2872-52-8

Usage

Chemical Properties

Dark red powder

Uses

Different sources of media describe the Uses of 2872-52-8 differently. You can refer to the following data:
1. Disperse orange 3 is used as a dye in nylon and polyester; stocking dye.
2. Disperse Red 1 is an azo disperse dye which is water insoluble. Disperse Red 1 can be used to dye polyester and acetate fibers. Dyes and metabolites, Environmental Testing.

Preparation

4-Nitrobenzenamine diazo, and N-ethyl-N-hydroxyethylaniline?coupling

Definition

ChEBI: An azo dye with a structure consisting of nitrobenzene substituted on the 4-position of the phenyl group with a 4-[N-ethyl-N-(2-hydroxyethyl)]phenylazo group.

General Description

Disperse Red 1 (DR1) is a non-linear optical (NLO) material which is a chromophore used as an azobenzene dye. It can form a dipole network that can enhance the electro-optic effect of the non-linear components and can also improve the photorefractive effect.

Properties and Applications

Red: dark red powder, melting point 160 ℃ : insoluble in water, but soluble in ethanol, acetone and benzene. The strong sulfuric acid for yellow brown, diluted to deep crimson red; In nitric acid solution for red; In strong hydrochloric acid also to red solution; In the thick of sodium hydroxide solution for the red light brown. Used for polyester and their blended fabric dyeing and printing, also applies to acrylic, polyamide, vinegar fiber, three vinegar fiber dyeing. Used in high temperature and high pressure method and polyester dyeing of carrier. Dyeing rate medium, not sensitive to temperature, have good levelness and lifting force. Can also be used for the wool, plastic, fur color. Standard Ironing Fastness Light Fastness Persperation Fastness Washing Fastness Fading Stain Fading Stain Fading Stain ISO 4 3 4-5 5 5 5 5

Standard

Ironing Fastness

Fading

Stain

ISO

4

InChI:InChI=1/C16H18N4O3/c1-2-19(11-12-21)15-7-3-13(4-8-15)17-18-14-5-9-16(10-6-14)20(22)23/h3-10,21H,2,11-12H2,1H3/b18-17+

Upstream product

• 14368-49-1 p-nitrobenzenediazonium 
• 92-50-2 2-( N-ethylanilino)ethanol 
• 100-01-6 4-nitro-aniline 
• 1355342-65-2 (CH₃)4C₂O₂BC₆H₄CH₂OC₆H₂(C(O)OCH₂CHCH₂)(CH₂OC(O)OCH₂CH₂N(C₂H₅)C₆H₄NNC₆H₄NO₂)CH₂OC(O)N(CH₃)CH₂CH₂N(CH₃)C(O)C₆H₄C₁₃H₆O₂OH 
• 1355342-53-8 (CH₃)4C₂O₂BC₆H₄CH₂OC₆H₂(C(O)OH)(CH₂OC(O)OCH₂CH₂N(C₂H₅)C₆H₄NNC₆H₄NO₂)CH₂OC(O)N(CH₃)CH₂CH₂N(CH₃)C(O)C₆H₄C₁₃H₆O₂OH 
• 622-79-7 benzyl azide 

Downstream Products

• 38777-34-3 p-<(4'-Nitrophenyl)-azo>-(N-ethyl-N-β-bromethyl)-anilin 
• 23946-37-4 N-ethyl-N-(2-aminoethyl)-4-(4-nitrophenylazo)aniline 

Relevant academic research and scientific papers

Photonic crystal fibre as an optofluidic reactor for the measurement of photochemical kinetics with sub-picomole sensitivity

Photonic crystal fibre constitutes an optofluidic system in which light can be efficiently coupled into a solution-phase sample, contained within the hollow core of the fibre, over long path-lengths. This provides an ideal arrangement for the highly sensitive monitoring of photochemical reactions by absorption spectroscopy. We report here the use of UV/vis spectroscopy to measure the kinetics of the photochemical and thermal cis-trans isomerisation of sub-picomole samples of two azo dyes within the 19-μm diameter core of a photonic crystal fibre, over a path length of 30 cm. Photoisomerisation quantum yields are the first reported for "push-pull" azobenzenes in solution at room temperature; such measurements are challenging because of the fast thermal isomerisation process. Rate constants obtained for thermal isomerisation are in excellent agreement with those established previously in conventional cuvette-based measurements. The high sensitivity afforded by this intra-fibre method enables measurements in solvents in which the dyes are too insoluble to permit conventional cuvette-based measurements. The results presented demonstrate the potential of photonic crystal fibres as optofluidic elements in lab-on-a-chip devices for photochemical applications. This journal is

Synthesis and characterization of polythiophene with liquid crystalline azobenzene as side chains

