New organic binary solids with phenolic coformers for NLO applications

Abstract

Five binary adducts between N,N-dimethyl-4-[(E)-2-(pyridin-4-yl)ethenyl]aniline) 1, N,N-diethyl-4-[(E)-2-(pyridin-4-yl)ethenyl]aniline) 2, N,N-dimethyl-4-[(E)-pyridin-3-yldiazenyl]aniline 3, and coformers that include 4-nitrophenol I, 4-nitrobenzoic acid II, benzene-1,3-diol III, and 2,4-dinitrophenol IV were synthesized to follow the factors influencing the formation of polar crystals. New solids were characterized by melting points and absorption spectra, while their structures were proven by single crystal X-ray diffraction. Adducts differ by the components' ratio and position of the acidic hydrogen atom, thus giving examples of four new cocrystals and one salt. The single crystal X-ray analysis revealed the acentric packing for two compounds, 1 . (I) and 3(3) . (III) that crystallize in the Pca2 1and P1 space groups. The melting point data and the cut-off wavelength from absorption spectra show that these materials are stable till relatively high temperatures and transparent in a wide range of spectrum.

Crystal structure of 2-[2-(pyridin-3-yl)diazen-1-yl]aniline

“…2,6-diamino-3-[(2-carboxymethyl)phenylazo]pyridine (Tan et al, 2010). 4-Aminophenyl-azopyridines such as N,N-diethyl-4-[(E)-(pyridine-3-yl)diazenyl]aniline (Draguta et al, 2015) and N,N-dimethyl-4-(pyridine-3yldiazenyl)aniline (Draguta et al, 2013) are also known. Furthermore, structure reports on 2-azopyridine molecules that are substituted in the ortho-position, such as 5-[(5-bromo-2-pyridyl)azo]-2,4-toluenediamine (Jinzi et al, 1984) and 5-[(3,5-dibromo-2-pyridyl)azo]-2,4-diaminotoluene (Kailiang et al, 1985), have been published.…”