Počet záznamů: 1
Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts
- 1.
SYSNO ASEP 0571311 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts Tvůrce(i) Ulč, J. (CZ)
Jacko, J. (CZ)
Císařová, I. (CZ)
Pospíšil, Lubomír (UOCHB-X) RID, ORCID
Nečas, D. (CZ)
Kotora, M. (CZ)Číslo článku e202300153 Zdroj.dok. European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 26, č. 18 (2023)Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova catalysis ; C−C activation ; C−H activation ; fluorescence ; heterocycles Obor OECD Organic chemistry Způsob publikování Open access Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000971721200001 EID SCOPUS 85152934036 DOI 10.1002/ejoc.202300153 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2024 Elektronická adresa https://doi.org/10.1002/ejoc.202300153
Počet záznamů: 1