In this study a series of azobenzene-functionalized liquid crystalline (LC) polythiophene derivatives: poly{2-[N-ethyl-N- [4-[4′-(nitrophenyl)azo] phenyl]amino]ethyl-3-thiophene acetate}, Poly(Th3AA-RedI), poly{2-[N-ethyl-N-[4- [4′-(nitrophenyl)azo]-pheny

Six-branched chromophores with isolation groups: Synthesis and enhanced optical nonlinearity

Three new six-branched chromophores with different isolation groups were designed and synthesized by incorporating azo chromophores onto phenyl glycerol ester via an esterification reaction. The chemical structures were confirmed by 1H NMR, 13C NMR, FT-IR spectroscopy, mass spectrometry, element analysis and UV-visible absorption spectra. The six-branched dendritic chromophores can form thin films directly without adding any polymer matrix and show a quite high chromophore loading density. After electric poling, the nonlinear optical coefficients (d33) of the dendrimer films were determined to be around 113, 142 and 136 pm V-1, which are almost 3 times the maximum d33 value of the azo-chromophore doped polymer films. The further improvement in optical nonlinearity was successfully realized by mixing the six-branched chromophores containing different isolation groups.

Preparation of conducting liquid crystalline polymer based of poly(2-ethanol aniline)

The authors prepared a novel conducting liquid crystalline polymer based poly(2-ethanol aniline) by chemical and electrochemical methods. First, 2-anilinoethyl-3-chloropropionate was synthesized by reaction of 2-ethanol aniline and 3-chloropropionate in presence of dicyclohexylcarbodiimide (DCCI) and (dimethylamino)pyridine (DMAP). Then, {2-[ethyl[4-[(4-nitrophenyl)azo] phenyl]amino]ethanol}, Disperse Red-I, (Red1) was prepared from addition of 2-(N-ethyl-N-phenylamine) with the 4-nitrobenzenamine. Potassium salt Red1 was prepared by reaction of potassium and Red1 in THF. Then added to 2-anilinoethyl-3-chloropropionate for chemically synthesis of poly[2-anilino-{3-[2-[ethyl[4-[(4-nitrophenyl)azo]phenyl]amino] propanoate]}], Poly(2AECP-Red1). Produced polymer was characterized using FT-IR, UV-visible, and 1H, 13C-NMR spectroscopies. The thermal and liquid crystalline properties of polymer were studied by thermogravimetric and differential scanning calorimetry. Scanning electron microscopy images supported the formation of polymer and showed morphology feature and homogeneous structure on polymer. Electrical conductivity of Poly(2AECP-Red1) has been studied by four-point probe method and produced 4.9 × 10-3 S/cm conductivity for it.

A simple FRET-based modular design for diagnostic probes

In recent years, there has been a massive effort to develop molecular probes with optical modes of action. Probes generally produce detectable signals based on changes in fluorescence properties. Here, we demonstrate the potential of self-immolative molecular adaptors as a platform for Turn-On probes based on the FRET technique. The probe is equipped with identical fluorophore pairs or a fluorophore/quencher FRET pair and a triggering substrate. Upon reaction of the analyte of interest with the triggering substrate, the self-immolative adaptor spontaneously releases the two dye molecules to break off the FRET effect. As a result, a new measurable fluorescent signal is generated. The fluorescence obtained can be used to quantify the analyte. The modular structure of the probe design will allow the preparation of various chemical probes based on the FRET activation technique.

Nonlinear optical properties and memory effects of the azo polymers carrying different substituents

The third-order nonlinear optical properties and electric memory behavior of azobenzene polymers were influenced by different substituents. The nonlinear optical coefficients of polymer films measured using the Z-scan technique revealed that the polymers with different substituents exhibited different nonlinear absorption. The reversibility of sandwich memory devices based on the azobenzene polymers was dependant on the terminal substituent on the azobenzene chromophore. Polymers with electron-accepting terminal moieties in the azobenzene pendant showed write-once-read-many-times memory whereas the polymer that contained electron-donating moieties displayed a FLASH-type (rewritable) memory.

A FRET-based fluorogenic phosphine for live-cell imaging with the Staudinger ligation

Azide imaging: A fluorogenic phosphine based on a FRET-quenching mechanism allows for live-cell imaging of azido sugars by the Staudinger ligation. This design strategy can accommodate numerous fluorophores and complementary quenchers, enabling extension to multi-color imaging. In the image shown, the nuclei are blue while the cell surfaces and Golgi are green. (Figure Presented).

Perfluoroalkylsulfonyl-Substituted Azobenzenes as Second-Order Nonlinear Optical Chromophores

4-Perfluoroalkylsulfonyl (RfSO2)-substituted azo nonlinear optical chromophores (NLOphores) showed enhanced second-order nonlinear coefficients (d33) and improved relaxation behavior compared with the corresponding nitro compound (Disperse Red 1 (DR1)) in both doped poly(methylmethacrylate) (PMMA) and pendanted methylmethacrylate (MMA) copolymer.