Structures of 3,6-diphenylpyrrolo[3,4-<i>c</i>]pyrrole-1,4-dione and 2,5-dimethyl-3,6-diphenylpyrrolo[3,4-<i>c</i>]pyrrole-1,4-dione

Mizuguchi, Jin; Grubenmann, Arnold; Wooden, Gary P.; Rihs, G.

doi:10.1107/s0108768192003033

Cited by 76 publications

(78 citation statements)

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“…The value is much shorter than that for standard single bonds between the sp 2 carbon atoms (∼1.50-1.54 Å), suggesting that the C3-C4 bond has partly a double bond nature. [ 80 ] This also applies for the C2-C2' bond located in the center of the molecule (1.42 Å, Figure 2 ).…”

Section: Reviewmentioning

confidence: 99%

“…The smallest distance between the DPP molecules is 3.34 Å. [ 80 ] Similar to DPP 2 , hydrogen bonding and π -π stacking interactions play key roles in the crystal structures of other DPPs containing para and meta substituents at phenyl groups. [ 81 ] The molecular geometry of various DPP pigments is similar as well.…”

Section: Reviewmentioning

confidence: 99%

“…Because the DPP molecules contain two oppositely directed amide groups, they arrange into infi nite ribbons along the crystal 110 direction (Figure 3 a). [ 80 ] The π -π interactions act perpendicularly to the chromophore plane of DPP 2 , which causes the formation of infi nite columns along the crystal aaxis (Figure 3 b). The smallest distance between the DPP molecules is 3.34 Å.…”

Section: Reviewmentioning

confidence: 99%

“…Crystal structure of DPP 2 (distances in Å). [ 80 ] REVIEW have a noticeable infl uence on the photophysical properties of DPPs. Figure 4 shows the UV-vis spectra of DPP 2 in the solid state and in the solution in dimethyl sulfoxide (DMSO).…”

Section: Reviewmentioning

confidence: 99%

“…[ 80 ] Because of the low solubility of the pigment, the crystallization process was performed through vapor deposition from the gas phase. DPP 2 crystallizes in the triclinic system ( 1 P point group).…”

Section: N -Unsubstituted Dppsmentioning

confidence: 99%

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Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Grzybowski

Gryko

2015

Advanced Optical Materials

330

293

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First reported by Farnum as much as 40 years ago, diketopyrrolopyrroles (2,5‐dihydropyrrolo[4,3‐c]pyrrolo‐1,4‐diones) are currently one of the most widely used dyes, with applications that span high‐quality pigments, field‐effect transistors, bulk‐heterojunction solar cells, dye‐sensitized solar cells, and fluorescence imaging. Due to the breadth of their utility, there have been several focused reviews on this topic since 1988. Considering the growing importance of these dyes, this review describes the overall progress made in four decades in both synthesis and the elucidation of their reactivity, and offers a critical comparison of various methods reported in the literature. The relationship between their structure and optical properties is also reviewed in detail. The extension of diketopyrrolopyrroles' chromophore leads to a significant change in both linear and nonlinear optical properties. A very strong bathochromic shift in the absorption and an increase in the two‐photon absorption cross‐section are typical for these analogues. Straightforward synthesis combined with good stability and a near‐unity fluorescence quantum yield ensures that diketopyrrolopyrroles will continue to attract attention for years to come. The goal of this review is to systematize knowledge on these dyes, enabling their use in more real‐world applications.

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Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

Section: N -Unsubstituted Dppsmentioning

confidence: 99%

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Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Grzybowski

Gryko

2015

Advanced Optical Materials

330

293

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New deeply coloured and fluorescent polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole units in the main chain

Lange

Tieke²

1999

Macromol. Chem. Phys.

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SUMMARY: New deeply coloured and fluorescent copolyesters and -urethanes with 1,4-dioxo-3,6-diphenylpyrrolo [3,4-c]pyrrole (DPP) units in the main chain were prepared. The chromophoric units are incorporated in the backbone via their N-alkylated lactam groups. The DPP-containing monomer 1,4-dioxo-2,5-bis(6-hydroxyhexyl)-3,6-diphenylpyrrolo[3,4-c]pyrrole (2) was obtained by N-alkylation of 1,4-dioxo-3,6-diphenylpyrrolo [3,4-c]pyrrole (1) with 6-chlorohexanol. Copolyesters were prepared by (a) solution polycondensation of mixtures of 2 and 1,12-dodecanediol with terephthaloyl chloride and (b) melt polycondensation of the diol mixture with dimethyl terephthalate using tetrabutoxytitanium as catalyst. Copolyurethanes were prepared by polyaddition of mixtures of 2 and 1,12-dodecanediol with hexamethylene diisocyanate. The copolyesters are readily soluble in common organic solvents, while the copolyurethanes are only soluble in rather exotic solvents such as p-cresol. Polymer solutions are yellow to orange with optical absorption maximum at 470 nm and fluorescence maximum at 520 nm, the Stokes-shift being about 50 nm. All copolymers are partially crystalline, the crystallinity decreasing with increasing DPP content. Possible origins for the influence of the DPP content on the crystallinity of the polymers are discussed. The thermal stability of the copolyesters is independent of the DPP content, the decomposition temperature being about 646 K. The limit of thermal stability of the copolyurethanes is about 600 K and increases slightly with DPP content.

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Diketopyrrolopyrrole (DPP) Pigments

Wallquist

Lenz

2009

High Performance Pigments

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Structures of 3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione and 2,5-dimethyl-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione

Cited by 76 publications

References 0 publications

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

New deeply coloured and fluorescent polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole units in the main chain

Diketopyrrolopyrrole (DPP) Pigments

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