An electron-deficient MOF as an efficient electron-transfer catalyst for selective oxidative carbon–carbon coupling of 2,6-di-<i>tert</i>-butylphenol

Liu, Teng; Shen, Xianfu; Liu, Zhengfen; Zhang, Feng; Liu, Jian‐Jun

doi:10.1039/d2dt00869f

Cited by 6 publications

(1 citation statement)

References 61 publications

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“…Polyoxometalates (POMs), a class of anionic metal oxide clusters with oxygen-rich surfaces, are good photoactive electron reservoirs; they can potentially undergo photoinduced electron-or proton-transfer processes, which can be used to fabricate donor-acceptor hybrid materials with electron-deficient PDIs through unusual anion-π interactions. [44][45][46][47][48] Our and other groups have synthesized a series of photoactive hybrids based on POMs and functional organic ligands by taking advantage of noncovalent interactions, [49][50][51][52][53][54] but the application of these systems in promoting organic transformations has not yet been explored. Herein, we prepared a series of extremely rare radical-doped donor-acceptor hybrid materials, namely Cl (4), based on electron-deficient PDI and Keggin-type POM anions; they exhibited fast-responsive reversible photochromism and reactive organic radicals under ambient conditions, which resulted from the interactions of PDI radical anions and POMs (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Polyoxometalate‐dependent Photocatalytic Activity of Radical‐doped Perylenediimide‐based Hybrid Materials

Dai,

Li,

et al. 2024

Chemistry A European J

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Four radical‐doped PDI‐based crystalline hybrid materials, Cl4‐PDI·SiW12O40 (1), Cl4‐PDI·SiMo12O40 (2), Cl4‐PDI·PW12O40 (3), and Cl4‐PDI·PMo12O40 (4), were attainedby slow diffusion of polyoxometalates (POMs) into acidified Cl4‐PDI solutions. The obtained PDI‐based crystalline hybrid materials not only exhibited prominent photochromism, but also possessed reactive organic radicals under ambient conditions. Furthermore, all hybrid materials could be easily photoreduced to their radical anions (Cl4‐PDI•‒), and then underwent a second photoexcitation to form energetic excited state radical anions (Cl4‐PDI•‒*). However, experiments and theoretical calculations demonstrated that the formed energetic Cl4‐PDI•‒* showed unusual POM‐dependent photocatalytic efficiencies toward the oxidative coupling of amines and the iodoperfluoroalkylation of alkenes; higher photocatalytic efficiencies were found for hybrid materials 1 and 2 compared to 3 and 4. The photocatalytic efficiencies of these hybrid materials are mainly controlled by the energy differences between the SOMO‐2 level of Cl4‐PDI•‒* and the LUMO level of the POMs.

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Section: Introductionmentioning

confidence: 99%

Polyoxometalate‐dependent Photocatalytic Activity of Radical‐doped Perylenediimide‐based Hybrid Materials

Dai,

Li,

et al. 2024

Chemistry A European J

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Deprotonation‐Induced Color Modulation in N,N′‐Dihydroxynaphthalenediimide‐Based Organic Crystals

et al. 2023

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N,N’‐dihydroxy‐1,4,5,8‐naphthalenetetracarboxdiimide (NDI−(OH)2) has attracted much attention in recent years, because its doubly deprotonated state, (O−NDI−O)2−, has metal‐coordination ability and characteristic electronic transition useful for designing electronic and optical functions. In contrast, a molecular crystal with the mono‐deprotonated (HO−NDI−O)− ion remains unknown. We herein report an organic crystal containing non‐disproportionated (HO−NDI−O)− ions, which are connected by very strong O−H−O hydrogen bonds. Its lowest energy absorption band (450 to 650 nm) is observed in between that of NDI−(OH)2 (380 nm) and isolated (O−NDI−O)2− (500 to 850 nm) species, consistent with the molecular orbital calculations. This absorption originates from the electronic transition from deprotonated imide‐based orbitals to NDI‐core orbitals, which can be influenced by the hydrogen bonds around imide group. Consequently, the optical properties of NDI−(OH)2 can be modulated by the stepwise deprotonation and hydrogen‐bonding interactions.

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Two photochromic two-dimensional Zn(II)-MOFs based on a carboxybenzyl viologen ligand

Chen,

Fu,

Shen

et al. 2024

Dyes and Pigments

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An electron-deficient MOF as an efficient electron-transfer catalyst for selective oxidative carbon–carbon coupling of 2,6-di-tert-butylphenol

Abstract: An electron-deficient MOF based on the NDI derivative has been developed for selective oxidative C–C coupling of 2, 6-di-tert-butylphenol to different products by controlling the reaction conditions.

Cited by 6 publications

References 61 publications

Polyoxometalate‐dependent Photocatalytic Activity of Radical‐doped Perylenediimide‐based Hybrid Materials

Polyoxometalate‐dependent Photocatalytic Activity of Radical‐doped Perylenediimide‐based Hybrid Materials

Deprotonation‐Induced Color Modulation in N,N′‐Dihydroxynaphthalenediimide‐Based Organic Crystals

Two photochromic two-dimensional Zn(II)-MOFs based on a carboxybenzyl viologen ligand

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