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Herein, we introduce a paradigm\u2010shifting strategy\u2014stereoelectronic planarity disruption of molecular planarity\u2014to transform this detrimental trade\u2010off into a synergistic, aggregation\u2010enhanced process. By integrating sterically demanding and electronically communicative peripheries into an acceptor\u2013donor\u2013acceptor\u2013donor\u2013acceptor (A\u2013DA'D\u2013A) scaffold, we designed small molecules (AS4T and AS4Se) that exhibit concurrent aggregation\u2010enhanced ROS and fluorescence efficiencies. This unique design, verified by theoretical and structural analyses, alleviates detrimental \u03c0\u2013\u03c0 interactions to simultaneously promote intersystem crossing and radiative decay in the aggregate state. The derived nanoparticles (NPs), particularly AS4T NPs, achieve a record\u2010high\n                    <jats:sup>1<\/jats:sup>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    quantum yield (24.7%), robust O\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2022\u2212<\/jats:sup>\n                    production, and 6.3\u2010fold higher NIR\u2010II brightness than ICG\/FBS. Under low\u2010power 808\u00a0nm laser irradiation, AS4T NPs enable high\u2010contrast tumor imaging and complete tumor elimination through photodynamic therapy alone, even for deep\u2010seated tumors. This work establishes a new design paradigm that unifies aggregation\u2010enhanced ROS and fluorescence efficiency in NIR\u2010II fluorescent photosensitizers, offering a transformative approach to highly efficient tumor phototheranostics.\n                  <\/jats:p>","DOI":"10.1002\/smll.202514912","type":"journal-article","created":{"date-parts":[[2026,3,12]],"date-time":"2026-03-12T09:53:35Z","timestamp":1773309215000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Tuning Photophysical Conflict Into Synergy: Stereoelectronic Planarity Disruption Unlocks Concurrent Aggregation\u2010Enhanced ROS and NIR\u2010II Fluorescence"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6420-7930","authenticated-orcid":false,"given":"Jie","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; Institute of Advanced Materials (IAM) School of Flexible Electronics (Future Technologies) Nanjing Tech University (NanjingTech)  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dalong","family":"Ma","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; Institute of Advanced Materials (IAM) School of Flexible Electronics (Future Technologies) Nanjing Tech University (NanjingTech)  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wen","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; Institute of Advanced Materials (IAM) School of Flexible Electronics (Future Technologies) Nanjing Tech University (NanjingTech)  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xunwen","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; Institute of Advanced Materials (IAM) School of Flexible Electronics (Future Technologies) Nanjing Tech University (NanjingTech)  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiangwei","family":"Cui","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; Institute of Advanced Materials (IAM) School of Flexible Electronics (Future Technologies) Nanjing Tech University (NanjingTech)  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mengjie","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; Institute of Advanced Materials (IAM) School of Flexible Electronics (Future Technologies) Nanjing Tech University (NanjingTech)  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Longling","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Flexible Electronics (LoFE) &amp; 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