Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions

Valizadeh, Hassan; Shomali, Ashkan; Ghorbani, Jalal; Noorshargh, Saeideh

doi:10.1016/j.dyepig.2015.02.007

Cited by 10 publications

(6 citation statements)

References 21 publications

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“…In recent years, several methods have been reported for the synthesis of aromatic azo components [ 8 , 57 , 58 , 59 , 60 ]. Although remarkable developments have been achieved in this field still the most important method for the preparation of these classes of compounds is the diazotization-azo coupling reaction.…”

Section: Resultsmentioning

confidence: 99%

Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes

Skotnicka

Czeleń

2021

Materials

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Novel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. 1H, 11B, 13C, 15N, and 19F nuclear magnetic resonance (NMR) spectra of substituted 1-phenylazonaphthalen-2-ol difluoroboranes and their parent azo dyes were recorded and discussed. The absorption and emission properties of synthesized compounds were investigated in solvents of varying polarity. They were found to be fluorescent despite the presence of the azo group. The azo group rotation was blocked by complexing with -BF2 to get a red shift in absorption. Solvent-dependent spectral properties of compounds were investigated using Lipper-Mataga and Bakhshiev plot. The calculated DFT energies and Frontier Molecular Orbitals calculations of the studied compounds were proved to be consistent with the experimental observations.

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Section: Resultsmentioning

confidence: 99%

Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes

Skotnicka

Czeleń

2021

Materials

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“…However, other specific methods include metal-catalyzed coupling [22][23][24], the oxidation of aromatic amines [25,26], reductive coupling of nitro aromatic compounds [26,27], conversion and reduction of aromatic N-oxides [28][29][30], catalytic coupling and thermal decomposition of aromatic azide compounds [31,32], and the catalytic coupling of aromatic diazonium salts [33][34][35][36]. However, these methods do not meet the requirements of green chemistry owing to the organic solvent and heavy metal ions in the reducing agent or antioxidant.…”

Section: Introductionmentioning

confidence: 99%

New Insight into the Synthesis of Aromatic Azo Compounds Assisted by Surface Plasmon Resonance

Wang

Song

et al. 2016

Plasmonics

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The application of surface plasmon resonance (SPR)-assisted catalysis to synthesize aromatic azo compounds was first reported in 2010. The feasibility of SPRassisted catalytic decomposition of aromatic azo compounds has also been confirmed, both experimentally and theoretically. Compared with traditional chemical synthesis methods, SPR-assisted catalysis has many advantages, such as high efficiency, low energy consumption, and high selectivity. The synthetic route to aromatic azo compounds and the kinetics thereof can be efficiently monitored by Raman spectroscopy. In this way, it has been confirmed that SPR-assisted catalysis occurs on the surface of noble metal nanoparticles (NPs). Mechanistically, the process involves transfer of electrons excited by the incident laser from noble metal NPs to 3 O 2 in air to form 2 O 2 − for the generation of SPR on the surface of the noble metal nanoparticles. The 2 O 2 − can then react with the metal to form metal oxides or hydroxides, which in turn can react with the substrate molecule. The substrate molecule can gain a proton from a proton donor or lose a proton to form a radical, which can react further. This mechanism accounts for the conversion of 4-aminothiophenol (PATP) into 4, 4-dimercaptoazobenzene (DMAB). The metal oxide or hydroxide formed reacts with PATP in an acid-base neutralization process. PATP radicals (PATP · ) are formed by the loss of a proton, and pairing of two PATP · leads to the intermediate product DMHAB. Deprotonation DMHAB then gives the final product DMAB.

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“…6,7 However, the yield is low, and the toxic and harmful reagent of nitrous acid is used, unfriendly to the environment. 8,9 Recently, aromatic azo compounds have also been synthesized via plasmon-mediated reduction of nitroaromatic compounds at high efficiency 10−14 because of the high absorption coefficient and utilization efficiency of light in plasmonic nanostructures. 15−19 However, the potential of plasmonic nanostructures in chemical reactions is still not fully explored due to the limited lifetime of the plasmongenerated hot carriers.…”

Section: ■ Introductionmentioning

confidence: 99%

“…As important chemical reagents, aromatic azo compounds are widely used in industrial production of dyes, food additives, drugs, free radical initiators, and optical electronic components. − Traditionally, aromatic azo compounds are synthesized via transition-metal-catalyzed oxidation of aromatic amines. , However, the yield is low, and the toxic and harmful reagent of nitrous acid is used, unfriendly to the environment. , Recently, aromatic azo compounds have also been synthesized via plasmon-mediated reduction of nitroaromatic compounds at high efficiency − because of the high absorption coefficient and utilization efficiency of light in plasmonic nanostructures. − However, the potential of plasmonic nanostructures in chemical reactions is still not fully explored due to the limited lifetime of the plasmon-generated hot carriers. − It is necessary to develop new strategies to further enhance the rate and efficiency of the coupling reaction of nitroaromatic compounds.…”

Section: Introductionmentioning

confidence: 99%

Molecular Cocatalyst-Induced Enhancement of the Plasmon-Mediated Coupling of p-Nitrothiophenols at the Silver Nanoparticle–Graphene Oxide Interface

Guan

Zhu

Yue

et al. 2021

ACS Appl. Nano Mater.

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The plasmon-mediated coupling reaction of nitroaromatic compounds is an effective strategy to synthesize the aromatic azo compounds that are widely applied in material science, pharmacy, and agricultural chemistry. Nonetheless, the reaction rate can be further improved since the lifetime of the plasmon-generated hot carriers is limited to femtoseconds or picoseconds. Herein, using in situ plasmon-enhanced Raman spectroscopy, we reveal that the adsorbed positively charged methyl violet molecules on the silver nanoparticle (Ag NP)− graphene oxide (GO) composite structure act as simple and costeffective molecular cocatalysts, largely boosting the coupling of pnitrothiophenol to p,p′-dimercaptoazobenzene. This boosting is attributed to the promoted separation of the plasmon-generated hot carriers at the Ag NP−GO interface. In addition, the reduction of laser power will help to promote the efficiency of the MVinduced acceleration. This work provides a highly simple, efficient, and cost-effective strategy to accelerate the coupling reaction of nitroaromatic compounds, and this strategy can be extended to the acceleration of many other plasmon-mediated chemical reactions.

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Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions

Cited by 10 publications

References 21 publications

Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes

Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes

New Insight into the Synthesis of Aromatic Azo Compounds Assisted by Surface Plasmon Resonance

Molecular Cocatalyst-Induced Enhancement of the Plasmon-Mediated Coupling of p-Nitrothiophenols at the Silver Nanoparticle–Graphene Oxide Interface

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