Publication detail

Fast E/Z UV-light response T-type photoswitching of phenylene-thienyl imines

VESELÝ, D. JANČÍK, J. WEITER, M. BLASI, D. IVANOVA, N. KRAJČOVIČ, J. GEORGIEV, A.

Original Title

Fast E/Z UV-light response T-type photoswitching of phenylene-thienyl imines

Type

journal article in Web of Science

Language

English

Original Abstract

New types of imine switches containing an alkylated para-bis(2-thienyl)phenylene moiety have been synthesized and studied. A bis substituted 2,4-diiminotoluene with phenylene-thienyl unit has also been synthesized and studied to evaluate the bifunctional switching of the imine bonds. Fast E/Z response in toluene and acetonitrile under 365 nm UV-light illumination was observed. It was found that the thermally unstable Z isomers are recovered to E ones in the dark by different rate constants depending on the solvent polarity, which refers to the T-type photochromic switches. The DFT calculations have shown that the switched Z forms are characterized by near perpendicular (T-shaped) orientation of the aromatic amine rings with respect to the thiophene one. The emission exhibited a significant bathochromism varying the solvent polarity, with Stokes shifts reaching values in the order 10 000 cm-1, while the absorption remained almost unaffected. Therefore, the relationship between E/Z switching response and solvent sensitivity of the emissions was estimated. The behaviour of the compounds suggests a rapid T-type E/Z/E isomerization cycle and dynamic control over the light-driven geometrical changes of the imine bond.

Keywords

Imines; Photoswitches; E; Z isomerization; T-type photochromism; DFT calculations

Authors

VESELÝ, D.; JANČÍK, J.; WEITER, M.; BLASI, D.; IVANOVA, N.; KRAJČOVIČ, J.; GEORGIEV, A.

Released

1. 9. 2022

Publisher

ELSEVIER SCIENCE SA

Location

LAUSANNE

ISBN

1010-6030

Periodical

Journal of Photochemistry and Photobiology A:Chemistry

Year of study

430

Number

9

State

Swiss Confederation

Pages from

1

Pages to

8

Pages count

8

URL

https://doi.org/10.1016/j.jphotochem.2022.113994

BibTex

@article{BUT178203,
  author="VESELÝ, D. and JANČÍK, J. and WEITER, M. and BLASI, D. and IVANOVA, N. and KRAJČOVIČ, J. and GEORGIEV, A.",
  title="Fast E/Z UV-light response T-type photoswitching of phenylene-thienyl imines",
  journal="Journal of Photochemistry and Photobiology A:Chemistry",
  year="2022",
  volume="430",
  number="9",
  pages="1--8",
  doi="10.1016/j.jphotochem.2022.113994",
  issn="1010-6030",
  url="https://doi.org/10.1016/j.jphotochem.2022.113994"
}

Responsibility: Ing. Marek Strakoš