Photoexcited perylene diimide radical anions for the reduction of aryl halides: a bay-substituent effect

Gong, Hai-Xian; Cao, Zhu; Li, Menghua; Liao, Saihu; Lin, Mei‐Jin

doi:10.1039/c8qo00445e

Cited by 60 publications

(49 citation statements)

References 42 publications

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“…Hence, the copolymer has better electrochemical activity than homopolymer of ANi, which is consistent with the literature . According to the previous literatures, the electron‐withdrawing group can replace the hydrogen on the benzene ring, and the density of electron cloud on the benzene ring decreases, resulting in electron withdrawing effect which can enhance the electrical activity of the copolymer backbone. So these results mainly because that the nitro of o ‐nitroaniline is one of electron‐withdrawing groups.…”

Section: Resultssupporting

confidence: 89%

Electrosynthesis and characterizations of a multielectrochromic copolymer based on aniline and o‐nitroaniline in visible‐infrared region

Zhang

et al. 2018

J of Applied Polymer Sci

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An IR electrochromic film constructed by copolymer of aniline and o‐nitroaniline has been successfully prepared by cyclic voltammetry. The effects of polymerization of aniline and o‐nitroaniline on electrochromic properties and optical properties were investigated by cyclic voltammetry, scanning electron microscopy, FTIR spectrometer, and UV–vis spectrophotometer. The results indicate that the film can exhibit three colors (apple green, dark green, and dark blue) at different voltages of −0.1, 0, and 0.8 V. Simultaneously, a fast response time (1.89 and 4.47 s), a high coloration efficiency, a significant optical modulation (60% between −0.1 and 0.8 V) and a large average emissivity range (Δεmax = 0.203) are achieved for the new film. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47290.

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Section: Resultssupporting

confidence: 89%

Electrosynthesis and characterizations of a multielectrochromic copolymer based on aniline and o‐nitroaniline in visible‐infrared region

Zhang

et al. 2018

J of Applied Polymer Sci

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“…The results of this section clearly demonstrate that increasing the thermodynamic reactivity of a catalytic system while maintaining a long lifetime, i.e., a high kinetic reactivity, of the initiating species (longer than 1 microsecond, see Scheme 1) is very benecial for photoredox applications: rst, we introduced the light intensity as selectivity parameter to reductive photoredox activations; second, our approach relying on e aq c À as superreductant ensures relatively short reaction times for challenging and consecutive photoreactions, which otherwise frequently require more than one day of intense photoirradiation. 15,35,37 2.2 From triplet-triplet energy transfer (TTET) to electron transfer (ET) chemistry…”

Section: Redox-potential Control For Reductive Dehalogenationsmentioning

confidence: 99%

Reactivity control of a photocatalytic system by changing the light intensity

Kerzig

Wenger

2019

Chem. Sci.

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“…Naphthalene diimides (NDIs) as the smallest possible rylene dyes are such an important class of organic dyes. In contrast to their bigger homologs perylene diimides which were rarely used for photoredox catalysis [32–34], NDIs have a lower tendency to self-aggregate due to their smaller aromatic surface and thus are slightly better soluble in organic solvents [35–38]. NDIs are intensively applied as functional dyes [39–40], for artificial photosynthesis [41–42], for molecular architectures by self-assembly [43–44], as molecular sensors [45–47] and for organic electronics [48–49], but yet nearly completely unexplored for photoredox catalysis.…”

Section: Introductionmentioning

confidence: 99%

Naphthalene diimides with improved solubility for visible light photoredox catalysis

Reiß

Wagenknecht

2019

Beilstein J. Org. Chem.

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Five core-substituted naphthalene diimides bearing two dialkylamino groups were synthesized as potential visible light photoredox catalysts and characterized by methods of optical spectroscopy and electrochemistry in comparison with one unsubstituted naphthalene diimide as reference. The core-substituted naphthalene diimides differ by the alkyl groups at the imide nitrogens and at the nitrogens of the two substituents at the core in order to enhance their solubility in DMF and thereby enhance their photoredox catalytic potential. The 1-ethylpropyl group as rather short and branched alkyl substituent at the imide nitrogen and the n-propyl group as short and unbranched one at the core amines yielded the best solubilities. The electron-donating diaminoalkyl substituents together with the electron-deficient aromatic core of the naphthalene diimides increase the charge-transfer character of their photoexcited states and thus shift their absorption into the visible light (500–650 nm). The excited state reduction potential was estimated to be approximately +1.0 V (vs SCE) which is sufficient to photocatalyze typical organic reactions. The photoredox catalytic activity in the visible light range was tested by the α-alkylation of 1-octanal as benchmark reaction. Irradiations were performed with LEDs in the visible light range between 520 nm and 640 nm. The irradiation by visible light together with the use of an organic dye instead of a transition metal complex as photoredox catalyst improve the sustainability and make photoredox catalysis “greener”.

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Photoexcited perylene diimide radical anions for the reduction of aryl halides: a bay-substituent effect

Abstract: Photoexcited perylene diimide radical anions exhibit remarkable substituent-dependent photocatalytic activities towards the reduction of aryl halides, which are mainly controlled by their excited-state reduction potentials and SOMO−1 energies.

Cited by 60 publications

References 42 publications

Electrosynthesis and characterizations of a multielectrochromic copolymer based on aniline and o‐nitroaniline in visible‐infrared region

Electrosynthesis and characterizations of a multielectrochromic copolymer based on aniline and o‐nitroaniline in visible‐infrared region

Reactivity control of a photocatalytic system by changing the light intensity

Naphthalene diimides with improved solubility for visible light photoredox catalysis

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