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Recently, thiophene\u2010containing multiple helicenes have garnered enormous attention due to their intriguing electronic and (chir)optical properties compared with carbohelicenes. However, the efficient synthesis of thiopyran\u2010containing multiple helicenes and the underlying sulfur doping mechanisms are rather unexplored. Herein, the synthesis and structural analysis of a thiopyran\u2010containing double [7]helicene\n                    <jats:bold>3<\/jats:bold>\n                    are reported. X\u2010ray crystallographic analysis reveals\n                    <jats:bold>3<\/jats:bold>\n                    and its dication with\n                    <jats:italic>C<\/jats:italic>\n                    <jats:sub>2<\/jats:sub>\n                    \u2010symmetric propeller\u2010shape structures and compact interactions in the solid state.\n                    <jats:bold>3<\/jats:bold>\n                    exhibits deep\u2010red to near\u2010infrared (NIR) fluorescence emission. Tunable aromaticity of the central benzene ring and thiopyran rings is found by chemical oxidation, which is further confirmed by nucleus\u2010independent chemical shift (NICS), anisotropy of the induced current density (ACID) and harmonic oscillator model of aromaticity (HOMA) analysis. Furthermore, the chiral and photosensitizing characters of\n                    <jats:bold>3<\/jats:bold>\n                    are investigated. The excellent deep\u2010red to NIR fluorescence, circularly polarized luminescence (CPL) and photosensitizing activities suggest that\n                    <jats:bold>3<\/jats:bold>\n                    can be used as an outstanding photosensitizer in photodynamic therapy (PDT) and bioimaging, especially paving the way for future CPL\u2010PDT and CPL\u2010bio\u2010probe applications.\n                  <\/jats:p>","DOI":"10.1002\/anie.202412681","type":"journal-article","created":{"date-parts":[[2024,8,8]],"date-time":"2024-08-08T09:45:22Z","timestamp":1723110322000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["A Deep\u2010Red Emissive Sulfur\u2010Doped Double [7]Helicene Photosensitizer: Synthesis, Structure and Chiral Optical Properties"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-0363-9107","authenticated-orcid":false,"given":"Wen\u2010Wen","family":"Yang","sequence":"first","affiliation":[{"name":"School of the Environment and Safety Engineering Jiangsu University  Zhenjiang 212013 Jiangsu P. 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