Perinone

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Perinone
trans-Perinone.  cis mirrors one half top-to-bottom
PO43 Orange périnone b.jpg
Identifiers
  • 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
Properties
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", 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. 
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