Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F23%3A00571320" target="_blank" >RIV/61388955:_____/23:00571320 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/23:00571311 RIV/00216208:11310/23:10464657
Result on the web
<a href="https://hdl.handle.net/11104/0342574" target="_blank" >https://hdl.handle.net/11104/0342574</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.202300153" target="_blank" >10.1002/ejoc.202300153</a>
Alternative languages
Result language
angličtina
Original language name
Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts
Original language description
Herein, we report the design and synthesis of a series of novel cationic nitrogen-embedded polyaromatic hydrocarbons with a planar geometry. The synthetic pathway is based on catalytic C−C/C−H bond activation relay that enabled preparation of regioselectively 5,6,10,11-tetrasubstituted naphtho[2,1,8-ija]quinolizinium salts bearing various types of substituents. Single-crystal X-ray analyses of selected compounds confirmed planarity of the quinolizinium core. Most of the prepared compounds exhibited strong fluorescence (Φs up to >99 %) ranging from 420–600 nm depending on the substitution pattern. According to DFT calculations LUMO is always distributed over the quinolizinium framework regardless of the attached substituents, whereas delocalization of HOMO is related to the substitution pattern. Electrochemical measurements show irreversible reduction of all compounds, which is supported by the calculated location of LUMO orbitals.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
<a href="/en/project/GA21-29124S" target="_blank" >GA21-29124S: REAP and Other Catalytic Reactions in Synthesis of Nitrogen-Embbeded Polyaromatic Hydrocarbons</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
1099-0690
Volume of the periodical
26
Issue of the periodical within the volume
18
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
e202300153
UT code for WoS article
000971721200001
EID of the result in the Scopus database
2-s2.0-85152934036