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Synthesis of 4-[4-(4-nitrobenzylideneiminophenylene)phenyleneimino methylidene] phenol

Romanian Academy, “Petru Poni” Institute of Macromolecular Chemistry, Aleea Gr. Ghica Voda 41A, Iasi 700487, Romania
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Author to whom correspondence should be addressed.
Molbank 2006, 2006(5), M488; https://doi.org/10.3390/M488
Submission received: 26 October 2005 / Accepted: 13 January 2006 / Published: 1 September 2006
The azomethine 1 was prepared as described elsewhere [1]. The 4-[4-(4-nitrobenzylidene- iminophenylene)phenyleneimino methylidene] phenol (2) was obtained in a similar manner [2] by reacting the azomethine 1 with 4-nitrobenzaldehyde in stoichiometric ratio:
Molbank 2006 m488 i001
A mixture of 0.8 g (2.88 mmol) 1 and 0.42 g (2.77 mmol) 4-nitrobenzaldehyde was dissolved in 10 mL DMSO. The mixture was stirred under heating at 90 °C for 30 min. The reaction product was isolated by pouring the reaction mixture into water, washing with water and then with methanol. The purity was tested by the thin layer chromatography. IR spectra and elemental analysis confirmed that synthesised compound had the correct structure with a good degree of purity. The azomethine 2 has an orange-ochre powder aspect , yield 80 %.
Mp. 213 °C (by polarization light microscopy), 212 °C (by thermooptical analysis), 215 °C (by DSC method). In the melting state the product exhibit liquid crystalline behavior displaying a typical schlieren texture (see Figure 1). The isotropisation temperature could not be measured, because the decomposition started before (decomposition temperature To = 256°C)
UV (DMF) 286, 382 nm
Anal. calc. for C26H19N3 O3 (421.45): N % 9.97; found: N % 9.52
IR (KBr, cm−1): 3450 (O-H), 1625 (CH=N), 1600, 1580 (C=C), 1520 (NO2 asym.), 1450 (C=C), 1350 (NO2 sym.), 1240 (C-O, asym.), 1160 (C-O, sym.), 855, 840 (1,4-phenylene ring).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References:

  1. Cozan, V.; Avram, E. Eur. Polym. J. 2003, 39, 107–114.
  2. Racles, C.; Cozan, V. High Performance Polymers 2002, 14, 169–181.
Figure 1. The schlieren texture of azomethine 2 at 246 °C, between crossed polarizers
Figure 1. The schlieren texture of azomethine 2 at 246 °C, between crossed polarizers
Molbank 2006 m488 g001

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MDPI and ACS Style

Marin, L.; Cozan, V. Synthesis of 4-[4-(4-nitrobenzylideneiminophenylene)phenyleneimino methylidene] phenol. Molbank 2006, 2006, M488. https://doi.org/10.3390/M488

AMA Style

Marin L, Cozan V. Synthesis of 4-[4-(4-nitrobenzylideneiminophenylene)phenyleneimino methylidene] phenol. Molbank. 2006; 2006(5):M488. https://doi.org/10.3390/M488

Chicago/Turabian Style

Marin, L., and V. Cozan. 2006. "Synthesis of 4-[4-(4-nitrobenzylideneiminophenylene)phenyleneimino methylidene] phenol" Molbank 2006, no. 5: M488. https://doi.org/10.3390/M488

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