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Harnessing geometrical and electrical changes in response to multiple external stimuli on the molecular level to modulate properties remains a fundamental challenge. Herein, the reversible formation of the aggregates of <jats:sc>l<\/jats:sc>\u2010tyrosine <jats:italic>E<\/jats:italic>\u2010azobenzene\u2010tetracarboxamide (<jats:bold><jats:italic>E<\/jats:italic><\/jats:bold>\u2010<jats:bold>ABT<\/jats:bold>) is shown to be finely controlled by light, solvent, or chemical additives. The resulting products differ not only in their overall morphology and supramolecular interactions, but also in their intrinsic chirality, that is, depending on the conditions applied, self\u2010assembly yields chiral columns or \u03c0\u2010stacked \u201cachiral\u201d oligomers. This report shows the potential of rational monomer design to achieve controlled self\u2010assembly by stimuli of choice and paves the way toward the use of multi\u2010responsive, sterically hindered azo\u2010benzene aggregates in materials chemistry and nanotechnology.<\/jats:p>","DOI":"10.1002\/smtd.202301681","type":"journal-article","created":{"date-parts":[[2024,2,12]],"date-time":"2024-02-12T10:22:48Z","timestamp":1707733368000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Chiral versus Achiral Assemblies in Multi\u2010Stimuli Responsive Supramolecular Polymerization of Tetra\u2010Substituted Azobenzene Dye"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0107-3880","authenticated-orcid":false,"given":"Miroslava","family":"\u010conkov\u00e1","sequence":"first","affiliation":[{"name":"Faculty of Chemistry Adam Mickiewicz University  Uniwersytetu Pozna\u0144skiego 8 Pozna\u0144 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