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Here, we investigate this interplay for two series of 1,4\u2010benzene bisamides with symmetric and asymmetric peripheral substitution. We elucidated the crystal structures, determined the nano\u2010object morphologies and derived the wetting behaviour of the preferentially exposed surfaces. The crystal structures were solved by combining single\u2010crystal and powder X\u2010ray diffraction, solid\u2010state NMR spectroscopy and computational modelling. Bulky side groups, here t\u2010butyl groups, serve as a structure\u2010directing 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\u2010assemble the benzene bisamides into a second packing pattern which leads to ribbon\u2010like nano\u2010objects. 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\u2010objects.<\/jats:p>","DOI":"10.1002\/cphc.202100597","type":"journal-article","created":{"date-parts":[[2021,10,13]],"date-time":"2021-10-13T17:10:07Z","timestamp":1634145007000},"page":"2585-2593","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Crystal Engineering of Supramolecular 1,4\u2010Benzene Bisamides by Side\u2010Chain Modification \u2013 Towards Tuneable Anisotropic Morphologies and Surfaces"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3568-5129","authenticated-orcid":false,"given":"Kasper P.","family":"van der Zwan","sequence":"first","affiliation":[{"name":"Inorganic Chemistry III and North Bavarian NMR Center University of Bayreuth  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