Synthesis and structure elucidation of triarylmethyl radicals with anthryl substitution

Wang, Peng; Hu, Jinlian; Xu, Zhuofan; Pu, Zhaofangzhou; Sato, Sota; Zhang, Xiaotao; Hu, Wenping; Sun, Zhe

doi:10.1039/d2cc06083c

Chem. Commun.

2023

DOI: 10.1039/d2cc06083c

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Synthesis and structure elucidation of triarylmethyl radicals with anthryl substitution

Peng Wang

Jinlian Hu

Zhuofan Xu

et al.

Abstract: Two stable triarylmethyl radicals with one or two anthryl substitutions are synthesized in gram scale, and are isolated in the crystalline state. Detailed structural elucidation with X-ray crystallographic analysis and...

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Cited by 4 publications

References 40 publications

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Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

Tang,

Zhu,

Jin

et al. 2024

Angewandte Chemie

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The development of novel luminescent radicals, characterized by their unique doublet emission, endows a significant challenge. In this study, we reported the synthesis of a luminescent neutral radical, BCzAnM‐R, tailored by two carbazolyl groups and an anthryl group to achieve a nonalternant structure. It exhibited near‐infrared emission with a peak at 1020 nm in toluene. Interestingly, its corresponding cation, BCzAnM‐C, was synthesized through an unconventional SnCl2‐mediated reduction‐aromatization‐oxidation reaction in one‐pot and gram‐scale. The cation demonstrated remarkable stability for up to weeks in ambient conditions and facilitated the silica‐gel chromatography isolation as an organic salt with SnCl3‐ as the counter ion. The carbazolyl groups effectively modulate molecular structures, photophysical properties, and stabilities. Notably, BCzAnM‐R represents the first luminescent triarylmethyl radical with two carbazolyl groups directly attached to the central carbon.

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Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

Tang,

Zhu,

Jin

et al. 2024

Angewandte Chemie

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Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

Tang,

Zhu,

Jin

et al. 2024

Angew Chem Int Ed

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Generation and Characterization of a Tetraradical Embedded in a Curved Cyclic Paraphenylene Unit

Miyazawa

Wang

Hatano

et al. 2023

Chemistry A European J

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Unique spin-spin (magnetic) interactions, ring-size effects on ground-state spin multiplicity, and in-plane aromaticity has been found in localized 1,3-diradicals embedded in curved benzene structures such as cycloparaphenylene (CPP). In this study, we characterized the magnetic interactions in a tetraradical consisting of two localized 1,3diradical units connected by p-quaterphenyl within a curved CPP skeleton by electron paramagnetic resonance (EPR) spectroscopy and quantum chemical calculations. Persistent triplet species with zero-field splitting parameters similar to those of a triplet 1,3-diphenylcyclopentane-1,3-diyl diradical were observed by continuous wave (CW) or pulsed X-band EPR measurements. The quintet state derived from the ferromagnetic interaction between the two triplet diradical moieties was not detected at 20 K under glassy matrix conditions. At the B3LYP/6-31G(d) level of theory, the singlet state was lower in energy than the triplet and quintet states. These findings will aid in the development of open-shell species for material science application.

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Synthesis and structure elucidation of triarylmethyl radicals with anthryl substitution

Abstract: Two stable triarylmethyl radicals with one or two anthryl substitutions are synthesized in gram scale, and are isolated in the crystalline state. Detailed structural elucidation with X-ray crystallographic analysis and...

Cited by 4 publications

References 40 publications

Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

Generation and Characterization of a Tetraradical Embedded in a Curved Cyclic Paraphenylene Unit

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