Perinone

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

Perinone

Identifiers
CAS Number	4424-06-0
3D model (JSmol)	trans isomer: Interactive image
ChemSpider	70517
ECHA InfoCard	100.022.363
EC Number	224-597-4
PubChem CID	78141
CompTox Dashboard (EPA)	DTXSID8025913
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 trans isomer: O=c1n2c3ccccc3nc2c4ccc5c(=O)n6c7ccccc7nc6c8c5c4c1cc8
Properties
Chemical formula	C26H12N4O2
Molar mass	412.408 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

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", CID 78141 from PubChem) and the cis isomer is called Pigment Red 194 ("PR194", CID 77892 from PubChem).[2] Like some structurally related compounds perinone is also an organic semiconductor.[3]

References

1. Mizuguchi, Jin (2004). "Crystal Structure and Electronic Characterization of trans-and cis-Perinone Pigments". J. Phys. Chem. B. 108 (26): 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. Feast, W. James; Peace, Richard J.; Sage, Ian C.; Wood, Emma L. (March 1999). "Poly(4-vinyltriphenylamine): synthesis and application as a hole transport layer in light-emitting diodes". Polymer Bulletin. 42 (2): 167–174. doi:10.1007/s002890050449.