Aethrene: A Stable Polycyclic Aromatic Hydrocarbon With a Triplet Ground State
Abstract
ABSTRACT Owing to their unique electronic structures and magnetic properties, high‐spin radicals have garnered significant interest in the fields of organic electronics and spintronics. Nevertheless, the high reactivity of high‐spin radicals renders efficient synthesis and selective isolation of the species a formidable challenge. An aethrene derivative 2 with an A‐shaped geometric skeleton was designed with a Clar structure of allylic radicals embedded with aromatic benzenoid rings, and two bulky steric substituents were introduced at the zigzag edges to endow the compound with excellent stability. 2 exhibits a 15.5‐day half‐life under ambient and light conditions. The structure of 2 was unequivocally confirmed through x‐ray crystallographic analysis. Aethrene 2 was demonstrated to possess a triplet ground state through DFT calculations and experimental methods, including continuous wave and pulsed electron paramagnetic resonance and superconducting quantum interference device measurements. Notably, its dication was successfully obtained by in‐situ oxidation with NO·SbF 6 and exhibited a closed‐shell ground state. This work shed new light on the design and synthesis of novel stable PAHs with high‐spin multiplicity.
Article Details
Authors (9)
Junqin Xie
Centre for Statistics in Medicine and National Institute for Health and Care Research Biomedical Research Centre Oxford, Nuffield Department of Orthopaedics, Rheumatology and Musculoskeletal Sciences, University of Oxford
Ya Zou
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Wen Ji
Lei Wang
Weiwei Niu
Center of Single-Molecule Sciences, Institute of Modern Optics, Tianjin Key Laboratory of Micro-Scale Optical Information Science and Technology, College of Electronic Information and Optical Engineering, Nankai University, 38 Tongyan Road, Jinnan District, Tianjin 300350, China
Yin Yang
State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry
Xiongwei Qu
Hebei Key Laboratory of Functional Polymers, School of Chemical Engineering and Technology
Jishan Wu
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Guangwu Li
Center of Single-Molecule Sciences, Institute of Modern Optics, Tianjin Key Laboratory of Micro-Scale Optical Information Science and Technology, College of Electronic Information and Optical Engineering