bromo-2-fluoroaniline) with the previous Schiff base (DCSS). These new Azo-Schiff ligands were characterized with many spectroscopic techniques such as (FT-IR, 1 H-NMR, Mass spectra, UV-Visible, and elementary analysis) to ensure their preparation. Five divalent transition ions (Co, Ni, Cu, Pd, and Pt) complexes were prepared for each ligand and characterized (some of them) with the previous techniques, the mole ratio of the cobalt and copper complexes was (1:2), while the rest (Ni, Pd, and Pt) complexes have a (1:1) ratios. In addition, complementary techniques, such as atomic absorption, molar electrical conductivity, and magnetic susceptibility were performed to deduce their geometries and form the collected data. The square planer geometry was examined. The biological study includes the antibacterial screening against two types of bacterial species gram-negative (E.coli) and gram-positive (S. aureus) using tetracycline as a reference antibiotic. Antioxidant assay of some of the prepared ligands and their complexes as well as an MC7 cell line breast cancer assay for two prepared complexes (PdL1 and PtL2) and as compared, they noticed that the platinum azo-Schiff complex has an IC50 = 56.78 a more active anticancer function than the palladium complex with IC50 = 74.64.

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“…The reaction conditions may act as catalysts, corrosion inhibitors, and intermediates in organic synthesis [9][10][11][12]. In homocyclic and heterocyclic forms, azo compounds (-N=N-) play an essential role in the dye and pigment industries [13][14][15][16]. They have extensively entered the analytical chemistry fields [17,18], indeed into the manufacturing of drugs and other medications [19], and LCD color filters [20].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of New (Halogenated Azo-Schiff) Ligands with Some of their Transition Metal Ions Complexes

Kadhim

Mahdi

2022

eijs

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Two new halogenated azo-Schiff ligands were prepared in two steps. The first step included a condensation between 4-amino acetophenone and 2-fluoro-4-bromo aniline to give the corresponding Schiff base. In the second step, the diazonium salt of this Schiff base reacted with 2-naphthol and 4,5-diphenylimidazole to form two new azo-Schiff base derivatives as ligands; (3-((E)-(4-((E)-1-((4-bromo-2-fluorophenyl) imino)ethyl) phenyl) diazenyl) naphthalen-2-ol (HSBAN) (L1) and ((E)-N-(4-bromo-2-fluorophenyl)-1-(4-((E)-(4,5-diphenyl-1H-imidazol-2-yl)diazenyl) phenyl) ethan-1-imine) (HSBAI) (L2), respectively. These new ligands were characterized by mass spectrometry, FT-IR, 1H NMR, UV-Visible spectroscopy and elemental microanalysis (CHN). Five divalent transition metal ion complexes (Co, Ni, Cu, Cd, and Hg) were prepared and characterized, beyond the determination of the optimal condition (concentration, pH value, and the mole ratio M:L) using UV-visible studies. Additionally, complementary techniques, such as atomic absorption, electrical conductivity and magnetic susceptibility, were performed to deduce their geometries. The comprehensive study suggested an octahedral geometry for all complexes except Cd and Hg complexes of the first ligand.

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The synthesis characterization of historical novel azo pigments: implications for conservation science

Cited by 11 publications

References 10 publications

The 20th century and its new colours: Investigating the molecular structures of historical synthetic dyes using Raman spectroscopy

The 20th century and its new colours: Investigating the molecular structures of historical synthetic dyes using Raman spectroscopy

Untitled

Preparation and Characterization of New (Halogenated Azo-Schiff) Ligands with Some of their Transition Metal Ions Complexes

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