Detail publikace

Photoswitchable hydrazones with pyridine-based rotors and halogen substituents

KOTÁSKOVÁ, L. JEWULA, P. HERCHEL, R. NEMEC, I. NEUGEBAUER, P.

Originální název

Photoswitchable hydrazones with pyridine-based rotors and halogen substituents

Typ

článek v časopise ve Web of Science, Jimp

Jazyk

angličtina

Originální abstrakt

The Z,E-photoisomerization of pyridine-based hydrazone switches is typically suppressed due to the presence of pyridine-based rotors. The crystal structures of studied compounds were investigated using theoretical methods combining DFT and QT-AIM calculations to unveil the nature and properties of the intramolecular hydrogen bonding. In this study, we introduced a new series of pyridine-based hydrazones anchored with o-halogen substituents (2-X) and investigated their photoswitching abilities using 1H NMR and UV-Vis spectroscopy. The efficiency of the photoisomerization from initial 2-X-Z to the 2-X-E isomer varied, with the highest yield observed for 2-Cl-E (55%). Our findings, supported by DFT calculations, revealed the formation of a new diastereomer, 2-X-E*, upon back-photoisomerization. We demonstrated that hydrazones from the 2-X series can be reversibly photoswitched using irradiation from the UV-Vis range, and additionally, we explored the effect of the halogen atom on their switching capabilities and also on their thermodynamics and kinetics of photoswitching, determining their molecular solar thermal energy storage potential. We report on the E,Z-photoisomerization of hydrazone switches with pyridine-based rotors and halogen-substituted stators.

Klíčová slova

ISOMERIZATION MECHANISM; BASIS-SETS; CRYSTAL; PH

Autoři

KOTÁSKOVÁ, L.; JEWULA, P.; HERCHEL, R.; NEMEC, I.; NEUGEBAUER, P.

Vydáno

27. 6. 2024

Nakladatel

ROYAL SOC CHEMISTRY

Místo

CAMBRIDGE

ISSN

2046-2069

Periodikum

RSC Advances

Ročník

14

Číslo

29

Stát

Spojené království Velké Británie a Severního Irska

Strany od

20856

Strany do

20866

Strany počet

11

URL

https://pubs.rsc.org/en/content/articlelanding/2024/ra/d4ra02909g

BibTex

@article{BUT190011,
  author="Lucie {Kotásková} and Pawel {Jewula} and Radovan {Herchel} and Ivan {Nemec} and Petr {Neugebauer}",
  title="Photoswitchable hydrazones with pyridine-based rotors and halogen substituents",
  journal="RSC Advances",
  year="2024",
  volume="14",
  number="29",
  pages="20856--20866",
  doi="10.1039/d4ra02909g",
  issn="2046-2069",
  url="https://pubs.rsc.org/en/content/articlelanding/2024/ra/d4ra02909g"
}