Double [4]Helicene-like Naphthobisbenzothiophene Diimides and Their Thienyl-S,S-dioxidized Derivatives with Attractive Solid-State Fluorescence and High Electron Affinity
A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl5-catalyzed cyclization and m-CPBA-mediated oxidation reactions. The functional five-membered ring diimides show a helicene-like geometry, strong solid-state fl...
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Published in: | Organic letters Vol. 25; no. 6; pp. 972 - 976 |
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Main Authors: | , , , , , |
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American Chemical Society
17-02-2023
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Abstract | A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl5-catalyzed cyclization and m-CPBA-mediated oxidation reactions. The functional five-membered ring diimides show a helicene-like geometry, strong solid-state fluorescence, and deep LUMO of −4.37 eV. |
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AbstractList | A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl
-catalyzed cyclization and
-CPBA-mediated oxidation reactions. The functional five-membered ring diimides show a helicene-like geometry, strong solid-state fluorescence, and deep LUMO of -4.37 eV. A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl5-catalyzed cyclization and m-CPBA-mediated oxidation reactions. The functional five-membered ring diimides show a helicene-like geometry, strong solid-state fluorescence, and deep LUMO of −4.37 eV. |
Author | Yi, Xingyu Gao, Junxiang Chen, Huajie Qin, Hanwen Zeng, Weixuan Zheng, Liping |
AuthorAffiliation | Department of Chemistry Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry |
AuthorAffiliation_xml | – name: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry – name: Department of Chemistry |
Author_xml | – sequence: 1 givenname: Xingyu surname: Yi fullname: Yi, Xingyu organization: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry – sequence: 2 givenname: Junxiang surname: Gao fullname: Gao, Junxiang organization: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry – sequence: 3 givenname: Hanwen surname: Qin fullname: Qin, Hanwen organization: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry – sequence: 4 givenname: Liping surname: Zheng fullname: Zheng, Liping organization: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry – sequence: 5 givenname: Weixuan orcidid: 0000-0003-1577-9021 surname: Zeng fullname: Zeng, Weixuan email: wxz20@cam.ac.uk organization: Department of Chemistry – sequence: 6 givenname: Huajie orcidid: 0000-0003-0366-8826 surname: Chen fullname: Chen, Huajie email: chenhjoe@xtu.edu.cn organization: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36732283$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1021/jacs.8b03535 10.1021/jo801619q 10.1039/D0CC04556J 10.1038/43639 10.1021/acs.orglett.0c01421 10.1002/anie.200501681 10.1021/ma4016592 10.1021/ja503499n 10.1021/jacs.0c11053 10.1002/ejoc.201403341 10.1021/acs.chemrev.0c01017 10.1021/ol071369x 10.1002/chem.201805976 10.1039/D0CC06956F 10.1021/jacs.0c00954 10.1021/acs.orglett.6b01708 10.1021/cm010436t 10.1021/ja061372w 10.1021/acs.chemrev.9b00033 10.1021/ol202662s 10.1039/D1SC00044F 10.1016/0009-2614(75)85698-3 10.1002/adma.201204961 10.1021/jacs.6b08664 10.1021/acs.joc.5b01341 10.1002/anie.201508781 10.1055/a-1616-5643 10.1021/ol4005036 10.1021/cr200087r 10.1021/jacs.2c04012 10.1039/C9CC07040K 10.1021/acs.orglett.9b00152 10.1038/s41467-019-10423-6 10.1021/acs.orglett.1c00678 10.1038/nphoton.2013.176 10.1021/acs.joc.9b01502 10.1039/D1CC02693C 10.1002/anie.202201494 10.1039/D0CC04634E 10.1021/ol062615s 10.1016/0009-2614(68)80041-7 10.1021/ol801136k |
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Snippet | A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl5-catalyzed... A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl -catalyzed... |
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Title | Double [4]Helicene-like Naphthobisbenzothiophene Diimides and Their Thienyl-S,S-dioxidized Derivatives with Attractive Solid-State Fluorescence and High Electron Affinity |
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