Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems
The scope of Rh-catalyzed C–C bond cleavage/annulation of biphenylene with various aromatic nitriles was studied. The subsequent Rh- and Ir-catalyzed C–H bond activation/annulation sequence of the formed 9-arylphenanthridines with alkynes gave rise to cationic [4], [5], [6] helical quinolizinium sal...
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MDPI AG
2023-05-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/13/5/912 |
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| author | Samuel Hrubý Jan Ulč Ivana Císařová Martin Kotora |
| author_facet | Samuel Hrubý Jan Ulč Ivana Císařová Martin Kotora |
| author_sort | Samuel Hrubý |
| collection | DOAJ |
| description | The scope of Rh-catalyzed C–C bond cleavage/annulation of biphenylene with various aromatic nitriles was studied. The subsequent Rh- and Ir-catalyzed C–H bond activation/annulation sequence of the formed 9-arylphenanthridines with alkynes gave rise to cationic [4], [5], [6] helical quinolizinium salts. The scope of the reaction with respect to the structural features of the starting 9-arylphenanthridines and alkynes was studied. Their helical arrangement was confirmed through single-crystal X-ray analyses of selected compounds. Most of the prepared quinolizinium salts exhibited fluorescence emission maxima in the region of 525–623 nm with absolute quantum yields up to 25%. |
| first_indexed | 2024-03-11T03:52:18Z |
| format | Article |
| id | doaj.art-fc4f8aa039f64bb48c470441c39489b6 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T03:52:18Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-fc4f8aa039f64bb48c470441c39489b62023-11-18T00:52:08ZengMDPI AGCatalysts2073-43442023-05-0113591210.3390/catal13050912Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated SystemsSamuel Hrubý0Jan Ulč1Ivana Císařová2Martin Kotora3Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague, Czech RepublicDepartment of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague, Czech RepublicDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague, Czech RepublicDepartment of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague, Czech RepublicThe scope of Rh-catalyzed C–C bond cleavage/annulation of biphenylene with various aromatic nitriles was studied. The subsequent Rh- and Ir-catalyzed C–H bond activation/annulation sequence of the formed 9-arylphenanthridines with alkynes gave rise to cationic [4], [5], [6] helical quinolizinium salts. The scope of the reaction with respect to the structural features of the starting 9-arylphenanthridines and alkynes was studied. Their helical arrangement was confirmed through single-crystal X-ray analyses of selected compounds. Most of the prepared quinolizinium salts exhibited fluorescence emission maxima in the region of 525–623 nm with absolute quantum yields up to 25%.https://www.mdpi.com/2073-4344/13/5/912C–C bond activationC–H bond activationhelicenescatalysisrhodiumfluorescence |
| spellingShingle | Samuel Hrubý Jan Ulč Ivana Císařová Martin Kotora Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems Catalysts C–C bond activation C–H bond activation helicenes catalysis rhodium fluorescence |
| title | Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems |
| title_full | Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems |
| title_fullStr | Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems |
| title_full_unstemmed | Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems |
| title_short | Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems |
| title_sort | synthesis of cationic 4 5 and 6 azahelicenes with extended π conjugated systems |
| topic | C–C bond activation C–H bond activation helicenes catalysis rhodium fluorescence |
| url | https://www.mdpi.com/2073-4344/13/5/912 |
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