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Here, we implement the tolane\u2010perfluorotolane interaction as base pair replacement in DNA. Tolane (THH) and perfluorotolane (TFF) moieties were connected to acyclic backbone units, comprising glycol nucleic acid (GNA) or butyl nucleic acid (BuNA) building blocks, that were incorporated via phosphoramidite chemistry at opposite positions in a DNA duplex. Thermodynamic analyses by UV thermal melting revealed a compelling stabilization by THH\/TFF heteropairs only when connected to the BuNA backbone, but not with the shorter GNA linker. Detailed NMR studies confirmed the preference of the BuNA backbone for enhanced polar \u03c0\u2010stacking. This work defines how orthogonal supramolecular interactions can be tailored by small constitutional changes in the DNA backbone, and it inspires future studies of arene\u2010fluoroarene\u2010programmed assembly of DNA.<\/jats:p>","DOI":"10.1002\/anie.202214456","type":"journal-article","created":{"date-parts":[[2022,11,7]],"date-time":"2022-11-07T22:37:01Z","timestamp":1667860621000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Tailored Tolane\u2010Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA"],"prefix":"10.1002","volume":"62","author":[{"given":"Hermann","family":"Neitz","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry University of W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irene","family":"Bessi","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry 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