Počet záznamů: 1
Designing Powerful Biindole-Based Inherently Chiral Selectors: Enhancing Enantiodiscrimination by Core Functionalization with Additional Coordination Elements
- 1.
SYSNO ASEP 0584857 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Designing Powerful Biindole-Based Inherently Chiral Selectors: Enhancing Enantiodiscrimination by Core Functionalization with Additional Coordination Elements Tvůrce(i) Grecchi, S. (IT)
Bonetti, G. (IT)
Emanuele, E. (IT)
Ludvík, Jiří (UFCH-W) RID, ORCID
Koláčná, Lucie (UFCH-W) ORCID, RID, SAI
Liška, Alan (UFCH-W) RID, ORCID
Hromadová, Magdaléna (UFCH-W) RID, ORCID, SAI
Arnaboldi, S. (IT)
Cirilli, R. (IT)
Mussini, P. R. (IT)
Benincori, T. (IT)Číslo článku e202303530 Zdroj.dok. Chemistry - A European Journal. - : Wiley - ISSN 0947-6539
Roč. 30, č. 23 (2024)Poč.str. 16 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova electrochemistry ; potentials ; electrode ; naproxen ; pharmaceuticals ; sensor ; Biindole-based inherently chiral selectors ; Additional coordination elements enhancing enantiodiscrimination ; Chiral electrode surfaces by electrooligomerization ; Chiral voltammetry ; Enantiodiscrimination in voltammetric analysis of naproxen and ketoprofen NSAIDs Vědní obor RIV CG - Elektrochemie Obor OECD Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis) CEP GA21-23261S GA ČR - Grantová agentura ČR GA21-13458S GA ČR - Grantová agentura ČR Výzkumná infrastruktura e-INFRA CZ II - 90254 - CESNET, zájmové sdružení právnických osob Způsob publikování Omezený přístup Institucionální podpora UFCH-W - RVO:61388955 UT WOS 001189109600001 EID SCOPUS 85188321036 DOI 10.1002/chem.202303530 Anotace Among inherently chiral selectors of axial stereogenicity, usually resulting in very good enantiodiscrimination performances, the biindole-based family has the additional advantage of very easy functionalization of the two nitrogen atoms with a variety of substituents with desirable properties. Aiming to evaluate the possibility of exploiting such feature to enhance the enantiodiscrimination ability of the archetype structure, a series of three inherently chiral monomers were designed and synthesized, characterised by a 2,2´-biindole atropisomeric core conjugated to bithiophene wings enabling fast and regular electrooligomerization, and functionalised at the nitrogen atoms with an ethyl, a methoxyethyl, or a hydroxyethyl substituent. Nitrogen alkylation was also exploited to obtain for the first time the chemical resolution of the biindole selectors without employing chiral HPLC. The enantiodiscrimination ability of the selector series was comparatively evaluated in proof-of-concept chiral voltammetry experiments with a ´´benchmark´´ chiral ferrocenyl probe as well as with chiral non-steroidal anti-inflammatory drugs naproxen and ketoprofen. The large enantiomer potential differences for all probes increased in the ethyl < methoxyethyl MUCH LESS-THAN hydroxyethyl sequence of selector substituents, supporting our assumption on the beneficial role of an additional coordination element. The powerful hydroxyethyl selector was also applied to ketoprofen in a commercial drug matrix. Pracoviště Ústav fyzikální chemie J.Heyrovského Kontakt Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Rok sběru 2025 Elektronická adresa https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202303530
Počet záznamů: 1