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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
990:
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;
610:
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.
625:
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
408:
633:
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.
725:
1068:
284:
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572:
557:
542:
524:. The latter is oxidized to quinacridone. Derivatives of quinacridone can be readily obtained by employing substituted anilines. Linear
99:
742:
249:
996:
640:
and Cl substituents. Some magenta shades of quinacridone are labeled under the proprietary name "Thio Violet" and "Acra Violet".
629:
than the α crystal phase. The γ crystal modification is characterized by a criss-cross lattice where each quinacridone molecule
1053:
669:
1073:
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)
841:
Lomax, Suzanne
Quillen (13 December 2013). "Phthalocyanine and quinacridone pigments: their history, properties and use".
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415:
661:
192:
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656:. These properties complement good photo-, thermal, and electrochemical stability. These properties are desired for
213:
1058:
509:
149:
464:. As pigments, the quinacridones are insoluble. The development of this family of pigments supplanted the
814:
Lincke, Gerhard (2002). "On quinacridones and their supramolecular mesomerism within the crystal lattice".
607:
438:. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial
137:
969:
Chenguang, Wang; Zuolun, Zhang; Yue, Wang (2016). "Quinacridone-based π-conjugated electronic materials".
885:
684:
1008:
673:
39:
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484:, although they are not made that way. Classically the parent is prepared from the 2,5-dianilide of
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665:
1024:
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485:
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E.F. Paulus; F.J.J. Leusen & M.U. Schmidt (2007). "Crystal structures of quinacridones".
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978:
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999:(2013). "Hydrogen-Bonded Semiconducting Pigments for Air-Stable Field-Effect Transistors".
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75:
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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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700:, self-assembled quinacridone chains on a graphite background.
218:
672:(OFETs). Due to interplay of intermolecular H-bonding and
614:
dispersions of quinacridone pigments functionalized with
941:"The Color of Art Pigment Database: Pigment Violet - PV"
403:
787:
Labana, S. S.; Labana, L. L. (1967). "Quinacridones".
476:
The name indicates that the compounds are a fusion of
723:
Hunger, K.; Herbst, W. (2012). "Pigments, Organic".
180:
520:affords dihydroquinacridone, which are readily
74:
726:Ullmann's Encyclopedia of Industrial Chemistry
8:
442:applications such as robust outdoor paints,
621:are the most common magenta printing ink.
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233:
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18:
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718:
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648:Quinacridone derivatives exhibit intense
200:
691:
292:O=C4c5ccccc5Nc3cc2C(=O)c1c(cccc1)Nc2cc34
44:5,12-Dihydroquinolinoacridine-7,14-dione
712:
289:
254:
229:
131:
261:Key: NRCMAYZCPIVABH-UHFFFAOYSA-N
7:
915:"handprint : watercolor brands"
541:
528:-Quinacridones can be prepared from
1069:Heterocyclic compounds with 5 rings
855:10.1179/sic.2005.50.Supplement-1.19
271:Key: NRCMAYZCPIVABH-UHFFFAOYAK
171:
16:Organic compound used as a pigment
14:
652:in the dispersed state, and high
670:organic field-effect transistors
586:
571:
556:
393:
325:
319:
25:
389:(at 25 °C , 100 kPa).
331:
313:
53:C.I.: 73900, Pigment Violet 19
1:
828:10.1016/S0143-7208(01)00085-7
698:scanning tunneling microscope
662:organic light-emitting diodes
357:Red powder (nanoparticles)
1095:
676:, quinacridone can form a
997:Sarıçiftçi, Niyazi Serdar
383:
300:
280:
245:
58:
50:
38:
33:
24:
735:10.1002/14356007.a20_371
644:Semiconductor properties
627:thermodynamically stable
843:Studies in Conservation
750:(subscription required)
729:. Weinheim: Wiley-VCH.
660:applications including
510:succinosuccinate esters
1054:Organic semiconductors
1021:10.1002/adma.201204039
763:"Quinacridone Colours"
701:
1074:Nitrogen heterocycles
695:
685:organic semiconductor
508:). Condensation of
40:Preferred IUPAC name
1013:2013AdM....25.1563G
801:10.1021/cr60245a001
666:organic solar cells
602:Quinacridone-based
459:color laser printer
374:Solubility in water
349: g·mol
21:
1001:Advanced Materials
983:10.1039/C6TC03621J
963:Additional reading
702:
416:Infobox references
19:
971:J. Mater. Chem. C
919:www.handprint.com
816:Dyes and Pigments
767:Jane Blundell.com
600:
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486:terephthalic acid
455:watercolor paints
424:Chemical compound
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214:CompTox Dashboard
100:Interactive image
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1059:Organic pigments
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913:MacEvoy, Bruce.
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789:Chemical Reviews
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761:Blundell, Jane.
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432:organic compound
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945:Art is Creation
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891:10.1.1.589.5547
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849:(sup1): 19–29.
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1007:(11): 1563–9.
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939:Myers, David.
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20:Quinacridone
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1000:
993:Torsi, Luisa
974:
970:
948:. Retrieved
944:
934:
922:. Retrieved
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881:
878:CrystEngComm
877:
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770:. Retrieved
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668:(OSCs), and
650:fluorescence
647:
635:
623:
616:solubilizing
601:
593:
578:
563:
548:
525:
516:followed by
475:
428:Quinacridone
427:
426:
59:Identifiers
51:Other names
696:Taken by a
619:surfactants
536:Derivatives
518:cyclization
453:, artists'
451:tattoo inks
447:printer ink
354:Appearance
301:Properties
138:100.012.618
1048:Categories
884:(2): 131.
707: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
1079:Acridines
1064:Diketones
1037:205247943
950:4 October
924:4 October
886:CiteSeerX
664:(OLEDs),
482:quinoline
472:Synthesis
159:213-879-2
151:EC Number
76:1047-16-1
1029:23239229
863:97211023
795:: 1–18.
772:1 August
604:pigments
596:-Isomer
592:Angular
581:-Isomer
577:Angular
566:-Isomer
551:-Isomer
478:acridone
466:alizarin
440:colorant
1009:Bibcode
608:Du Pont
562:Linear
547:Linear
514:aniline
436:pigment
409:what is
407: (
363:Density
347:312.328
169:PubChem
1035:
1027:
888:
861:
741:
496:(NHPh)
468:dyes.
457:, and
444:inkjet
430:is an
404:verify
401:
285:SMILES
34:Names
1033:S2CID
859:S2CID
594:trans
549:trans
512:with
462:toner
250:InChI
182:13976
120:13369
89:JSmol
1025:PMID
952:2019
926:2019
774:2018
739:ISBN
480:and
193:UNII
1017:doi
979:doi
896:doi
851:doi
824:doi
797:doi
731:doi
687:.
579:cis
564:cis
526:cis
500:(CO
219:EPA
172:CID
1050::
1031:.
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1005:25
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502:2
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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