Electron diffraction and crystal engineering of Pigment Red 5, C30H31ClN4O7S.
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| Title: | Electron diffraction and crystal engineering of Pigment Red 5, C |
|---|---|
| Authors: | Reibeling, Sylvia1 (AUTHOR), Gorelik, Tatiana E.2,3 (AUTHOR) t.gorelik@fz-juelich.de, Haussühl, Eiken4 (AUTHOR), Liebisch, Nick1 (AUTHOR), Piepenbring, Martin U.1 (AUTHOR) piepenbring@chemie.uni-frankfurt.de |
| Source: | CrystEngComm. 6/15/2026, Vol. 28 Issue 23, p3558-3578. 21p. |
| Subjects: | Electron diffraction, Solid solutions, Organic dyes, Crystal lattices, X-ray crystallography, Computational chemistry |
| Abstract: | Pigment Red 5 (P.R.5) is an industrial organic hydrazone pigment with non-optimal application properties. In its application media – paints and printing inks – the pigment is not dissolved, but finely dispersed; hence, the crystal structure is maintained and has a strong effect on the properties. Hitherto, the crystal structure of P.R.5 has not been known, because the pronounced insolubility in water and in common organic solvents hampers the growth of single crystals for X-ray analysis. Since structure determination from powder data failed as well, the structure was determined by 3-dimensional electron diffraction (3D-ED). P.R.5 crystallises in the triclinic space group P1̄ (Z = 2), with layers of largely planar molecules. The structure was later confirmed by single-crystal X-ray analysis of a tiny crystal. The structure contains a void of about 36 Å3 between the molecules—a feature unprecedented in any known commercial organic pigment, as such voids deteriorate the packing efficiency, the lattice energy, and the application properties. To address these drawbacks, crystal engineering strategies were applied. First, lattice-energy minimisations guided the selection of potential derivatives and solid solutions. Several promising solid solutions were then synthesised and analysed by X-ray powder diffraction and single crystal analysis, and, indeed, according to the lattice-energy minimisations, the void could be filled. [ABSTRACT FROM AUTHOR] |
| Copyright of CrystEngComm is the property of Royal Society of Chemistry and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 194547103 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Electron diffraction and crystal engineering of Pigment Red 5, C<subscript>30</subscript>H<subscript>31</subscript>ClN<subscript>4</subscript>O<subscript>7</subscript>S. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Reibeling%2C+Sylvia%22">Reibeling, Sylvia</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Gorelik%2C+Tatiana+E%2E%22">Gorelik, Tatiana E.</searchLink><relatesTo>2,3</relatesTo> (AUTHOR)<i> t.gorelik@fz-juelich.de</i><br /><searchLink fieldCode="AR" term="%22Haussühl%2C+Eiken%22">Haussühl, Eiken</searchLink><relatesTo>4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Liebisch%2C+Nick%22">Liebisch, Nick</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Piepenbring%2C+Martin+U%2E%22">Piepenbring, Martin U.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> piepenbring@chemie.uni-frankfurt.de</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22CrystEngComm%22">CrystEngComm</searchLink>. 6/15/2026, Vol. 28 Issue 23, p3558-3578. 21p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Electron+diffraction%22">Electron diffraction</searchLink><br /><searchLink fieldCode="DE" term="%22Solid+solutions%22">Solid solutions</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+dyes%22">Organic dyes</searchLink><br /><searchLink fieldCode="DE" term="%22Crystal+lattices%22">Crystal lattices</searchLink><br /><searchLink fieldCode="DE" term="%22X-ray+crystallography%22">X-ray crystallography</searchLink><br /><searchLink fieldCode="DE" term="%22Computational+chemistry%22">Computational chemistry</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Pigment Red 5 (P.R.5) is an industrial organic hydrazone pigment with non-optimal application properties. In its application media – paints and printing inks – the pigment is not dissolved, but finely dispersed; hence, the crystal structure is maintained and has a strong effect on the properties. Hitherto, the crystal structure of P.R.5 has not been known, because the pronounced insolubility in water and in common organic solvents hampers the growth of single crystals for X-ray analysis. Since structure determination from powder data failed as well, the structure was determined by 3-dimensional electron diffraction (3D-ED). P.R.5 crystallises in the triclinic space group P1̄ (Z = 2), with layers of largely planar molecules. The structure was later confirmed by single-crystal X-ray analysis of a tiny crystal. The structure contains a void of about 36 Å3 between the molecules—a feature unprecedented in any known commercial organic pigment, as such voids deteriorate the packing efficiency, the lattice energy, and the application properties. To address these drawbacks, crystal engineering strategies were applied. First, lattice-energy minimisations guided the selection of potential derivatives and solid solutions. Several promising solid solutions were then synthesised and analysed by X-ray powder diffraction and single crystal analysis, and, indeed, according to the lattice-energy minimisations, the void could be filled. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of CrystEngComm is the property of Royal Society of Chemistry and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1039/d6ce00140h Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 21 StartPage: 3558 Subjects: – SubjectFull: Electron diffraction Type: general – SubjectFull: Solid solutions Type: general – SubjectFull: Organic dyes Type: general – SubjectFull: Crystal lattices Type: general – SubjectFull: X-ray crystallography Type: general – SubjectFull: Computational chemistry Type: general Titles: – TitleFull: Electron diffraction and crystal engineering of Pigment Red 5, C30H31ClN4O7S. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Reibeling, Sylvia – PersonEntity: Name: NameFull: Gorelik, Tatiana E. – PersonEntity: Name: NameFull: Haussühl, Eiken – PersonEntity: Name: NameFull: Liebisch, Nick – PersonEntity: Name: NameFull: Piepenbring, Martin U. IsPartOfRelationships: – BibEntity: Dates: – D: 15 M: 06 Text: 6/15/2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 14668033 Numbering: – Type: volume Value: 28 – Type: issue Value: 23 Titles: – TitleFull: CrystEngComm Type: main |
| ResultId | 1 |
