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Typically deep red to violet in color, the hue of quinacridone is affected not only by the R-groups on the molecule but by the crystal form of the solid. For example, the Îł crystal modification of unsubstituted quinacridone provides a strong red shade that has excellent color fastness and resistance
997:
GĹ‚owacki, Eric Daniel; Irimia-Vladu, Mihai; Kaltenbrunner, Martin; Gsiorowski, Jacek; White, Matthew S.; Monkowius, Uwe; Romanazzi, Giuseppe; Suranna, Gian Paolo; Mastrorilli, Piero; Sekitani, Tsuyoshi; Bauer, Siegfried; Someya, Takao;
617:
in 1958. Quinacridones are considered "high performance" pigments because they have exceptional color and weather fastness. Major uses for quinacridones include automobile and industrial coatings.
632:
to solvation. Another important modification is the β phase which provides a maroon shade that is also more weather resistant and light-fast. Both crystal modifications are more
640:
to four neighbors via single H-bonds. The β phase, meanwhile, consists of linear chains of molecules with double H-bonds between each quinacridone molecule and two neighbors.
408:
732:
1075:
284:
524:. The latter is oxidized to quinacridone. Derivatives of quinacridone can be readily obtained by employing substituted anilines. Linear
99:
647:
and Cl substituents. Some magenta shades of quinacridone are labeled under the proprietary name "Thio Violet" and "Acra Violet".
636:
than the α crystal phase. The γ crystal modification is characterized by a criss-cross lattice where each quinacridone molecule
258:
InChI=1S/C20H12N2O2/c23-19-11-5-1-3-7-15(11)21-17-10-14-18(9-13(17)19)22-16-8-4-2-6-12(16)20(14)24/h1-10H,(H,21,23)(H,22,24)
268:
InChI=1/C20H12N2O2/c23-19-11-5-1-3-7-15(11)21-17-10-14-18(9-13(17)19)22-16-8-4-2-6-12(16)20(14)24/h1-10H,(H,21,23)(H,22,24)
848:
Lomax, Suzanne
Quillen (13 December 2013). "Phthalocyanine and quinacridone pigments: their history, properties and use".
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579:
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403:
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663:. These properties complement good photo-, thermal, and electrochemical stability. These properties are desired for
249:
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415:
1060:
676:
1080:
704:
464:. As pigments, the quinacridones are insoluble. The development of this family of pigments supplanted the
821:
Lincke, Gerhard (2002). "On quinacridones and their supramolecular mesomerism within the crystal lattice".
668:
438:. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial
192:
137:
976:
Chenguang, Wang; Zuolun, Zhang; Yue, Wang (2016). "Quinacridone-based π-conjugated electronic materials".
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509:
149:
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484:, although they are not made that way. Classically the parent is prepared from the 2,5-dianilide of
230:
699:
892:
614:
883:
E.F. Paulus; F.J.J. Leusen & M.U. Schmidt (2007). "Crystal structures of quinacridones".
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1006:(2013). "Hydrogen-Bonded Semiconducting Pigments for Air-Stable Field-Effect Transistors".
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201:
119:
39:
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8:
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Basic modifications to the chemical structure of quinacridones include the addition of CH
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are used to make high performance paints. Quinacridones were first sold as pigments by
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Except where otherwise noted, data are given for materials in their
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707:, self-assembled quinacridone chains on a graphite background.
26:
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679:(OFETs). Due to interplay of intermolecular H-bonding and
621:
dispersions of quinacridone pigments functionalized with
948:"The Color of Art Pigment Database: Pigment Violet - PV"
794:
Labana, S. S.; Labana, L. L. (1967). "Quinacridones".
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The name indicates that the compounds are a fusion of
730:
Hunger, K.; Herbst, W. (2012). "Pigments, Organic".
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180:
520:affords dihydroquinacridone, which are readily
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733:Ullmann's Encyclopedia of Industrial Chemistry
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442:applications such as robust outdoor paints,
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628:are the most common magenta printing ink.
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140:
118:
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725:
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655:Quinacridone derivatives exhibit intense
200:
939:
841:
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292:O=C4c5ccccc5Nc3cc2C(=O)c1c(cccc1)Nc2cc34
44:5,12-Dihydroquinolinoacridine-7,14-dione
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229:
1053:
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820:
720:
131:
969:
847:
261:Key: NRCMAYZCPIVABH-UHFFFAOYSA-N
922:"handprint : watercolor brands"
767:
528:-Quinacridones can be prepared from
1076:Heterocyclic compounds with 5 rings
919:
862:10.1179/sic.2005.50.Supplement-1.19
271:Key: NRCMAYZCPIVABH-UHFFFAOYAK
171:
13:
16:Organic compound used as a pigment
14:
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659:in the dispersed state, and high
677:organic field-effect transistors
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25:
389:(at 25 °C , 100 kPa).
