Perinone

Perinone

Identifiers
CAS Number	4424-06-0
3D model (Jmol)	Interactive image
ChemSpider	70517
ECHA InfoCard	100.022.363
EC Number	224-597-4
PubChem	78141
InChI InChI=1S/C26H12N4O2/c31-25-15-12-10-14-22-16(26(32)30-20-8-4-2-6-18(20)28-24(14)30)11-9-13(21(15)22)23-27-17-5-1-3-7-19(17)29(23)25/h1-12H Key: DGBWPZSGHAXYGK-UHFFFAOYSA-N InChI=1/C26H12N4O2/c31-25-15-12-10-14-22-16(26(32)30-20-8-4-2-6-18(20)28-24(14)30)11-9-13(21(15)22)23-27-17-5-1-3-7-19(17)29(23)25/h1-12H Key: DGBWPZSGHAXYGK-UHFFFAOYAN
SMILES C1=CC=C2C(=C1)N=C3N2C(=O)C4=CC=C5C6=C(C=CC3=C46)C(=O)N7C5=NC8=CC=CC=C87
Properties
Chemical formula	C26H12N4O2
Molar mass	412.41 g·mol^−1
Appearance	Orange solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Perinone is a class of organic compounds. The parent compound has two isomers, each of which are useful pigments.

It is prepared from naphthalenetetracarboxylic dianhydride by condensation with o-phenylenediamine. The two Isomers of perinone^[1] are useful pigments. The trans isomer is called Pigment Orange 43 ("PO43") and the cis isomer is called Pigment Red 194 ("PR194").^[2] Like some structurally related compounds perinone is also an organic semiconductor.^[3]

References

1. Jin Mizuguchi Crystal Structure and Electronic Characterization of trans-and cis-Perinone Pigments J. Phys. Chem. B 2004, vol. 108, pp. 8926–8930. doi:10.1021/jp031351d
2. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
3. W. James Feast et al.: Poly(4-vinyltriphenylamine): synthesis and application as a hole transport layer in light-emitting diodes. In: Polymer Bulletin 42, 1999, S. 167–174.