Pal, ArnabArnabPalKim, HakjeongHakjeongKimSuresh, ShreeragShreeragSureshWei, Po-HanPo-HanWeiAl-Kabbany, Abdullah MohamedAbdullah MohamedAl-KabbanyChoi, DukhyunDukhyunChoiZONG-HONG LIN2026-03-162026-03-162026-01-2800027863https://www.scopus.com/record/display.uri?eid=2-s2.0-105028969212&origin=resultslisthttps://scholars.lib.ntu.edu.tw/handle/123456789/736346Chirality lies at the heart of chemistry, governing the structure–function relationships of biomolecules, pharmaceuticals, and catalysts. However, rapid and label-free enantioselective analysis remains an enduring challenge due to the intrinsic similarity of enantiomers’ physicochemical properties. Here, we report a contact electrification–based triboelectric sensing platform for the enantioselective recognition of chiral amino acids, achieved by coating CuO nanowires. The approach exploits chirality-dependent interfacial electron transfer, whereby differences in molecular orbital alignment and work function between enantiomers generate distinct electronic signatures during controlled contact–separation with acetone. Kelvin probe force microscopy, ultraviolet photoelectron spectroscopy, and density functional theory calculations reveal that subtle differences in side-chain geometry modulate nanoscale surface potentials and electron cloud overlap, leading to quantifiable shifts in charge transfer efficiency. The method achieves millisecond-scale discrimination across charged, polar uncharged, and sulfur-containing amino acids, with orthogonal evidence from molecule specific enantioselective contact-electrocatalytic degradation of methyl orange. By transducing stereochemical information directly into measurable electrical outputs, this work demonstrates a mechanistically grounded chemical sensing paradigm, offering a versatile platform for pharmaceutical quality control and biomolecular diagnostics.truejournal article10.1021/jacs.5c156082-s2.0-105028969212