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Herein, we describe membrane\u2010targeting molecular devices based on the triplexes of poly T\n                    <jats:italic>acyclic<\/jats:italic>\n                    L\u2010threoninol nucleic acid (L\u2010\n                    <jats:italic>a<\/jats:italic>\n                    TNA) tethered site\u2010specifically to cholesterol and poly A DNA. The L\u2010\n                    <jats:italic>a<\/jats:italic>\n                    TNA was linked to cholesterol in two different orientations. The membrane\u2010binding properties differed depending on the orientation at the cholesterol linkage. One triplex adhered to giant unilamellar vesicles and the other penetrated these vesicles. When the membrane\u2010penetrating triplex was formed with a photoresponsive DNA, photoresponsive signal transduction into giant unilamellar vesicles was enabled. These membrane\u2010targeting molecular devices have potential as biosensors, artificial organs, and molecular robots and in chemical artificial intelligence. Moreover, this strategy for post\u2010modification of the propargyl\u2010L\u2010\n                    <jats:italic>a<\/jats:italic>\n                    TNA unit will enable further functionalization of L\u2010\n                    <jats:italic>a<\/jats:italic>\n                    TNA and other acyclic XNAs.\n                  <\/jats:p>","DOI":"10.1002\/anie.202516095","type":"journal-article","created":{"date-parts":[[2025,11,27]],"date-time":"2025-11-27T12:03:13Z","timestamp":1764244993000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Membrane\u2010Penetrating Molecular Device Based on a Triplex Containing Acyclic L\u2010Threoninol Nucleic Acid Functionalized with Cholesterol"],"prefix":"10.1002","volume":"65","author":[{"given":"Kaifu","family":"Liu","sequence":"first","affiliation":[{"name":"Department of Biomolecular Engineering Graduate School of Engineering Nagoya University  Furo\u2010cho, 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