An Efficient Pathway to Synthesize Diketopyrrolopyrrole Pigments in Ionic Liquids

Author(s): Farahnaz Nourmohammadian, S. Shiva Shamekhi.

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 2 , 2013

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The investigation results of an efficient pathway for the synthesis of high-performance 1, 4-diketo-3, 6- diphenyl pyrrolo [3, 4-c] pyrroles pigments using diethyl succinate in ionic liquids ([BMIM][BF4], and [HMIM][BF4]) has been reported. Synthesis of 3, 6-Bis (4-chlorophenyl)-2, 5-dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione using [BMIM][BF4] is more efficient (81% at 30°C) than conventional methods (70% at 105-110°C). 3, 6-Bis (4-bromophenyl)-2, 5- dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione was produced in this approach with 73% yield at 30°C in 8 h reaction time instead of the previously reported (65% yield in 24 h). The production yield of 1, 4-diketo-3, 6-diphenyl pyrrolo [3, 4-c] pyrroles was not highly affected by ionic liquids, and produced in maximum 43% yield.

The crystalline phase, particle sizes and morphologies of the synthesized pigments have also been reported.

Keywords: Crystalline phase, diethyl succinate, diketopyrrolopyrole, pigment, Ionic liquid

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Article Details

Year: 2013
Page: [131 - 138]
Pages: 8
DOI: 10.2174/1570178611310020012
Price: $58

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