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Herein, we report the first synthesis of hexa\u2010arylborazines that, bearing\n                    <jats:italic>ortho<\/jats:italic>\n                    \u2010substituted aryl moieties, extend three\u2010dimensionally. Using a one\u2010pot protocol, we first form an electrophilic chloroborazole and then react it with an aryl lithium (ArLi). By selecting the appropriate\n                    <jats:italic>ortho<\/jats:italic>\n                    \u2010substituent, we can guide the ArLi to add to the BN\u2010core in a specific way, ultimately controlling the stereochemical outcome of the three\u2010substitution reaction. Rationalization of the stereochemical model through computational analysis allowed us to show that when aryl lithium nucleophiles bearing rigid long\u2010range\n                    <jats:italic>ortho<\/jats:italic>\n                    \u2010substituents are used, i.e., stiff substituents. The\n                    <jats:italic>ortho<\/jats:italic>\n                    \u2010substituent shields its side of the electrophilic B\n                    <jats:sub>3<\/jats:sub>\n                    N\n                    <jats:sub>3<\/jats:sub>\n                    core, biasing the incoming ArLi to add\n                    <jats:italic>anti<\/jats:italic>\n                    at each addition step, forming the final tri\u2010aryl borazine exclusively as\n                    <jats:italic>cc<\/jats:italic>\n                    \u2010isomer. Leveraging this stereoselective approach, prototypical multichromophoric borazine derivatives were prepared, and we showcased how the stereochemical arrangement of these chromophores distinctly influences their redox behavior. This methodology paves the way for previously inaccessible borazines to serve as privileged precursors to transcend the conventional bidimensionality associated with graphenoid systems and pioneer the construction of new forms of three\u2010dimensional C(sp\n                    <jats:sup>2<\/jats:sup>\n                    )\u2010based architectures.\n                  <\/jats:p>","DOI":"10.1002\/anie.202416700","type":"journal-article","created":{"date-parts":[[2024,11,12]],"date-time":"2024-11-12T08:05:43Z","timestamp":1731398743000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Escape from Flatland: Stereoselective Synthesis of Hexa\u2010aryl Borazines and their sp\n                    <sup>2<\/sup>\n                    \u2010Based 3D Architectures"],"prefix":"10.1002","volume":"64","author":[{"given":"Vivek","family":"Chandrakant Wakchaure","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Faculty of Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda Mercedes","family":"Lorenzo\u2010Garc\u00eda","sequence":"additional","affiliation":[{"name":"School of Chemistry Cardiff University, Main Building  Park Place Cardiff CF10 3AT United Kingdom"},{"name":"Department of Pharmaceutical and Chemical Sciences University of Trieste  Via Licio Giorgeri 1 Trieste 34127 Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesco","family":"Fasano","sequence":"additional","affiliation":[{"name":"School of Chemistry Cardiff University, Main Building  Park Place Cardiff CF10 3AT United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martina","family":"Crosta","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Faculty of Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna 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