Spectroscopic study on enantiomeric Ni(II) complexes of porphyrin-porphyrin Tröger's base and porphyrin-chlorin spiro-Tröger's base derivatives supported by DFT calculations

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F24%3A43928853" target="_blank" >RIV/60461373:22340/24:43928853 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1016/j.saa.2024.124308" target="_blank" >https://doi.org/10.1016/j.saa.2024.124308</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.saa.2024.124308" target="_blank" >10.1016/j.saa.2024.124308</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Spectroscopic study on enantiomeric Ni(II) complexes of porphyrin-porphyrin Tröger's base and porphyrin-chlorin spiro-Tröger's base derivatives supported by DFT calculations

Popis výsledku v původním jazyce

The chiral properties of nickel(II) complexes of porphyrin-porphyrin Tröger&apos;s base and porphyrin-chlorin spiro-Tröger&apos;s base with phenyl or 3-methoxyphenyl substitutions in their meso-positions were studied. Enantioseparation of racemic mixtures was investigated via high-performance liquid chromatography (HPLC) on an analytical ReproSil Chiral-NR column. The optimal conditions were utilized for a multimilligram scale isolation with a semipreparative column. The purity of the isolated enantiomers was determined by HPLC and UV–Vis spectroscopy. The absolute configurations of the isolated enantiomers were determined by evaluating the Cotton effect in electronic circular dichroism spectra. The determination was supported by TDDFT calculations, in which good agreement was achieved between the experimental and simulated spectra. The maximum molar ellipticity values, [θ]λmax given in deg ∙ cm2 ∙ dmol−1, were [θ]435 = 1.73 ∙ 107 for phenyl spiroTB and [θ]436 = 1.24 ∙ 107 and [θ]436 = 2.15 ∙ 107 for 3-methoxyphenyl TB and spiroTB, respectively.

Název v anglickém jazyce

Spectroscopic study on enantiomeric Ni(II) complexes of porphyrin-porphyrin Tröger's base and porphyrin-chlorin spiro-Tröger's base derivatives supported by DFT calculations

Popis výsledku anglicky

The chiral properties of nickel(II) complexes of porphyrin-porphyrin Tröger&apos;s base and porphyrin-chlorin spiro-Tröger&apos;s base with phenyl or 3-methoxyphenyl substitutions in their meso-positions were studied. Enantioseparation of racemic mixtures was investigated via high-performance liquid chromatography (HPLC) on an analytical ReproSil Chiral-NR column. The optimal conditions were utilized for a multimilligram scale isolation with a semipreparative column. The purity of the isolated enantiomers was determined by HPLC and UV–Vis spectroscopy. The absolute configurations of the isolated enantiomers were determined by evaluating the Cotton effect in electronic circular dichroism spectra. The determination was supported by TDDFT calculations, in which good agreement was achieved between the experimental and simulated spectra. The maximum molar ellipticity values, [θ]λmax given in deg ∙ cm2 ∙ dmol−1, were [θ]435 = 1.73 ∙ 107 for phenyl spiroTB and [θ]436 = 1.24 ∙ 107 and [θ]436 = 2.15 ∙ 107 for 3-methoxyphenyl TB and spiroTB, respectively.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LTAUSA19065" target="_blank" >LTAUSA19065: Příprava a studium vlastností metaloporfyrinových derivátů Trögerových, spiro-Trögerových a oligo-Trögerových bází</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY

ISSN

1386-1425

e-ISSN

1873-3557

Svazek periodika

316

Číslo periodika v rámci svazku

5 August 2024

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

7

Strana od-do

—

Kód UT WoS článku

001217017600001

EID výsledku v databázi Scopus

2-s2.0-85190942811