(1E,2E)-1,2-Bis[1-(3-nitrophenyl)ethylidene]hydrazine

Abstract

The asymmetric unit of the title compound, C16H14N4O4, contains one half-mol­ecule of (nitro­phen­yl)ethanimine and the complete mol­ecule is generated by a crystallographic inversion centre. The mol­ecule has an E conformation with respect to each C=N double bond. The central C=N—N=C plane is twisted from the benzene rings with a dihedral angle of 24.76 (11)°. In the crystal, C—H⋯O inter­actions link the molecules to form sheets that lie parallel to (10-4).

Origin and switch of different colors: Thermo-isomerism and crystal structure of (1E,2E)-bis[1-(4-nitrophenyl)ethylidene] hydrazine

“…Our strategy was to develop a simple and acceptable procedure, in one step, to prepare the desired colored compound (1). The result of our investigation is given below (scheme 1).…”

“…π-conjugated fluorescent compounds with C=N-N=C moiety can be useful models for fluorescent electronic and bio-materials. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] A list of known π-conjugated compounds is given in Supplementary Information (figure S1). The concept of a fluorescent material is fundamentally based on intramolecular charge transfer that occurs in its simplest form in π-conjugated hydrazone systems.…”

“…The concept of a fluorescent material is fundamentally based on intramolecular charge transfer that occurs in its simplest form in π-conjugated hydrazone systems. Hydrazones have been intensively investigated mostly because of their potential applications [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] as antimicrobial agents and as fluorescent chemosensors * For correspondence for metal ions. The title compound was synthesized to study antibacterial activity and fluorescence properties in order to get more detail on the structure-activity relationship by comparison with other closely related compounds.…”

“…In search of new bioactive π-conjugated fluorescent compounds to study the difference between fluorescent and normal bioactive agents, we have considered the simple case of compound (1). Cooperation between terminal substituents of phenyl groups played a key role in the trans-cis isomerism even though fluorescent compounds are used in these systems.…”