Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks
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| Format: | Artículo Open Access |
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Wiley
2024
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| author | Lucia Feriancová Anita Kiss Timothée Cadart Robert Gyepes Ivana Císařová Martin Kotora |
| author_facet | Lucia Feriancová Anita Kiss Timothée Cadart Robert Gyepes Ivana Císařová Martin Kotora Lucia Feriancová Anita Kiss Timothée Cadart Robert Gyepes Ivana Císařová Martin Kotora |
| collection | Wiley Open Access |
| contents | Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks Lucia Feriancová Anita Kiss Timothée Cadart Robert Gyepes Ivana Císařová Martin Kotora Applied Organometallic Chemistry Synthetic options for conversion of indeno[2,1‐c]fluorene‐5,8‐diones into larger polyaromatic compounds with extended π‐conjugated systems were explored. The crucial two‐fold transformation of the five‐membered ketone moieties of indeno[2,1‐c]fluorene‐5,8‐diones was based either on a one‐carbon homologation or on a ring‐expansion reaction which eventually enabled syntheses of compounds possessing substituted tribenzo[a,e,l]indeno[1,2,3‐hi]acephenanthrylenes and [5]helicenes scaffolds. The former was prepared by using a reaction sequence based on Ramirez olefination, intramolecular Heck reaction, and intermolecular Suzuki‐Miyaura cross‐coupling, whereas the latter utilized a sequence comprising Büchner−Curtius−Schlotterbeck reaction and intermolecular Suzuki‐Miyaura cross‐coupling. Scholl reaction of selected [5]helicenes yielded planarized polyaromatic compounds with the tribenzo[a,e,l]indeno[1,2,3‐hi]acephenanthrylene scaffold. Where possible, structures of products were confirmed by X‐ray diffraction analyses. Photophysical properties were determined as well. 10.1002/aoc.7621 http://creativecommons.org/licenses/by-nc/4.0/ |
| doi_str_mv | 10.1002/aoc.7621 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_aoc_7621 |
| institution | Wiley Open Access |
| license_str_mv | http://creativecommons.org/licenses/by-nc/4.0/ |
| publishDate | 2024 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks Lucia Feriancová Anita Kiss Timothée Cadart Robert Gyepes Ivana Císařová Martin Kotora Applied Organometallic Chemistry Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks Lucia Feriancová Anita Kiss Timothée Cadart Robert Gyepes Ivana Císařová Martin Kotora Applied Organometallic Chemistry Synthetic options for conversion of indeno[2,1‐c]fluorene‐5,8‐diones into larger polyaromatic compounds with extended π‐conjugated systems were explored. The crucial two‐fold transformation of the five‐membered ketone moieties of indeno[2,1‐c]fluorene‐5,8‐diones was based either on a one‐carbon homologation or on a ring‐expansion reaction which eventually enabled syntheses of compounds possessing substituted tribenzo[a,e,l]indeno[1,2,3‐hi]acephenanthrylenes and [5]helicenes scaffolds. The former was prepared by using a reaction sequence based on Ramirez olefination, intramolecular Heck reaction, and intermolecular Suzuki‐Miyaura cross‐coupling, whereas the latter utilized a sequence comprising Büchner−Curtius−Schlotterbeck reaction and intermolecular Suzuki‐Miyaura cross‐coupling. Scholl reaction of selected [5]helicenes yielded planarized polyaromatic compounds with the tribenzo[a,e,l]indeno[1,2,3‐hi]acephenanthrylene scaffold. Where possible, structures of products were confirmed by X‐ray diffraction analyses. Photophysical properties were determined as well. 10.1002/aoc.7621 http://creativecommons.org/licenses/by-nc/4.0/ |
| title | Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks |
| topic | Applied Organometallic Chemistry |
| url | https://onlinelibrary.wiley.com/doi/10.1002/aoc.7621 |