Diporphyrin tweezer for multichannel spectroscopic analysis of enantiomeric excess

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F20%3A10420630" target="_blank" >RIV/00216208:11320/20:10420630 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=~oJYc9pbwk" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=~oJYc9pbwk</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11705-019-1869-1" target="_blank" >10.1007/s11705-019-1869-1</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Diporphyrin tweezer for multichannel spectroscopic analysis of enantiomeric excess

Popis výsledku v původním jazyce

Chiral 1,1&apos;-binaphthyl-linked diporphyrin &apos;tweezers&apos; (R)-1/(S)-1 and the corresponding zinc(II) complexes (R)-2/(S)-2 were prepared as chiral host molecules, and their utility for chiral analyses (especially enantiomeric excess (ee) determinations) were evaluated. Tris(1-n-dodecyl)porphyrins were used for the first time as the interacting units. Host capabilities of the diporphyrin tweezers were investigated by titrations with (R,R)- and (S,S)-cyclohexane-1,2-diamine (CHDA). The host molecules could be used as multichannel probes of ee by using UV-vis, circular dichroism (CD), fluorescence emission and H-1 nuclear magnetic resonance (H-1-NMR) methods. Chiral configurations could also be differentiated using CD or H-1-NMR spectroscopy. All three optical techniques give good resolution of ee with reasonable sensitivity considering the low concentrations used (ca. 10(-6) mol center dot L-1). The ee determination of CHDA enantiomers using NMR spectroscopy is also possible because of the reasonably well separated resonances in the case of (R,R)- and (S,S)-CHDA. Non-metallated (R)-1/(S)-1 hosts could not be used to detect chiral information in a strongly acidic chiral guest. This work demonstrates the utility of 1,1&apos;-binapthyl-linked chiral hosts for chiral analysis of ditopically interacting enantiomers.

Název v anglickém jazyce

Diporphyrin tweezer for multichannel spectroscopic analysis of enantiomeric excess

Popis výsledku anglicky

Chiral 1,1&apos;-binaphthyl-linked diporphyrin &apos;tweezers&apos; (R)-1/(S)-1 and the corresponding zinc(II) complexes (R)-2/(S)-2 were prepared as chiral host molecules, and their utility for chiral analyses (especially enantiomeric excess (ee) determinations) were evaluated. Tris(1-n-dodecyl)porphyrins were used for the first time as the interacting units. Host capabilities of the diporphyrin tweezers were investigated by titrations with (R,R)- and (S,S)-cyclohexane-1,2-diamine (CHDA). The host molecules could be used as multichannel probes of ee by using UV-vis, circular dichroism (CD), fluorescence emission and H-1 nuclear magnetic resonance (H-1-NMR) methods. Chiral configurations could also be differentiated using CD or H-1-NMR spectroscopy. All three optical techniques give good resolution of ee with reasonable sensitivity considering the low concentrations used (ca. 10(-6) mol center dot L-1). The ee determination of CHDA enantiomers using NMR spectroscopy is also possible because of the reasonably well separated resonances in the case of (R,R)- and (S,S)-CHDA. Non-metallated (R)-1/(S)-1 hosts could not be used to detect chiral information in a strongly acidic chiral guest. This work demonstrates the utility of 1,1&apos;-binapthyl-linked chiral hosts for chiral analysis of ditopically interacting enantiomers.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Frontiers of Chemical Science and Engineering

ISSN

2095-0179

e-ISSN

—

Svazek periodika

14

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

CN - Čínská lidová republika

Počet stran výsledku

13

Strana od-do

28-40

Kód UT WoS článku

000519253800004

EID výsledku v databázi Scopus

2-s2.0-85077579352