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In the present work, the exploitation of the <jats:italic>Z\/E<\/jats:italic> (geometrical) isomerism of squaramide (SQ) units to produce various self\u2010assembled isoforms and complex supramolecular polymerization pathways in methylcyclohexane\/CHCl<jats:sub>3<\/jats:sub> mixtures is reported for the first time. This is achieved by using a new bissquaramidic macrocycle (<jats:bold>MSq<\/jats:bold>) that self\u2010assembles into two markedly different thermodynamic aggregates, <jats:bold>AggA<\/jats:bold> (discrete cyclic structures) and <jats:bold>AggB<\/jats:bold> (fibrillar structures), depending on the solvent composition and concentration. Remarkably, UV\u2013vis, <jats:sup>1<\/jats:sup>H NMR, and FT\u2010IR experiments together with quantum\u2010chemical calculations indicate that these two distinct aggregates are formed via two different hydrogen bonding patterns (side\u2010to\u2010side in <jats:bold>AggA<\/jats:bold> and head\u2010to\u2010tail in <jats:bold>AggB<\/jats:bold>) due to different conformations in the SQ units (<jats:italic>Z,E<\/jats:italic> in <jats:bold>AggA<\/jats:bold> and <jats:italic>Z,Z<\/jats:italic> in <jats:bold>AggB<\/jats:bold>). The ability of <jats:bold>MSq<\/jats:bold> to supramolecularly polymerize into two distinct aggregates is utilized to induce the kinetic\u2010to\u2010thermodynamic transformation from <jats:bold>AggA<\/jats:bold> to <jats:bold>AggB<\/jats:bold>, which occurs via an on\u2010pathway mechanism. It is believed that this system provides new insights for the design of potential supramolecular polymorphic materials by using squaramide units.<\/jats:p>","DOI":"10.1002\/smll.202006133","type":"journal-article","created":{"date-parts":[[2021,1,15]],"date-time":"2021-01-15T23:10:49Z","timestamp":1610752249000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Influence of the <i>Z<\/i>\/<i>E<\/i> Isomerism on the Pathway Complexity of a Squaramide\u2010Based Macrocycle"],"prefix":"10.1002","volume":"17","author":[{"given":"Francisca","family":"Orvay","sequence":"first","affiliation":[{"name":"Department of Chemistry University of the Balearic Islands  Cra. 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