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However, the synthesis of structurally diverse architectures, especially discrete bilayer systems, remains challenging. Herein, we report a cascade photo\u2010induced radical cyclization (PIRC) strategy for the programmable synthesis of a series of peripheral nitrogen\u2010doped NGs with tunable monolayer and bilayer architectures. Starting from nitrogen\u2010doped nanographene\n                    <jats:bold>1<\/jats:bold>\n                    as a versatile structural platform, \u03c0\u2010extension affords the larger monolayer nanographene\n                    <jats:bold>2<\/jats:bold>\n                    , whereas modulation of the peripheral steric substituents enables the formation of a discrete bilayer assembly, (\n                    <jats:bold>3<\/jats:bold>\n                    )\n                    <jats:sub>2<\/jats:sub>\n                    . Single\u2010crystal x\u2010ray diffraction confirmed the monolayer structures of\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    , while NMR spectroscopy, MALDI\u2010TOF mass spectrometry, and DFT calculations revealed that (\n                    <jats:bold>3<\/jats:bold>\n                    )\n                    <jats:sub>2<\/jats:sub>\n                    adopts a bilayer configuration. Compared with the monolayer analogues, the bilayer assembly shows broadened and blue\u2010shifted absorption features characteristic of H\u2010type coupling. More importantly, peripheral N\u2500H functionalities enable solvent\u2010responsive dissociation of the bilayer through hydrogen bonding with oxygen\u2010containing solvents, leading to a solvent\u2010switchable transformation between bilayer and monolayer states. The aggregation behavior of (\n                    <jats:bold>3<\/jats:bold>\n                    )\n                    <jats:sub>2<\/jats:sub>\n                    is governed by the orthogonality between \u03c0\u2013\u03c0 interactions and hydrogen bonding, giving rise to a unique solvent\u2010dependent yet concentration\u2010independent structural transformation.\n                  <\/jats:p>","DOI":"10.1002\/anie.2743830","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T04:12:53Z","timestamp":1790655173000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Monolayer and Bilayer Nitrogen\u2010Doped Nanographenes Constructed by Cascade Cyclization"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7590-5547","authenticated-orcid":false,"given":"Zhen\u2010Lin","family":"Qiu","sequence":"first","affiliation":[{"name":"State Key Laboratory For Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering Xiamen University  Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-9234-2437","authenticated-orcid":false,"given":"Qing\u2010Song","family":"Deng","sequence":"additional","affiliation":[{"name":"State Key Laboratory For Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering Xiamen University  Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qi","family":"Zeng","sequence":"additional","affiliation":[{"name":"State Key Laboratory For Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering Xiamen University  Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiong","family":"Wu","sequence":"additional","affiliation":[{"name":"State Key Laboratory For Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering Xiamen University  Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xuan\u2010Wen","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory For Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering Xiamen University  Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiang\u2010Feng","family":"Xing","sequence":"additional","affiliation":[{"name":"State Key Laboratory For Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering Xiamen University  Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1268-2761","authenticated-orcid":false,"given":"Yuan\u2010Zhi","family":"Tan","sequence":"additional","affiliation":[{"name":"State Key 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