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Perinone

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Perinone
trans-Perinone. cis mirrors one half top-to-bottom
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.363 Edit this at Wikidata
EC Number
  • 224-597-4
PubChem CID
CompTox Dashboard (EPA)
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/h1-12HKey: 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/h1-12HKey: DGBWPZSGHAXYGK-UHFFFAOYAN
SMILES
  • trans isomer: O=c1n2c3ccccc3nc2c4ccc5c(=O)n6c7ccccc7nc6c8c5c4c1cc8
Properties
Chemical formula C26H12N4O2
Molar mass 412.408 g·mol
Appearance Orange solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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 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). Like some structurally related compounds perinone is also an organic semiconductor.

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. S2CID 95994481.
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