Issue 16, 2023

Thermal-responsive ground-state spin switching in novel butterfly-shaped overcrowded ethylene featuring a benzodithiophene core

Abstract

A novel class of butterfly-shaped overcrowded ethylenes (OCEs), featuring a heterocyclic benzodithiophene (BDT) core, has been synthesized and investigated. X-ray crystallography analysis revealed that the BDT core exhibits an almost planar geometry, distinct from the well-studied AQD-based OCEs with a polycyclic aromatic hydrocarbon core. Under thermal stimuli, open-shell species of the BDT-based overcrowded ethylene (BD) were accessible in solution, as confirmed by variable-temperature 1H NMR and ESR spectroscopy. Theoretical studies propose that the ground-state spin switching behavior of BD is primarily attributed to the rotation of the terminal trifluoromethylbenzene (TFB) groups. Open-shell species could be generated when the dihedral angles between the benzodithiophene core and terminal TFB groups twisted to approximately 40°, without requiring an orthogonal conformation through rotation.

Graphical abstract: Thermal-responsive ground-state spin switching in novel butterfly-shaped overcrowded ethylene featuring a benzodithiophene core

Supplementary files

Article information

Article type
Research Article
Submitted
09 Jun 2023
Accepted
26 Jun 2023
First published
29 Jun 2023

Org. Chem. Front., 2023,10, 3989-3994

Thermal-responsive ground-state spin switching in novel butterfly-shaped overcrowded ethylene featuring a benzodithiophene core

Y. Han, F. Ying, E. Wu, X. Yu, G. Gao, J. Xie and X. Jin, Org. Chem. Front., 2023, 10, 3989 DOI: 10.1039/D3QO00866E

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