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

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F24%3A10490483" target="_blank" >RIV/00216208:11310/24:10490483 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=ESKhEzuFK_" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=ESKhEzuFK_</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/aoc.7621" target="_blank" >10.1002/aoc.7621</a>

Result language
angličtina
Original language name
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
Original language description
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 B & uuml;chner-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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GF21-39639L" target="_blank" >GF21-39639L: Catalytic Cyclotrimerization and C-C/C-H Functionalization Reactions in the Synthesis of Functional Molecules</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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