Journal of Fluorescence

, Volume 24, Issue 2, pp 329–335 | Cite as

Synthesis and Spectroscopic Studies of N,N’-dialkyl Derivatives of Antisymmetrical 2H,5H-Dihydropyrrolo[3,4-c]pyrrole-1,4-diones



2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione derivatives (DPP) are chemically stable, fluorescent molecules, known as High Performance Pigments. Preparation of the soluble derivatives of DPPs provides great advantage in designing the optic sensor for new and existing applications and overcoming aggregation problems in solid matrices. For this purpose, the synthesis of antisymmetric DPPs and the formation of new organic dyes through N,N’-dialkylation and their spectroscopic studies have been carried out both in solutions and in solid phase.


High performance pigments Fluorophores Antisymmetric Diketopyrrolopyrrole 



We thank Dokuz Eylul University for support of this work (Scientific Research Project-2007.KB.FEN. 058)


  1. 1.
    Wallquist O, Lenz R (2002) Twenty years of DPP pigments-future perspectives. Macromol Symp 187:617–629CrossRefGoogle Scholar
  2. 2.
    Hao Z, Iqbal A (1997) Some aspects of organic pigments. Chem Soc Rev 26:203–213CrossRefGoogle Scholar
  3. 3.
    Wallquist O (2002) Diketopyrrolopyrrole (DPP) pigments. Wiley-VCH publishers, Verlag GmbH & Co. In High Performance PigmentsGoogle Scholar
  4. 4.
    Maloney J (2002) In: Smith H (ed) Titanate pigments: Colored rutile, priderite and pseudo-brookite structured pigments. Wiley-VCH, Weinheim, pp 159–184Google Scholar
  5. 5.
    Zambounis JS, Hao Z, Iqbal A (1997) Latent pigments activated by heat. Nature (London) 388:131–132CrossRefGoogle Scholar
  6. 6.
    Rochat AC, Wallquist O, Iqbal A, Mizuguchi J (1999) Process for the preparation of aminated diketobis (aryl or heteroaryl)pyrrolopyrroles and the use thereof as photoconductive substances. US Patent 5,973,146Google Scholar
  7. 7.
    Fukuda M, Kodama K, Yamamoto H, Mito K (2002) Solid-state laser with newly synthesized pigment. Dyes Pigments 53:67–72CrossRefGoogle Scholar
  8. 8.
    Fukuda M, Kodama K, Yamamoto H, Mito K (2004) Evaluation of new organic pigments as laser-active media for a solid-state dye laser. Dyes Pigments 63:115–125CrossRefGoogle Scholar
  9. 9.
    Langhals H (1990) Erasable optical fluorescence and absorption data medium having good long-term stability. Ger Pat DE 3901988Google Scholar
  10. 10.
    Mizuguchi J, Rochat CA (1988) A new near-infrared photoreceptor based on 1,4-dithioketo-3,6-diphenyl-Pyrrolo-[3,4-c]-pyrrole. J Imaging Sci 32:135–140Google Scholar
  11. 11.
    Vala M, Vyňuchal J, Toman P, Weiter M, Luňák S Jr (2010) Novel, soluble diphenyl-diketo-pyrrolopyrroles: experimental and theoretical study. Dyes Pigments 84:176–182CrossRefGoogle Scholar
  12. 12.
    Prashant S, Ng G, Lin T, Dodabalapur A, Chen Z (2010) Solution processable low bandgap diketopyrrolopyrrole (DPP) based derivatives: novel acceptors for organic solar cells. J Mater Chem 20:3626–3636CrossRefGoogle Scholar
  13. 13.
    Horn M (1999) Flüssigkristalline pyrrolopyrrol-derivative. Blunk-Verlag, BerlinGoogle Scholar
  14. 14.
    Luňák S, Vyňuchal J, Vala M, Havel L, Hrdina R (2009) The synthesis, absorption and fluorescence of polar diketo-pyrrolo-pyrroles. Dyes Pigments 82:102–108CrossRefGoogle Scholar
  15. 15.
    Vala M, Weiter M, Vynuchal J, Toman P, Lunak S (2008) Comparative studies of diphenyl-diketo-pyrrolopyrrole derivatives for electroluminescence applications. J Fluoresc 18:1181–1186PubMedCrossRefGoogle Scholar
  16. 16.
    Weiter M, Salyk O, Bednar P, Vala M, Navratil J, Zmeskal O, Vynuchal J, Lunak S (2009) Morphology and properties of thin films of diketopyrrolopyrrole derivatives. Mater Sci Eng B 165:148–152CrossRefGoogle Scholar
  17. 17.
    Celik S, Ergun Y, Alp S (2009) Synthesis and spectroscopic studies of 3,6-diphenyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dion’s N, N’-dialkyl derivatives. J Fluoresc 19:829–835PubMedCrossRefGoogle Scholar
  18. 18.
    Williams ATR, Winfield SA, Miller JN (1983) Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer. Analyst 108:1067–1071CrossRefGoogle Scholar
  19. 19.
    Valeur B (2002) Molecular fluorescence: Principles and applications. Wiley-VCH Verlag GmbH, WeinheimGoogle Scholar
  20. 20.
    Horn M, Hepuzer Y, Yagci Y, Bilgin-Eran B, Cernenco U, Harabagiu V, Pinteala M, Simionescu CB (2002) Synthesis and characterisation of thermomesogenic polysiloxanes with 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione units in the main chain. Eur Polymer J 38:2197–2205CrossRefGoogle Scholar
  21. 21.
    Pfenninger J, Iqbal A, Rochat AC (1988) Process for the preparation of pyrrolo[3,4-c]pyrroles. United States Pat. 4.749.795Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of Dokuz Eylul, The Graduate School of Natural and Applied SciencesIzmirTurkey
  2. 2.Department of ChemistryUniversity of Dokuz Eylul, Faculty of SciencesIzmirTurkey

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