1,2,4,5-TETRACYANOBENZENE

Chemical Properties

solid

Uses

1,2,4,5-Tetracyanobenzene (TCB, TCNB) is suitable reagent used in the synthesis of o-3,4-dimethyltetrathiafulvalene (o-Me₂TTF)-1,2,4,5-tetracyanobenzene (TCNB) 1:1 complex and radiative exciplexes of TCB in non-polar solvents.

1,2,4,5-Tetracyanobenzene (Pyromellitic acid tetranitrile, PMTN, TCB, TCNB, 1,2,4,5-benzenetetracarbonitrile ) may be used in the following studies:

• Solid-state diffusion of TCNB into 9-methylanthracene molecular crystal nanorods forming cocrystal nanorods.
• Synthesis of copper polyphthalocyanine (CuPPC) thin films, an elementoorganic semiconductor.
• Preparation of charge transfer (CT) nanocrystallites which may have a potential use in nanofluidics to observe the rotational motion of nanoobjects.
• Hydrothermal synthesis of Co₂(terpy)₂(btec)?H₂O (terpy = 2,2′:6′,2"-terpyridine, btec = 1,2,4,5-benzenetetracarboxylate).

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 3520, 1962 DOI: 10.1021/jo01057a028

General Description

1,2,4,5-Tetracyanobenzene (TCNB, TCB) is a tetra substituted benzene. The IR and raman spectra of TCNB and its 1:1 complex with durene has been recorded. The time-resolved linear dichroism spectroscopic study of hexamethylbenzene-1,2,4,5-tetracyanobenzene charge-transfer complex has been investigated. The influence of magnetic field on the charge-transfer fluorescence of 1,2,4,5-tetracyanobenzene-doped poly(N-vinylcarbazole) thin film has been studied.

Purification Methods

Crystallise the tetra-nitrile from EtOH and sublime in vacuo. [Lawton & McRitchie J Org Chem 24 26 1959, Bailey et al. Tetrahedron 19 161 1963, Beilstein 9 IV 3800.]