<i>N</i>,<i>N</i>′-(1,4-Phenylene)bis(4-chlorobutanamide)

Cuzan, Olesea; Shova, Sergiu; Turta, Constantin; Mangalagiu, Ionel I.

doi:10.1107/s1600536812001341

Cited by 1 publication

(6 citation statements)

References 7 publications

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“…For series 1 , one molecule binds to two neighbouring molecules with two hydrogen bonds each, one as a donor and one as an acceptor. This corresponds to the supramolecular synthon observed in references [30–33] Thereby the molecules form a ribbon along the crystallographic a ‐axis. Along the b ‐axis, the molecules assemble via van der Waals interactions by the interlocking side chains.…”

Section: Resultsmentioning

confidence: 67%

“…Whereas, Mangalugui et al. published the crystal structure of a bisamide with a slim 3‐chloro‐propyl side chain, which assembles in the parallel packing of series 1 [32] . A bisamide with cyclohexane side groups is also slim enough to crystallise in the packing type of series 1 [17] .…”

Section: Resultsmentioning

confidence: 99%

“…Either one molecule forms hydrogen bonds to two [30–33] or to four [34–37] other molecules. In the first case a linear arrangement of the molecules arises that features a packing with strong interactions in one dimension [30–33] . This implies the growth of an object with one preferred growth rate and an anisotropic morphology.…”

Section: Introductionmentioning

confidence: 99%

“…Up to now, two supramolecular synthons have been observed. Either one molecule forms hydrogen bonds to two[ 30 , 31 , 32 , 33 ] or to four[ 34 , 35 , 36 , 37 ] other molecules. In the first case a linear arrangement of the molecules arises that features a packing with strong interactions in one dimension.…”

Section: Introductionmentioning

confidence: 99%

“…In the first case a linear arrangement of the molecules arises that features a packing with strong interactions in one dimension. [ 30 , 31 , 32 , 33 ] This implies the growth of an object with one preferred growth rate and an anisotropic morphology. In the second case, the twisted arrangement of the five molecules involved in the supramolecular synthon induces packings with strong interactions in two dimensions.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Engineering of Supramolecular 1,4‐Benzene Bisamides by Side‐Chain Modification – Towards Tuneable Anisotropic Morphologies and Surfaces

et al. 2021

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Benzene bisamides are promising building blocks for supramolecular nano‐objects. Their functionality depends on morphology and surface properties. However, a direct link between surface properties and molecular structure itself is missing for this material class. Here, we investigate this interplay for two series of 1,4‐benzene bisamides with symmetric and asymmetric peripheral substitution. We elucidated the crystal structures, determined the nano‐object morphologies and derived the wetting behaviour of the preferentially exposed surfaces. The crystal structures were solved by combining single‐crystal and powder X‐ray diffraction, solid‐state NMR spectroscopy and computational modelling. Bulky side groups, here t‐butyl groups, serve as a structure‐directing motif into a packing pattern, which favours the formation of thin platelets. The use of slim peripheral groups on both sides, in our case linear perfluorinated, alkyl chains, self‐assemble the benzene bisamides into a second packing pattern which leads to ribbon‐like nano‐objects. For both packing types, the preferentially exposed surfaces consist of the ends of the peripheral groups. Asymmetric substitution with bulky and slim groups leads to an ordered alternating arrangement of the groups exposed to the surface. This allows the hydrophobicity of the surfaces to be gradually altered. We thus identified two leitmotifs for molecular packings of benzene bisamides providing the missing link between the molecular structure, the anisotropic morphologies and adjustable surface properties of the supramolecular nano‐objects.

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Section: Resultsmentioning

confidence: 67%

Section: Resultsmentioning

confidence: 99%