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

Rong, Xugang; Liu, Jueshan; Wu, Jianglin; Li, Chuan; Wang, Kexin; Lu, Zhiyun; Liu, Yingzhe; Gu, Mingjie; Huang, Yan

doi:10.1039/d3tc01187a

J. Mater. Chem. C

2023

DOI: 10.1039/d3tc01187a

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

Xugang Rong

Jueshan Liu

Jianglin Wu

et al.

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...

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2024

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Cited by 4 publications

References 40 publications

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Photo‐Induced Radical Generation of Supramolecular Gel with Sign‐Inverted and White‐Light Circularly Polarized Luminescence

Ji,

Li,

Meng

et al. 2024

Small Methods

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The realization of persistent luminescence and in particular circularly polarized luminescence (CPL) of organic radicals remains a challenge due to their sensitivity to oxygen at ambient conditions and elusive excited state chirality control. Here, it is reported that UV‐irradiation on a supramolecular gel from a chiral triarylamine derivative, TPA‐Ala, led to the formation of luminescent radicals with bright CPL. TPA‐Ala can form an organogel in chloroform with blue emission and supramolecular chirality as demonstrated by both CD and CPL signals. Upon UV 365 nm irradiation, an emission color change from blue to cyan is observed due to the formation of photo‐induced radicals. Interestingly, it is found that the supramolecular gel radicals showed stable luminescence with a lifetime ≈ 10 days in dark environments and inverted CPL, which represents a scarce example with persistent CPL from doublet‐state due to oxygen isolation ability of the gel network. Furthermore, doping a guest dye, Rhodamine B (RhB), into the supramolecular gel (RhB/TPA‐Ala = 30% in molar ratio) successfully obtained a transient white‐light CPL through the superposition of photo‐induced radical and guest dye emissions. This work provides a useful methodology for the fabrication of radical‐based CPL materials via a supramolecular assembly approach.

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Photo‐Induced Radical Generation of Supramolecular Gel with Sign‐Inverted and White‐Light Circularly Polarized Luminescence

Ji,

Li,

Meng

et al. 2024

Small Methods

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Understanding the Key Factors for Photoinduced Radical Generation in Crystalline Triphenylamines Using Experiment and Machine Learning

Wijesekera,

Gbadamosi,

Hossain

et al. 2024

J. Phys. Chem. C

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In this study, we combine experiments, calculated properties, and machine learning (ML) to design new triphenylamine-based (TPA) molecules that have a high photoinduced radical (PIR) generation in crystals. A data set of 34 crystal structures was extracted from the Cambridge Crystallographic Data Centre. Eighteen structures with experimentally reported PIR values from 0 to 0.85% were used to build an ML model trained using Random Forest that achieves an average leave-one-out test set error of 0.173% PIR. The ML model was used to screen the remaining 16 compounds, of which 4 were selected and subsequently compared with the experimentally measured PIR%. The predicted PIR% demonstrated good agreement with the measured values of TPA bis-urea macrocycle host−guest complexes and non-macrocyclic compounds of TPAs. Examining a broad set of molecular architectures/scaffolds allows for investigating the structural and electronic properties that lead to high PIR generation. We found very different trends for macrocycles, linear TPAs, and mono TPAs, where mono TPAs consistently have the lowest PIR generation. Macrocycles tend to have the highest PIR generation, especially for systems with benzene and fluorobenzene guests. Although linear analogs overall perform worse than macrocycles, they display clear trends with increasing excited-state dipole moment, oscillator strength, and electron−hole covariance, while decreasing ionization potential and interatomic distance are generally correlated with higher PIRs. What is consistently observed is that higher PIRs are seen for brominated analogs. Our study, therefore, provides guidelines for future design strategies of TPAs for PIR generation.

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Spin characteristics in conjugated stable diradicals

Dai,

Zhan,

Shi

et al. 2024

Chem. Commun.

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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...

Cited by 4 publications

References 40 publications

Photo‐Induced Radical Generation of Supramolecular Gel with Sign‐Inverted and White‐Light Circularly Polarized Luminescence

Photo‐Induced Radical Generation of Supramolecular Gel with Sign‐Inverted and White‐Light Circularly Polarized Luminescence

Understanding the Key Factors for Photoinduced Radical Generation in Crystalline Triphenylamines Using Experiment and Machine Learning

Spin characteristics in conjugated stable diradicals

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