Crystal Phase Study of Pigment Red 254 in the Presence of Ionic ‎Liquids

Journal: Vol.5, No.1, Winter 2012 - Article 1   Pages :   Until 

Article Code:

S. Shiva Shamekhi: Institute for Color Science and Technology - Department of Organic Colorants
Farahnaz Nourmohammadian: Institute of Color Science and Technology - Department of Organic Colorants

Article's abstract:

Different crystal phase with a same chemical structure, polymorphous, is a specific physical characteristic which determine the end usage of pigments especially in high performance ones. Diketopyrrolopyrrole DPP derivatives, as one of the innovative in heterocyclic pigments, follow this pattern. Synthesis of pigment red 254 in selected crystal phase using ionic liquids was achieved without any further phase separation steps after synthesis. Observed different physical properties such as melting points, color properties of these synthesized pigmentsPR 254 in α and β phases are clarified .

Diketopyrrolopyrrole, Crystal modification, Ionic liquids, Pigment Red 254.

1. A. C. Rochat, L. Cassar, A. Iqbal, Preparation of pyrrolo [3, 4-c] pyrroles,. US Pat. 4, 579,949, 1986.#2. S. L. Jr, J. Vyňuchal, M. Vala, L. Havel, R. Hrdina, The synthesis, absorption and fluorescence of polar diketo-pyrrolo-pyrroles, Dyes Pigm., 82(2009), 102-108.#3. M. Smith, High performance pigments, VCH, Inc., NewYork, 2002.#4. D. Cao, Q. Liu, W. Zeng, Sh. Han, J. Peng, Sh. Liu, Part A: polymer chemistry, synthesis and characterization of novel red-emitting alternating copolymers based on fluorene and diketopyrrolopyrrole Derivatives, J. Polym. Sci., 44(2006), 2395-2405.#5. G. Q. Zhang, K. Liu, Y. Li, M. J. Yanga, Novel poly(phenyleneethynylene)-type conjugated polymers containing diketopyrrolopyrrole or triphenylpyrazoline units in the main chain, synthesis, characterization and photophysical properties, Polym. Int., 58(2009), 665-673.#6. A. R. Rabindranath, K. Zhang, B. Tieke, Purple red and luminescent polyiminoarylenes containing the 1,4-diketo-3,6-diphenylpyrrolo[3,4-c] pyrrole (DPP) chromo-phore, Polym., 50(2009), 1637-1644.#7. G. M. Fischer, A. Zumbusch, E. Daltrozzo, Near-infrared dyes and fluorophores based on diketopyrrolopyrroles, Angew. Chem. Int., 46(2007), 3750-3753.#8. B. Walker, A. X. D. Dang, P. Zalar, J. Hwaseo, A. Garcia, M. Tantiwiwat, T-Q Nguyen, Nanoscale phase separation and high photovoltaic efficiency in solution-processed, small-molecule bulk heterojunction solar Cells., Adv. Mater., 19(2009), 1-7.#9. M. Hidenori, N. Tomiya, T. Murohoshy, Process of producing of dichlorodiketopyrrolopyrrole pigment of alpha modification produced by the process and coloring composition using the same, US Pat. 7431762, 2008.#10. T. Sato, T. Omura, Y. Takabatake, Y. Airyoshi, Alpha-diketopyrrolopyrrolepigments, coloring composi-tion containing the same and red film, US Pat. 0009214, 2010.#11. Zh. Hao, Crystal modification of diketopyrrolo-pyrrole pigments, US Pat. 559168, 1997.#12. T. Ruch, Crystal modification of diketopyrrolo-pyrrole pigments, US Pat. 5171575, 1999.#13. G. Mehretter, H. J. M., Carstenplueg, Finishing treatment of pigments in ionic liquids, US Pat. 0215007, 2007.#14. T. Beyerleina, B. T. S. Forero-Lengerb, W. Bruttingb, Red electroluminescence from a 1, 4-diketopyrrolo [3,4-c] pyrrole (DPP)-based conjugated polymer, Synth. Met., 130(2002), 115-119.#15. R. D. Rogers, Multi functional Ionic liquid components for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional and energetic ingredients, US Pat. 0093469 A1, 2007.#16. M. Farlane, Nitrile functionalized methimazole-based ionic liquids, J. Org. Chem., 75(2010), 8376-8382.#17. R. Seddoen, Ionic liquids for clean technology, J. Chem. Technol. Biotechnol. 68(1997), 351-356.#18. T. Yamagata, J. Kuwabara, T. Kanbara, Synthesis of highly fluorescent diketopyrrolopyrrole derivative and two-step response of fluorescence to acid, Tetrahedron Lett., 51(2010), 1596-1599.

Article's file
Page view: 2953
Article's download quantity : 836

Article System Login

Prof. Zahra Ranjbar
Dr. Farahnaz Nourmohammadian
Assistant Editor:
Dr. Mozhgan Hosseinnezhad
ISSN (online):
Institute for Color Science and Technology (ICST)

Quick Access
What is your opinion about the manuscript subscription system of PCCC website?
Website Statistics
Page view:2,954
Online Visitors:91