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331:
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53:C.I.: 73900, Pigment Violet 19
1:
835:10.1016/S0143-7208(01)00085-7
713:
705:scanning tunneling microscope
669:organic light-emitting diodes
471:
7:
357:Red powder (nanoparticles)
10:
1102:
683:, quinacridone can form a
1004:Sarıçiftçi, Niyazi Serdar
383:
300:
280:
245:
58:
50:
38:
33:
24:
742:10.1002/14356007.a20_371
651:Semiconductor properties
634:thermodynamically stable
543:Isomers of quinacridone
850:Studies in Conservation
757:(subscription required)
736:. Weinheim: Wiley-VCH.
667:applications including
510:succinosuccinate esters
1061:Organic semiconductors
1028:10.1002/adma.201204039
770:"Quinacridone Colours"
708:
1081:Nitrogen heterocycles
702:
692:organic semiconductor
508:). Condensation of
40:Preferred IUPAC name
1020:2013AdM....25.1563G
808:10.1021/cr60245a001
673:organic solar cells
609:Quinacridone-based
459:color laser printer
374:Solubility in water
349: g·mol
21:
1008:Advanced Materials
990:10.1039/C6TC03621J
970:Additional reading
709:
416:Infobox references
19:
978:J. Mater. Chem. C
926:www.handprint.com
823:Dyes and Pigments
774:Jane Blundell.com
607:
606:
486:terephthalic acid
455:watercolor paints
424:Chemical compound
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214:CompTox Dashboard
100:Interactive image
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1066:Organic pigments
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661:carrier mobility
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530:isophthalic acid
432:organic compound
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984:(42): 9918–36.
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952:Art is Creation
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898:10.1.1.589.5547
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856:(sup1): 19–29.
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751:978-3527306732
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681:pi-pi stacking
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20:Quinacridone
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1000:Torsi, Luisa
981:
977:
955:. Retrieved
951:
941:
929:. Retrieved
925:
915:
888:
885:CrystEngComm
884:
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843:
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777:. Retrieved
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675:(OSCs), and
657:fluorescence
654:
642:
630:
623:solubilizing
608:
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585:
570:
555:
525:
516:followed by
475:
428:Quinacridone
427:
426:
59:Identifiers
51:Other names
703:Taken by a
626:surfactants
536:Derivatives
518:cyclization
453:, artists'
451:tattoo inks
447:printer ink
354:Appearance
301:Properties
138:100.012.618
1055:Categories
891:(2): 131.
714:References
434:used as a
379:Insoluble
367:1.47 g/cm
342:Molar mass
202:11P487375P
111:ChemSpider
87:3D model (
66:CAS Number
1086:Acridines
1071:Diketones
1044:205247943
957:4 October
931:4 October
893:CiteSeerX
671:(OLEDs),
482:quinoline
472:Synthesis
159:213-879-2
151:EC Number
76:1047-16-1
1036:23239229
870:97211023
802:: 1–18.
779:1 August
611:pigments
603:-Isomer
599:Angular
588:-Isomer
584:Angular
573:-Isomer
558:-Isomer
478:acridone
466:alizarin
440:colorant
1016:Bibcode
615:Du Pont
569:Linear
554:Linear
514:aniline
436:pigment
409:what is
407: (
363:Density
347:312.328
169:PubChem
1042:
1034:
895:
868:
748:
496:(NHPh)
468:dyes.
457:, and
444:inkjet
430:is an
404:verify
401:
285:SMILES
34:Names
1040:S2CID
866:S2CID
601:trans
556:trans
512:with
462:toner
250:InChI
182:13976
120:13369
89:JSmol
1032:PMID
959:2019
933:2019
781:2018
746:ISBN
480:and
193:UNII
1024:doi
986:doi
903:doi
858:doi
831:doi
804:doi
738:doi
694:.
586:cis
571:cis
526:cis
500:(CO
219:EPA
172:CID
1057::
1038:.
1030:.
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1012:25
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498:2
494:2
492:H
490:6
399:Y
335:2
332:O
329:2
326:N
320:H
314:C
221:)
217:(
91:)
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