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As an initial step toward this goal, we report the synthesis and comprehensive characterization of a new class of boron\u2010, nitrogen\u2010, and oxygen\u2010doped\n                    <jats:italic>peri<\/jats:italic>\n                    \u2010acenoacenes, termed (2,5,4)\u2010trapeziumene congeners. Analysis of these systems provides chemical descriptors that could guide the rational tailoring of their properties through peripheral doping. The target trapeziumene congeners were obtained via a sequence of Suzuki\u2013Miyaura and Buchwald\u2013Hartwig couplings, followed by directed borylation, giving both phenylborane and borinic derivatives with diverse peripheral doping sequences. Single\u2010crystal X\u2010ray diffraction revealed planar to slightly twisted backbones, with peripheral heteroatomic motifs that modulate \u03c0\u2010conjugation and intermolecular packing. Photophysical studies showed bright fluorescence (\n                    <jats:italic>\u03a6<\/jats:italic>\n                    <jats:sub>F<\/jats:sub>\n                    up to 0.99), narrow Stokes shifts, and structured phosphorescence at 77\u00a0K. Electrochemical analysis demonstrated p\u2010type behavior and a progressive HOMO\u2013LUMO gap widening upon N\u2192O substitution. Theoretical investigations revealed that N\u2192O substitution asymmetrically affects the excited states, blue\u2010shifting fluorescence while red\u2010shifting phosphorescence, through an asymmetric charge stabilization in the S\n                    <jats:sub>1<\/jats:sub>\n                    and T\n                    <jats:sub>1<\/jats:sub>\n                    excited states. This is accompanied by a progressive widening of the T\n                    <jats:sub>1<\/jats:sub>\n                    \u2013T\n                    <jats:sub>2<\/jats:sub>\n                    energy gap.\n                  <\/jats:p>","DOI":"10.1002\/anie.202517114","type":"journal-article","created":{"date-parts":[[2025,9,17]],"date-time":"2025-09-17T06:17:06Z","timestamp":1758089826000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["BN\/BO Doping of\n                    <i>peri<\/i>\n                    \u2010Acenoacenes: Modulating Excited States in Trapeziumene Congeners"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0529-8574","authenticated-orcid":false,"given":"Daniele","family":"Poletto","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  Vienna 1090 Austria"},{"name":"Doctoral School in Chemistry (DoSChem) University of 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