A novel synthesis of 2,3-diaminophenazine

Luo, Mingbiao; Tai, Liu; Tao, Feng; Sun, Jing; Li, Rong

doi:10.1007/s11164-011-0366-z

Cited by 11 publications

(7 citation statements)

References 5 publications

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“…Hydrogen bonding (Scheme ) and van der Waals interactions play an important role in balancing repulsion and π–π interactions . Besides this, the water molecules can be connected through hydrogen bonding with each other and with the pyrazine N atoms situated in the middle of the molecule . Due to these complex directionally driven interactions, micro‐ and macro‐rods are formed.…”

Section: Resultsmentioning

confidence: 99%

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Self-assembled centimetre-sized rods obtained in the oxidation of o -phenylenediamine and aniline

et al. 2015

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Morphologically well-defined rods approximately one centimetre in length are effectively and economically obtained by mixing ortho-phenylenediamine oPD (30mM) with ammonium persulfate (APS) (12.5 mM) in an acidic solution (0.37 M HCl) at room temperature with and without the presence of 50 mM aniline. These, self-assembled, morphologically uniform products can be potentially scaled-up and used as morphological templates to fabricate well-defined structures of other materials such as conducting polymers.The products were characterized by Raman, UV-Vis, high-resolution NMR ( 1 H and 13 C), XRD, scanning electron microscopy (SEM), MS (mass spectrometry) and elemental analysis.Apart from certain differences in a visual appearance and in XRD diffractograms, other analytical data suggest that there were no structural changes upon addition of aniline into a reaction mixture. NMR and MS spectra imply that all syntheses carried out either with or without aniline resulted in a mixture of two products, attributed to 2,3-phenazinediamine and 3-aminophenazin-2-ol. A formation mechanism based on hydrogen bonding and π-π stacking has been proposed.

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Section: Resultsmentioning

confidence: 99%

“…2 Besides this, the water molecules can be connected through hydrogen bonding with each other and with the pyrazine N atoms situated in the middle of the molecule. 32 Due to these complex directionally driven interactions, micro-and macro-rods are formed.…”

Section: Formation Mechanismmentioning

confidence: 99%

Self-assembled centimetre-sized rods obtained in the oxidation of o -phenylenediamine and aniline

et al. 2015

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“… At pHs from 4 to 6, a transition at around pH = 5 occurs in agreement with DAPH + pK a = 5.1 [ 31 , 41 ]. At pHs from 2 to 3, the dominant DAP form is DAPH + , with ring nitrogen being protonated as evidenced by XRD [ 52 , 53 ] instead of the NH 2 group as proposed by Brown and coauthors [ 41 ]. The SERS spectrum of DAPH + corresponds well with the normal Raman spectrum of crystalline DAP×HCl [ 31 ].…”

Section: Figure A1mentioning

confidence: 99%

Highly Sensitive Measurement of Horseradish Peroxidase Using Surface-Enhanced Raman Scattering of 2,3-Diaminophenazine

Evtushenko,

Gavrilina,

Vasilyeva

et al. 2024

Molecules

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The development of various enzyme-linked immunosorbent assays (ELISAs) coupled with surface-enhanced Raman scattering (SERS) detection is a growing area in analytical chemistry due to their potentially high sensitivity. A SERS-based ELISA with horseradish peroxidase (HRP) as an enzymatic label, an o-phenylenediamine (oPD) substrate, and a 2,3-diaminophenazine (DAP) enzymatic product was one of the first examples of such a system. However, the full capabilities of this long-known approach have yet to be revealed. The current study addresses a previously unrecognized problem of SERS detection stage performance. Using silver nanoparticles and model mixtures of oPD and DAP, the effects of the pH, the concentration of the aggregating agent, and the particle surface chloride stabilizer were extensively evaluated. At the optimal mildly acidic pH of 3, a 0.93 to 1 M citrate buffer, and AgNPs stabilized with 20 mM chloride, a two orders of magnitude advantage in the limits of detection (LODs) for SERS compared to colorimetry was demonstrated for both DAP and HRP. The resulting LOD for HRP of 0.067 pmol/L (1.3 amol per assay) underscores that the developed approach is a highly sensitive technique. We suppose that this improved detection system could become a useful tool for the development of SERS-based ELISA protocols.

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“…The aromatic primary amines (5 g) was partially dissolved in conc. HCl (5 mL) in 80 mL water and cooled to 0-5°C [34]. The solution of NaNO 2 (2 g) in 5 mL water was added slowly to the reaction mixture, and the reaction temperature was kept below 5°C.…”

Section: Experimental Sections 31 General Experimental Procedures Of mentioning

confidence: 99%

Synthesis and Optical Properties of Near-Infrared (NIR) Absorbing Azo Dyes

Patil¹,

Chaudhary²

2020

Chemistry and Technology of Natural and Synthetic Dyes and Pigments

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This chapter provides a general overview and information on near-infrared (NIR) absorbing azo dyes. In this work, we have developed an efficient and simple protocol for the synthesis of novel A-π-D-π-A NIR azo dyes. The near-infrared absorbing azo dyes were synthesized by using 2-hydroxy-1,4 naphthoquinone (Lawsone) and different substituted aromatic primary amines. Furthermore, author developed push-pull chromophores of A-π-D-π-A type containing an electron-withdrawing azo core, phenazine moieties, and a hydroxyl group as electron donor. The benzo[a]quinoxalino[2,3-i]phenazin-5-ol moiety was introduced to make the system planer as well as to increase the π-conjugation. The optical properties of these dyes were studied in N,N-dimethylformamide (DMF).

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A novel synthesis of 2,3-diaminophenazine

Abstract: The title heterocyclic 2,3-diaminophenazine (DAP) hydrochloride with the crystallization solvent were obtained from three different routes and their structures were determined by X-ray diffraction, elemental analysis, and IR.

Cited by 11 publications

References 5 publications

Self-assembled centimetre-sized rods obtained in the oxidation of o -phenylenediamine and aniline

Self-assembled centimetre-sized rods obtained in the oxidation of o -phenylenediamine and aniline

Highly Sensitive Measurement of Horseradish Peroxidase Using Surface-Enhanced Raman Scattering of 2,3-Diaminophenazine

Synthesis and Optical Properties of Near-Infrared (NIR) Absorbing Azo Dyes

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