Issue 28, 2023

A feasible strategy to obtain air-stable triphenylamine radicals in the solid state by introducing conjugated donor–acceptor modules

Abstract

In recent years, organic radicals have gained considerable attention because they open opportunities for new-generation electronics which may integrate spin, magnetic and quantum mechanical effects. However, air stable organic radicals in the solid state, which can be practically applied, remain a great challenge in chemistry. Herein, we choose N-heptanamido triarylamine as a fragment which can produce radicals upon light irradiation, phenothiazine as a donor (D) unit, and 3-ethylrhodanine or 1,3-indanedione as an acceptor (A) unit, and then connect them in a conjugated manner. The results of 1H-NMR spectroscopy, DFT calculations, EPR measurements, AFM and photophysical characterization revealed that the introduction of the D unit could significantly increase spin delocalization and then the stability of the light-triggered TPA radicals in chloroform solution. These radicals can be maintained in the solid state. More importantly, these become stable radicals with a half-life of approximately one month under ambient conditions due to the stronger intermolecular aggregation resulting from the introduction of the A unit. This work provides a new approach for obtaining air-stable radicals in the solid-state from organic radicals in solution.

Graphical abstract: A feasible strategy to obtain air-stable triphenylamine radicals in the solid state by introducing conjugated donor–acceptor modules

Supplementary files

Article information

Article type
Paper
Submitted
04 Apr 2023
Accepted
26 May 2023
First published
30 May 2023

J. Mater. Chem. C, 2023,11, 9640-9648

A feasible strategy to obtain air-stable triphenylamine radicals in the solid state by introducing conjugated donor–acceptor modules

X. Rong, J. Liu, J. Wu, C. Li, K. Wang, Z. Lu, Y. Liu, M. Gu and Y. Huang, J. Mater. Chem. C, 2023, 11, 9640 DOI: 10.1039/D3TC01187A

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