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Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts
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SYSNO ASEP 0571311 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts Author(s) Ulč, J. (CZ)
Jacko, J. (CZ)
Císařová, I. (CZ)
Pospíšil, Lubomír (UOCHB-X) RID, ORCID
Nečas, D. (CZ)
Kotora, M. (CZ)Article number e202300153 Source Title European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 26, č. 18 (2023)Number of pages 10 s. Language eng - English Country DE - Germany Keywords catalysis ; C−C activation ; C−H activation ; fluorescence ; heterocycles OECD category Organic chemistry Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 000971721200001 EID SCOPUS 85152934036 DOI 10.1002/ejoc.202300153 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2024 Electronic address https://doi.org/10.1002/ejoc.202300153
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