Pyridyl-benzimidazole derivatives decorated with phenylazo substituents and their low-spin iron(II) complexes: a study of the synthesis, structure and photoisomerization

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F23%3A73621962" target="_blank" >RIV/61989592:15310/23:73621962 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216305:26620/23:PU147890

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2023/nj/d2nj04774h" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2023/nj/d2nj04774h</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d2nj04774h" target="_blank" >10.1039/d2nj04774h</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Pyridyl-benzimidazole derivatives decorated with phenylazo substituents and their low-spin iron(II) complexes: a study of the synthesis, structure and photoisomerization

Popis výsledku v původním jazyce

A series of phenylazo-substituted derivatives of pyridyl-benzimidazoles L1-L5 has been synthesized via a modified Mills reaction and their structural, spectral and photoswitching properties were investigated. NMR spectroscopy and single-crystal X-ray diffraction analysis of the desired compounds confirmed their E conformation. The light-induced E &amp; LRARR; Z (also called trans &amp; LRARR; cis) isomerization was monitored using UV-VIS and H-1 NMR spectroscopy that revealed a reversible photochromic behavior governed by first-order kinetics. State-of-the-art meta-dynamics simulations (iMTD-GC) and ab initio calculations (CASSCF-NEVPT2 and STEOM-DLPNO-CCSD) made the analysis of the electronic structures of ligands possible, which helped to explain the bland E-to-Z conversion of L1 and pronounced switching of L2-L5 ligands. Furthermore, the computational studies identified the active wavelengths of E-to-Z conversion and allowed assessing the mechanisms of photoisomerization. Additionally, ligands L1 and L2 were used for the preparation of four ferrous coordination compounds C1-C4 in which the structural and magnetic investigations confirmed the permanent low-spin state and diamagnetic behavior in the solid state. On the other hand, dissolved compounds C1 and C2 are high-spin at room temperature and their blue light irradiation causes the decomplexation instead of the desired E-to-Z isomerization.

Název v anglickém jazyce

Pyridyl-benzimidazole derivatives decorated with phenylazo substituents and their low-spin iron(II) complexes: a study of the synthesis, structure and photoisomerization

Popis výsledku anglicky

A series of phenylazo-substituted derivatives of pyridyl-benzimidazoles L1-L5 has been synthesized via a modified Mills reaction and their structural, spectral and photoswitching properties were investigated. NMR spectroscopy and single-crystal X-ray diffraction analysis of the desired compounds confirmed their E conformation. The light-induced E &amp; LRARR; Z (also called trans &amp; LRARR; cis) isomerization was monitored using UV-VIS and H-1 NMR spectroscopy that revealed a reversible photochromic behavior governed by first-order kinetics. State-of-the-art meta-dynamics simulations (iMTD-GC) and ab initio calculations (CASSCF-NEVPT2 and STEOM-DLPNO-CCSD) made the analysis of the electronic structures of ligands possible, which helped to explain the bland E-to-Z conversion of L1 and pronounced switching of L2-L5 ligands. Furthermore, the computational studies identified the active wavelengths of E-to-Z conversion and allowed assessing the mechanisms of photoisomerization. Additionally, ligands L1 and L2 were used for the preparation of four ferrous coordination compounds C1-C4 in which the structural and magnetic investigations confirmed the permanent low-spin state and diamagnetic behavior in the solid state. On the other hand, dissolved compounds C1 and C2 are high-spin at room temperature and their blue light irradiation causes the decomplexation instead of the desired E-to-Z isomerization.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

<a href="/cs/project/GA22-23760S" target="_blank" >GA22-23760S: Sublimovatelné jednomolekulárni magnety pro přípravu nanostrukturních tenkých filmů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

NEW JOURNAL OF CHEMISTRY

ISSN

1144-0546

e-ISSN

1369-9261

Svazek periodika

47

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

1488-1497

Kód UT WoS článku

000901500700001

EID výsledku v databázi Scopus

2-s2.0-85144759080