ChemInform Abstract: Synthesis and Properties of 1,4‐Diketo‐pyrrolo(3,4‐C)pyrroles

Iqbal, Abul F. M.; Jost, Micha; Kirchmayr, R.; Pfenninger, J.; Rochat, Alain Claude; Wallquist, O.

doi:10.1002/chin.198911158

Cited by 35 publications

(43 citation statements)

References 1 publication

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“…Diketopyrrolopyrrole (abbreviated to DPP) pigments are industrially important red pigments based on the novel diketopyrrolopyrrole chromophore [2]. DPPs are also used as colorants for imaging areas as well as a color filter for LCD applications.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-1,4-dione, C30H20N2O2

Mizuguchi¹,

Miyazaki²

2002

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was obtained from CIBA Specialty Chemicals. The sample was purified by sublimation at about 620 K, using a two-zone furnace [1]. After 60 h, a number of red platelet crystals were obtained. Experimental detailsThe quality of the crystal studied was not sufficiently high, so that only 45% of the measured reflections could be considered as observed (/obs > 3a(/ 0 bs))· This is also reflected in the final relative high Λ-values. DiscussionDiketopyrrolopyrrole (abbreviated to DPP) pigments are industrially important red pigments based on the novel diketopyrrolopyrrole chromophore [2]. DPPs are also used as colorants for imaging areas as well as a color filter for LCD applications. Up to now, five DPP-derivatives are on the market and most of their structures have already been analyzed [3][4][5][6]. The title compound (BP-DPP) is characterized by an extremely large bathochromic shift upon crystallization as compared with other DPP analogues.The present structure analysis has therefore been carried out in order to clarify the electronic structure of BP-DPP. As shown in the figure, the molecule is deformed as characterized by molecular symmetry of Ci. The two phenyl rings on each side of the heterocyclic ring system are twisted asymmetrically in opposite directions. In addition, the heterocyclic ring system is not entirely planar, but is folded in the middle with a dihedral angle of 175.7°. Due to this deformed structure, a dipole moment of about 0.18 D appears perpendicular to the molecular plane. The molecules are arranged in a fashion "bricks in a brick wall", just like J-aggregates in cyanine dyestuffs [7]. There are two kinds of stacking columns: one is composed of the molecules with an upward dipole moment while the neighboring column comprises the molecules with a downward dipole moment. The polar molecules are stacked pairwise so as to reduce the electrostatic energy. On the other hand, on the molecular plane along the a axis, there are chains of intermolecular hydrogen bonds between the NH group of one molecule and the O atom of the neighboring one. This forms a two-dimensional hydrogen bond network as found in all DPP pigments [3][4][5][6]. Details of the correlation between the crystal and electronic structures are given in references [8,9].

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-1,4-dione, C30H20N2O2

Mizuguchi¹,

Miyazaki²

2002

Zeitschrift Für Kristallographie - New Crystal Structures

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“…29 DPPcontaining materials are bright and strongly fluorescent with exceptional photochemical, mechanical, and thermal stability and are therefore used in industrial applications as highperformance pigments in paints, plastics, and inks. 30 DPP-based molecular materials, however, are not soluble in most common organic solvents due to the concurrent strong H-bonding and π-π intermolecular interactions in the solid state. 31 Soluble derivatives, however, can be made by attaching solubilizing groups including ionic groups, 32 charged, 33 or neutral long alkyl chains, 34,35 and organic protecting groups such as t-Boc 36 on the 3,4-positions (i.e., the lactam N atoms) and/or on the 2,5-positions of the DPP moiety.…”

Section: Introductionmentioning

confidence: 99%

A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells

Tamayo¹,

Walker²,

Nguyen³

2008

J. Phys. Chem. C

359

296

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We synthesized a low band gap, solution processable oligothiophene derivative functionalized with a diketopyrrolopyrrole core, which is a highly absorbing chromophoric group. This design leads to optical absorption that extends to 720 nm in solution and to 820 nm in the film. Cyclic voltammetry shows quasireversible oxidation and reduction processes. Bulk heterojunction solar cells using [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as the electron acceptor were fabricated. The power conversion efficiencies (PCEs) depend on the donor-acceptor ratio. A 70:30 donor/acceptor by weight mixture provided a PCE of 2.3% under simulated AM 1.5 solar irradiation of 100 mW/cm 2 . To date, this is the highest efficiency reported for small molecule-based solution processed bulk heterojunction solar cells.

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“…Pigment Red 254, which is based on DPP (Diketopyrrolo-pyrrole) and was first synthesized by Ciba-Geigy, has mainly found use in paints and inks as well as LCD color filters owing to its excellent thermal stability and bright red shade. [6][7][8][9] DPP derivatives are known for their poor solubility in most organic solvent due to their tendency to form strong - interactions and intermolecular hydrogen bonds. Much effort has focused on functionalizing them to improve their solubility.…”

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confidence: 99%

Synthesis and Thermal Stability of Solvent Soluble Dyes Based on Dimerized Diketo-pyrrolo-pyrrole Pigment

Lee¹,

Kim²,

Yoo³

et al. 2014

Bulletin of the Korean Chemical Society

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ChemInform Abstract: Synthesis and Properties of 1,4‐Diketo‐pyrrolo(3,4‐C)pyrroles

Abstract: ChemInform Abstract (lecture given at the XIIIth European Colloquium on Heterocyclic Chemistry, University of Fribourg, Switzerland, September 26-28, 1988).

Cited by 35 publications

References 1 publication

Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-1,4-dione, C30H20N2O2

Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-1,4-dione, C30H20N2O2

A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells

Synthesis and Thermal Stability of Solvent Soluble Dyes Based on Dimerized Diketo-pyrrolo-pyrrole Pigment

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