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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 &amp; 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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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 &amp; 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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GF21-39639L" target="_blank" >GF21-39639L: Syntéza funkčních materiálů katalytickými cyklotrimerizačními a C-C/C-H funkcionalizačními reakcemi</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Applied Organometallic Chemistry

ISSN

0268-2605

e-ISSN

1099-0739

Svazek periodika

38

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

e7621

Kód UT WoS článku

001265535200001

EID výsledku v databázi Scopus

2-s2.0-85197719093