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Herein, we report a strategy for reshaping self\u2010assembled chiral nanomaterials mediated by a [2+2] cycloaddition reaction. Amino acids grafted with large \u03c0\u2010conjugated systems are employed as the primary building blocks, into which the electron\u2010deficient tetracyanoquinodimethane (TCNQ) and ethynylaniline (EDA) are orthogonally introduced. These components form ternary co\u2010assemblies through charge\u2010transfer interactions and hydrogen bonding, respectively. In the aggregated phase, TCNQ and EDA undergo an efficient, spontaneous [2+2] cycloaddition reaction to afford a nonplanar adduct. This reaction is accompanied by the formation of macroscopic helices with high phase purity. Owing to the high efficiency of this reaction, such chiral architectures can be generated in situ by post\u2010addition of the third component into preassembled binary systems. This topochemical synthetic strategy compensates for the narcissistic assembly by directly using the as\u2010synthesized adduct, and remarkably enhances chiral induction as well as near\u2010infrared chiroptical properties. In contrast to widely reported template effects, this system exhibits a distinctive cooperative behavior, wherein the insoluble reaction products undergo preferential and directional organization within the aggregates rather than remaining at original formation sites.<\/jats:p>","DOI":"10.1002\/anie.1508190","type":"journal-article","created":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T12:46:45Z","timestamp":1785415605000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Reshaping Chiral Self\u2010Assemblies Through Alkyne\u2010Involved Click Chemistry"],"prefix":"10.1002","volume":"65","author":[{"given":"Zhuoer","family":"Wang","sequence":"first","affiliation":[{"name":"Key Laboratory of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering Shandong University  Jinan People's Republic of 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