Indeno[2,1‐a]fluorene‐11,12‐dione Radical Anions: Synthesis, Characterization, and Properties

Wang, Jie; Ruan, Huapeng; Hu, Zhao‐Bo; Wang, Wenqing; Zhao, Yue; Wang, Xinping

doi:10.1002/chem.202103897

Cited by 5 publications

(2 citation statements)

References 75 publications

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“…(ii) The bonds in the hmtt ligand also showed variations in length, which meant that they were also involved in the photochromism. (iii) While we cannot be certain which fraction of the ligands in these MOFs undergo a change, the bond length modifications in these MOFs are consistent with those reported for organic pyrene-fused azaacene and indeno[2,1- a ]fluorene-11,12-dione radical anions and N , N′ -diphenyldihydrophenazine radical cations. − …”

Section: Resultsmentioning

confidence: 99%

Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

et al. 2022

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Metal−organic frameworks (MOFs) can respond to light in a number of interesting ways. Photochromism is observed when a structural change to the framework is induced by the absorption of light, which results in a color change. In this work, we show that introducing quinoxaline ligands to MUF-7 and MUF-77 (MUF = Massey University Framework) produces photochromic MOFs that change color from yellow to red upon the absorption of 405 nm light. This photochromism is observed only when the quinoxaline units are incorporated into the framework and not for the standalone ligands in the solid state. Electron paramagnetic resonance (EPR) spectroscopy shows that organic radicals form upon irradiation of the MOFs. The EPR signal intensities and longevity depend on the precise structural details of the ligand and framework. The photogenerated radicals are stable for long periods in the dark but can be switched back to the diamagnetic state by exposure to visible light. Single-crystal X-ray diffraction analysis reveals bond length changes upon irradiation that are consistent with electron transfer. The multicomponent nature of these frameworks allows the photochromism to emerge by allowing through-space electron transfer, precisely positioning the framework building blocks, and tolerating functional group modifications to the ligands.

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Section: Resultsmentioning

confidence: 99%

Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

et al. 2022

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“…23 Previous reports have shown that introducing nitrogen atoms or electron-withdrawing groups into the polycyclic aromatic hydrocarbon (PAH) aids in the formation of stable radical anions. [24][25][26][27][28][29][30][31][32] It is well known that spin delocalization can improve the stability of radical anions, particularly for large planar structures, such as PAHs, due to the conjugation effects. In addition, the dimerization reaction of two bowlshaped PAH monoanion radicals was first reported in 2018 by the Petrukhina and Rogachev groups.…”

Section: Introductionmentioning

confidence: 99%

Antiaromaticity-promoted radical anion stability in α-vinyl heterocyclics

Lin

Zhu

2022

Org. Chem. Front.

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α‐Cyano Triaryl[3]radialene: Unsymmetrical Stereo‐configuration, Clustering‐enhanced Excimer Emission, and Radical‐involved Multimodal Information Switching

Liu

Zhou

et al. 2023

Angewandte Chemie

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3]Radialene has a peculiar topology and cross-conjugation system, representing a unique molecular scaffold in organic materials. Herein, we report a special class of stereoisomeric α-cyano triaryl-[3]radialenes (CTRs) that show concentration-caused quenching in solution but emit red-shifted and enhanced luminescence in the crystalline state. Clustering of multiple cyano groups and their through-space interactions with the [3]radialene ring significantly extend π-electron communication meanwhile rigidifying the propeller conformation multivalently, thus playing a key role behind the state-dependent luminescence. These radialenes with a substantial electron affinity undergo a reversible electron transfer transition to anionic radicals with good stability, showing switching of photoabsorption, photoluminescence and electron spin resonance (ESR) signal. We also established proof-of-concept applications of CTRs for multimodal information encryption and chemical sensing.

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Indeno[2,1‐a]fluorene‐11,12‐dione Radical Anions: Synthesis, Characterization, and Properties

Cited by 5 publications

References 75 publications

Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

Antiaromaticity-promoted radical anion stability in α-vinyl heterocyclics

α‐Cyano Triaryl[3]radialene: Unsymmetrical Stereo‐configuration, Clustering‐enhanced Excimer Emission, and Radical‐involved Multimodal Information Switching

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