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In this study, we report an unexpected azulene\u2010to\u2010phenanthrene rearrangement during the Scholl reaction of tetraarylated biazulene precursors. Combined experimental and computational studies suggest that this transformation proceeds through a proton\u2010promoted, arenium\u2010ion\u2010mediated rearrangement pathway. A key intermediate product\n                    <jats:bold>1a\u2013i<\/jats:bold>\n                    was isolated and fully characterized, providing direct insight into the rearrangement process. This transformation enables efficient access to a series of substituted nanographenes. Comprehensive photophysical and electrochemical characterization, together with density functional theory calculations, demonstrate that the resulting nanographenes\n                    <jats:bold>1a<\/jats:bold>\n                    \u2013\n                    <jats:bold>1d<\/jats:bold>\n                    possess tunable optical and electrochemical properties that can be modulated by peripheral substituents. Moreover, single\u2010crystal x\u2010ray diffraction confirmed the structures of nanographenes\n                    <jats:bold>1a<\/jats:bold>\n                    ,\n                    <jats:bold>1c<\/jats:bold>\n                    ,\n                    <jats:bold>1d<\/jats:bold>\n                    , and\n                    <jats:bold>1a\u2013i<\/jats:bold>\n                    . Their flapping\u2010wing conformation and globally aromatic \u03c0\u2010conjugated framework contribute to the pronounced two\u2010photon absorption (TPA) responses of these nanographenes. Their TPA cross sections are tunable and reach up to 1239 GM, representing remarkable TPA performance among molecular nanographenes. This work reveals an unusual rearrangement pathway of azulene motifs under a mild condition and provides a useful strategy for accessing nanographenes with tunable electronic structures and nonlinear optical properties.\n                  <\/jats:p>","DOI":"10.1002\/anie.8651160","type":"journal-article","created":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T06:21:11Z","timestamp":1789626071000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Unexpected Azulene\u2010to\u2010Naphthalene Rearrangement Enables the Synthesis of Nanographenes with Tunable Two\u2010Photon Absorption"],"prefix":"10.1002","author":[{"given":"Yang","family":"Chao","sequence":"first","affiliation":[{"name":"MOE Key Laboratory of Bioorganic Phosphorous and Chemical Biology Department of Chemistry Tsinghua University  Beijing P. R. 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