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Here, we demonstrate the precise control over helical nanostructures through sequence\u2010specific dipeptide\u2010naphthalenediimide (NDI) conjugates. Two enantiomeric pairs of NDI derivatives, bearing either glycyl\u2010L\/D\u2010leucine (Gly\u2010Leu) or L\/D\u2010leucyl\u2010glycine (Leu\u2010Gly) sequences, were assembled in methanol\/water and dimethylformamide\/water mixed solvents. Strikingly, the Gly\u2010Leu\u2010functionalized derivatives (NDI\u2010Gly\u2010Leu) exhibited sequence\u2010dependent chirality expression, forming eccentric twists and helices with significantly amplified chiroptical signals, while the NDI\u2010Leu\u2010Gly did not. We propose the \u201cradius of torsion\u201d to quantitatively describe the helicity of the nanostructures and correlate with their optical activity for the first time. We further revealed the generation of chiral NDI\n                    <jats:sup>\u2022\u2212<\/jats:sup>\n                    radical anions from NDI derivatives, which also showed the sequence\u2010defined assembly effect. These insights deepen the fundamental understanding of peptide\u2010directed chiral self\u2010assembly and open new avenues for designing functional chiral nanomaterials.\n                  <\/jats:p>","DOI":"10.1002\/anie.202518813","type":"journal-article","created":{"date-parts":[[2025,10,7]],"date-time":"2025-10-07T12:30:34Z","timestamp":1759840234000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Eccentrically Twisted and Helical Nanoarchitectonics by Sequence\u2010Defined Peptide\u2010\u03c0 Conjugates"],"prefix":"10.1002","volume":"64","author":[{"given":"Xin","family":"Wen","sequence":"first","affiliation":[{"name":"Key Laboratory of Colloid Interface and Chemical Thermodynamics Institute of Chemistry Chinese Academy of Sciences (CAS)  ZhongGuanCun North First Street 2 Beijing 100190 China"},{"name":"University of Chinese Academy of Sciences  Beijing 100190 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