13103-75-8

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4606, 1951 DOI: 10.1021/ja01154a031

InChI:InChI=1/C13H14N4/c1-17(2)12-8-6-11(7-9-12)15-16-13-5-3-4-10-14-13/h3-10H,1-2H3/b16-15+

Upstream product

• 504-29-0 2-aminopyridine 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 91-20-3 naphthalene 
• 108-88-3 toluene 
• 13103-75-8 N,N-dimethyl-4-([2]pyridyl-cis-azo)-aniline 
• 77038-70-1 pyridine-azo-p-dimethyl aniline 

Downstream Products

• 77038-70-1 pyridine-azo-p-dimethyl aniline 
• 109401-83-4 N,N-dimethyl-4-(1-oxy-[2]pyridylazo)-aniline-N-oxide 
• 890710-13-1 Br^(1-)*C₁₆H₂₀BrN₄⁽¹⁺⁾ 
• 13103-75-8 N,N-dimethyl-4-([2]pyridyl-cis-azo)-aniline 
• 863638-71-5 Br^(1-)*C₁₉H₂₆BrN₄⁽¹⁺⁾ 

Relevant academic research and scientific papers

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.

Photoactive azoimine dyes: 4-(2-Pyridylazo)-N,N-diethylaniline and 4-(2-pyridylazo)-N,N-dimethylaniline: Computational and experimental investigation

4-(2-Pyridylazo)-N,N-dimethylaniline and 4-(2-pyridylazo)-N,N- diethylaniline, two photoactive azoimine dyes, were prepared from the reaction of 2-aminopyridine with N,N-dialkyl-1,4-nitrosoaniline at room temperature. Structural characterizations of these dyes using single crystal X-ray diffraction, 1H NMR, elemental analysis, mass spectroscopy and IR spectroscopy have been carried out. The X-ray structure indicates a trans configuration around the azo group. The photochemical behavior of these compounds differs from that of 2-phenylazopyridine, the non-dialkylamino substituent compound. The synthesized compounds show emission spectra at room temperature while 2-phenylazopyridine does not. The excitation spectra of these compounds differ from their absorption spectra which can be explained on the basis of the trans to cis photoisomerization which is supported by the TD-PBE0/6-31G(d,p) calculations. Both oxidation of the dialkylamino substituents (-NR2; R = -CH3 and -C2H5) and reduction of -NN-/-NN-- and -NN--/-NN-2- were observed in the cyclic voltammogram indicating a π-acidity of both dyes.