Perinone

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

Perinone
trans-Perinone. cis mirrors one half top-to-bottom
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.363
EC Number
  • 224-597-4
  • 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
  • trans isomer: O=c1n2c3ccccc3nc2c4ccc5c(=O)n6c7ccccc7nc6c8c5c4c1cc8
Properties
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. S2CID 95994481.
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