Influence of fluorine side-group substitution on the crystal structure formation of benzene-1,3,5-trisamides

Zehe, Christoph S.; Schmidt, Marko; Siegel, Renée; Kreger, Klaus; Daebel, Venita; Ganzleben, Sandra; Schmidt, Hans‐Werner; Senker, Jürgen

doi:10.1039/c4ce01077a

Cited by 10 publications

(9 citation statements)

References 71 publications

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“…In line with the structural considerations, p amounts to 12 D and 11 D for 1 and 2 , respectively, and to 6.5 D for 4 . For the latter, the p value is reduced further because of the anti alignment of the C−F and C=O bonds, which is induced by intramolecular NH⋅⋅⋅F hydrogen bonds (Figure a, b and Figure S4 b) . In the case of 3 , we expect a value close to the one derived for 2 as their mean torsion angles are similar.…”

Section: Figurementioning

confidence: 98%

Mesoscale Polarization by Geometric Frustration in Columnar Supramolecular Crystals

et al. 2017

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Columnar supramolecular phases with polarization along the columnar axis have potential for the development of ultrahigh‐density memories as every single column might function as a memory element. By investigating structure and disorder for four columnar benzene‐1,3,5‐trisamides by total X‐ray scattering and DFT calculations, we demonstrate that the column orientation, and thus the columnar dipole moment, is receptive to geometric frustration if the columns aggregate in a hexagonal rod packing. The frustration suppresses conventional antiferroelectric order and heightens the sensitivity towards collective intercolumnar packing effects. The latter finding allows for the building up of mesoscale domains with spontaneous polarization. Our results suggest how the complex interplay between steric and electrostatic interactions is influenced by a straightforward chemical design of the molecular synthons to create spontaneous polarization and to adjust mesoscale domain size.

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Section: Figurementioning

confidence: 98%

Mesoscale Polarization by Geometric Frustration in Columnar Supramolecular Crystals

et al. 2017

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“…Subsequently one solution was selected that was favoured by multiple metrics. In a similar vein, the crystal structure of a benzene-1,3,5-trisamide with fluorine-substituted t-butyl groups was solved from PXRD data [339]. Indexing of the diffractogram showed Z = 4, while the NMR data indicated Z' >= 2, helping to identify compatible space groups.…”

Section: 7mentioning

confidence: 99%

NMR crystallography of molecular organics

Hodgkinson

2020

Progress in Nuclear Magnetic Resonance Spectroscopy

110

112

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“…Im Einklang mit den strukturellen Überlegungen, beträgt p 12 D und 11 D bei 1 und 2 und 6.5 D bei 4 . Der geringere Wert für 4 resultiert aus der antiparallelen Ausrichtung der C‐F‐ und C=O‐Bindungen, welche durch intramolekulare NH⋅⋅⋅F‐Wasserstoffbrücken induziert wird (Abbildungen a,b und S4b, SI) . Im Falle von 3 erwarten wir einen ähnlichen Wert für 2 , da ihre mittleren Torsionswinkel vergleichbar sind.…”

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Polarisation auf der Mesoskala durch geometrische Frustration in kolumnaren supramolekularen Kristallen

Zehe

Hill²,

Funnell

et al. 2017

Angewandte Chemie

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Kolumnare supramolekulare Phasen, die eine Polarisation entlang der Kolumnenachse aufweisen, haben das Potential zur Entwicklung von Datenspeichern mit ultrahoher Dichte, da jede einzelne Kolumne als Speicherelement fungieren kann. Wir zeigen anhand von Untersuchungen der Struktur und Unordnung von vier kolumnaren 1,3,5-Benzoltrisamiden mittels totaler Rçntgenstreuung und DFT-Rechnungen, dass die Kolumnenorientierung und damit das kolumnare Dipolmoment empfindlich auf geometrische Frustration ist, sofern die Kolumnen in hexagonalen Stabpackungen aggregieren. Die Frustration unterdrückt die konventionelle antiferroelektrische Ordnung und erhçht die Sensitivität für kollektive interkolumnare Packungseffekte. Dieser Befund erlaubt es, Domänen auf der Mesoskala zu erzeugen, die eine spontane Polarisation aufweisen. Unsere Ergebnisse zeigen auf, wie das komplexe Zusammenspiel von sterischen und elektrostatischen Wechselwirkungen durch ein einfaches Design der molekularen Synthone beeinflusst wird, um spontane Polarisation zu erzeugen und die Grçße der mesoskopischen Domänen einzustellen.

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Influence of fluorine side-group substitution on the crystal structure formation of benzene-1,3,5-trisamides

Abstract: The crystal structure of 1,3,5-tris(2-fluoro-2-methylpropionylamino)benzene was solved by combining powder X-ray diffraction, solid-state NMR spectroscopy and quantum chemical calculations.

Cited by 10 publications

References 71 publications

Mesoscale Polarization by Geometric Frustration in Columnar Supramolecular Crystals

Mesoscale Polarization by Geometric Frustration in Columnar Supramolecular Crystals

NMR crystallography of molecular organics

Polarisation auf der Mesoskala durch geometrische Frustration in kolumnaren supramolekularen Kristallen

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