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Herein, a series of carbon\u2010bridged spiro\u2010type heterosumanenes (spiro\u2010HSEs) were synthesized by combining 9,9\u2032\u2010spirobifluorene and dichalcogenasumanenes (DCSs). It is found that spiro\u2010conjugation plays an important role in the geometric and electronic structures of spiro\u2010HSEs. The bowl depth of DCSs moiety becomes larger in the spiro\u2010HSEs. Owing to the Jahn\u2010Teller (<jats:italic>J\u2010T<\/jats:italic>) effect, two DCSs segments of spiro\u2010HSEs have different bowl depths accompanied with the unequal distribution of charge in radical cation state. Taking advantage of the typical reactions of DCSs, selective transformations of spiro\u2010HSEs have been adopted in accordance to the nature of chalcogen atoms (S, Se, Te) to bestow the value\u2010added functionalities. The emissive property is enhanced by converting the thiophene rings of S\u2010doped spiro\u2010HSE into thiophene <jats:italic>S,S<\/jats:italic>\u2010dioxides. A chiroptical polycycle could be produced by ring\u2010opening of the edge benzene of Se\u2010doped spiro\u2010HSE. The covalent adduct of Te\u2010doped spiro\u2010HSE with Br<jats:sub>2<\/jats:sub> forms non\u2010centrosymmetric halogen\u2010bonded networks, resulting in the high performance second\u2010order nonlinear optics (NLO).<\/jats:p>","DOI":"10.1002\/anie.202414231","type":"journal-article","created":{"date-parts":[[2024,8,13]],"date-time":"2024-08-13T11:30:54Z","timestamp":1723548654000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Spiro\u2010Buckybowls: Synthesis and Selective Transformations Toward Chiral and Nonlinear Optical Polycycles"],"prefix":"10.1002","volume":"63","author":[{"given":"Jihai","family":"Shang","sequence":"first","affiliation":[{"name":"Research Center for Free Radical Chemistry State Key Laboratory of Applied Organic Chemistry Lanzhou University  Tianshui Southern Road 222 Lanzhou Gansu Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhihua","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Materials Science and Engineering Smart Sensing Interdisciplinary Science Center Frontiers Science Center for New Organic Matter Nankai University  Tongyan Road 38 Tianjin 300350 P. 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