253333-13-0

Basic information

• Product Name: Phenol, 4-[(1E)-4-pyridinylazo]-
• CAS NO: 253333-13-0
• Molecular Formula: C11H9N3O
• Molecular Weight: 199.212
• Mol File: 253333-13-0.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 4-[(1E)-4-pyridinylazo]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 4-[(1E)-4-pyridinylazo]-(253333-13-0)
• EPA Substance Registry System: Phenol, 4-[(1E)-4-pyridinylazo]-(253333-13-0)

Safety Data

• Hazardous Substances Data: 253333-13-0(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 20815-66-1 4-(4-hydroxyphenylazo)pyridine 
• 504-24-5 4-aminopyridine 
• 20815-53-6 4-(4-chlorophenylazo)pyridine 

Downstream Products

• 20815-66-1 4-(4-hydroxyphenylazo)pyridine 
• 1403494-63-2 C₁₇H₂₃N₃OSi 
• 924964-13-6 4-((4-methacryloyloxy)phenylazo)pyridine 

Relevant articles and documents

Azopyridine-functionalized benzoxazine with Zn(ClO4)2 form high-performance polybenzoxazine stabilized through metal-ligand coordination

In this study, we prepared a benzoxazine monomer (Azopy-BZ) that features azobenzene and pyridine units through the reaction of paraformaldehyde, aniline, and 4-(4-hydroxphenylazo)pyridine (Azopy-OH), which is obtained through a diazonium reaction of 4-am

Is chemical crosslinking necessary for the photoinduced bending of polymer films?

Freestanding crosslinked liquid-crystalline polymer films obtained by self-assembly through intermolecular hydrogen bonding showed photoinduced bending and unbending. The structural change at the microscopic level, caused by trans-cis photoisomerization of the azobenzene moieties at the hydrogen-bonded crosslinks, is successfully converted into a macroscopic deformation in the liquid-crystalline polymer films. The Royal Society of Chemistry.

A modular approach towards functional supramolecular aggregates-subtle structural differences inducing liquid crystallinity

Herein we report an efficient modular approach to supramolecular functional materials. Hierarchical self-assembly of azopyridine derivatives and hydrogen-bond donors yielded discotic assemblies. Subtle differences in the core units introduced mesomorphic

A multi-responsive organogel and colloid based on the self-assembly of a Ag(i)-azopyridine coordination polymer

In this work, through the coordination ofC3symmetric azopyridine ligands and Ag(i), coordination polymers with azo groups on the main chain were prepared. Thetranscoordination polymer formed an organogel with a network of nanofibers at low crit

Hydrogen bonding interactions affect the hierarchical self-assembly and secondary structures of comb-like polypeptide supramolecular complexes displaying photoresponsive behavior

In this study we blended 4-(4-hexadecylphenylazo)pyridine (AzoPy-C16), synthesized through facile diazonium and monoetherification reactions, with polytyrosine (PTyr) to form comb-like polypeptide supramolecular complexes stabilized through hydrogen bonding between the pyridyl ring of each AzoPy-C16 unit and the OH groups of PTyr. The secondary structure of PTyr transformed from an α-helical to a β-sheet conformation upon the addition of AzoPy-C16, because the long alkyl chains of the AzoPy-C16 units disrupted the weak intramolecular hydrogen bonds between the CO and NH groups in the α-helical conformation, as determined using Fourier transform infrared (FTIR) and circular dichroism (CD) spectroscopy. Small-angle X-ray scattering (SAXS) and wide-angle X-ray diffraction (WAXD) suggested a hierarchical lamellae-within-lamellae structure for the PTyr/AzoPy-C16 supramolecular complex, featuring long-range-ordered lamellae arising from the antiparallel β-pleated sheet conformation of PTyr (d = 1.15 nm) within long-range-ordered lamellae arising from the alkyl groups of AzoPy-C16 units (d = 5.94 nm), oriented in a perpendicular manner. The d-spacing and long-range order of the lamellar structure formed from the alkyl groups decreased upon UV irradiation as the rod-like trans isomers of the AzoPy-C16 units transformed into V-shaped cis counterparts. This phenomenon also led to a change in the water contact angle of the supramolecular material, with the hydrophobic surface of PTyr/trans-AzoPy-C16 (94.2°) transforming to a hydrophilic surface for PTyr/cis-AzoPy-C16 (61.3°).

Tuning the photonic properties of chiral nematic mesoporous organosilica with hydrogen-bonded liquid-crystalline assemblies

A series of novel hydrogen-bonded assemblies was synthesized and characterized with respect to their liquid-crystalline behaviour. Solid-state NMR spectroscopy gave insight into the columnar nematic mesophase and the corresponding ordering and alignment.

Light-controlled real time information transmitting systems based on nanosecond thermally-isomerising amino-azopyridinium salts

Aminoazopyridines are valuable molecules for stable information transmitting systems as well as for light-controlled optical oscillators. Amino-substituted azopyridinium methyl iodide salts transmit optical information within the time scale of nanoseconds, and moreover, show oscillation frequencies up to 1 MHz at room temperature.

Azo dyes functionalized with alkoxysilyl ethers as chemodosimeters for the chromogenic detection of the fluoride anion

Finding fluoride: An azo dye functionalized with tert-butyldimethylsilyl ether has been synthesized and used as a selective chromogenic fluoride sensor in the acetonitrile/water mixtures. The chromogenic response arises from the fluoride-induced hydrolysi

Photo-driven optical oscillators in the kHz range based on push-pull hydroxyazopyridines

Push-pull azophenols are valuable target molecules for stable photo-driven optical oscillators. Hydroxyazopyridinium methyl iodide salts show oscillation frequencies up to 10 kHz with no signs of fatigue upon continuous work. The Royal Society of Chemistry.

Azobenzene-containing molecularly imprinted polymer microspheres with photoresponsive template binding properties

The first successful preparation of azobenzene (azo)-containing molecularly imprinted polymer (MIP) microspheres with photoresponsive template binding properties is described. A methacrylate azo functional monomer with a pyridine group was used for this purpose, and its good solubility in acetonitrile allowed the implementation of molecular imprinting via precipitation polymerization, leading to azo-containing MIP microspheres (number-average diameter = 1.33 μm, polydispersity index = 1.15) with obvious molecular imprinting effects towards the template 2,4-dichlorophenoxyacetic acid (2,4-D), rather fast template rebinding kinetics, and appreciable selectivity over structurally related compounds. The binding association constant Ka and apparent maximum number Nmax for high-affinity sites of the imprinted polymer in the dark environment were determined by Scatchard analysis to be 2.3 × 104 M-1 and 10.0 μmol g-1, respectively. Most importantly, the binding affinity of the imprinted sites in azo-containing MIP microspheres was found to be photoresponsive towards the template, which decreased upon UV light irradiation (as revealed by the resulting lower K a value for high-affinity sites and reduced specific bindings), whereas it could be recovered during the subsequent thermal (or visible light-induced) back-isomerization. Furthermore, this photoregulation process proved to be highly repeatable under photoswitching conditions. The Royal Society of Chemistry.