133689-52-8Relevant academic research and scientific papers
Naphthalene diimide templated synthesis of pillar[6]arenes
Ke, Hua,Jiao, Chen,Qian, Yu-Heng,Lin, Mei-Jin,Chen, Jian-Zhong
, p. 339 - 342 (2015)
A facile method for the selective synthesis of pillar[6]arenes has been developed. Due to a strong electron donor-acceptor interaction between the electron-deficient naphthalene diimide and a precursor for the pillararene, 1,4-diisobutoxy-2,5-bis(methoxym
Electrochemical and structural investigation of the interactions between naphthalene diimides and metal cations
Reiner, Benjamin R.,Foxman, Bruce M.,Wade, Casey R.
, p. 9472 - 9480 (2017)
The effects of Li+ and Mg2+ on the electrochemical behaviour and photoreduction of N,N′-bis(2,6-diisopropylphenyl)naphthalene diimide (Dipp2NDI) have been investigated using cyclic voltammetry and UV-vis spectroscopy. Strong cation-anion interactions between Li+ or Mg2+ and [Dipp2NDI]2- result in solvent-dependent anodic shifts of the NDI-/2- redox couple. In organic solvents of moderate dielectric constant and donor ability, the two, one-electron redox processes typically observed for Dipp2NDI merge into a single, two-electron process. This strong metal cation effect has been leveraged for the photoreduction of Dipp2NDI to [Dipp2NDI]2-via a disproportionation process. Chemical reduction of Dipp2NDI with iPrMgCl has allowed the isolation of Mg2+ complexes of [Dipp2NDI]2-. Single crystal X-ray diffraction was used to determine the structure of a dimeric complex, [(Dipp2NDI)Mg2(THF)3]2, that features strong coordination of Mg2+ by the oxygen atoms of the reduced NDI.
On the Reaction of Naphthalene Diimides with Fluoride Ions: Acid/Base versus Redox Reactions
Bélanger-Chabot, Guillaume,Ali, Ahmed,Gabba?, Fran?ois P.
, p. 9958 - 9961 (2017)
The characterization of a naphthalene diimide (NDI) radical anion is presented. Its properties allow a reliable comparison point for other systems involving the NDI radical anion, such as systems claimed to perform the oxidation of the fluoride anion. In addition to reiterating the obvious thermodynamic objections to such an unlikely oxidation, we present several observations that show that the fluoride anion does not act as a one-electron reducing agent toward the NDI investigated in this work.
Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**
Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.
supporting information, p. 21418 - 21425 (2021/08/25)
Herein, we disclose that electrochemical stimulation induces new photocatalytic activity from a range of structurally diverse conventional photocatalysts. These studies uncover a new electron-primed photoredox catalyst capable of promoting the reductive cleavage of strong C(sp2)?N and C(sp2)?O bonds. We illustrate several examples of the synthetic utility of these deeply reducing but otherwise safe and mild catalytic conditions. Finally, we employ electrochemical current measurements to perform a reaction progress kinetic analysis. This technique reveals that the improved activity of this new system is a consequence of an enhanced catalyst stability profile.
Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling
Chernowsky, Colleen P.,Cowper, Nicholas G. W.,Wickens, Zachary K.,Williams, Oliver P.
supporting information, (2020/02/04)
We describe a new catalytic strategy to transcend the energetic limitations of visible light by electrochemically priming a photocatalyst prior to excitation. This new catalytic system is able to productively engage aryl chlorides with reduction potentials hundreds of millivolts beyond the potential of Na0 in productive radical coupling reactions. The aryl radicals produced via this strategy can be leveraged for both carbon-carbon and carbon-heteroatom bond-forming reactions. Through direct comparison, we illustrate the reactivity and selectivity advantages of this approach relative to electrolysis and photoredox catalysis.
N and P active materials for organic photoelectric conversion layers in organic photodiodes
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Paragraph 0047; 0807-0811, (2018/01/14)
The invention relates to the field of active materials for organic image sensors. The present invention relates to transparent N materials and/or to transparent P materials and their use in absorptionlayer(s), photoelectric conversion layer(s) and/or an o
Pure organic room-temperature phosphorescent material, preparation method thereof and application thereof
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Paragraph 0084; 0085; 0086; 0099-0101, (2017/08/28)
The invention provides a pure organic room-temperature phosphorescent material with a structure as shown in formula (I) or formula (II), and also provides a preparation method for the pure organic room-temperature phosphorescent material with the structure as shown in formula (I) or formula (II). The invention discloses a series of pure organic room-temperature phosphorescent materials based on a naphthalimide derivative. The pure organic room-temperature phosphorescent materials are characterized in that pure organic electron-donating groups are introduced into molecules, so that the molecules are excited by an outside light source to generate a charge transfer state (ICT) in the molecules, and ICT can promote intersystem crossing, so that generation of room-temperature phosphorescence is facilitated. The pure organic phosphorescent material provided by the invention has the advantages of being simple and convenient to synthesize, low in cost, easy to chemically modify, low in toxicity, environmentally friendly and the like.
π-Extended rigid triptycene-trisaroylenimidazoles as electron acceptors
Menke, Elisabeth H.,Lami, Vincent,Vaynzof, Yana,Mastalerz, Michael
supporting information, p. 1048 - 1051 (2016/01/20)
Two soluble isomeric acceptor molecules based on a triptycene core, which is connected to three aroylenimidazole units are described. Due to the inherent threefold axis, the molecules are soluble and thus could be fully photophysically characterized in so
Electron-deficient naphthalene diimides as efficient planar π-acid organocatalysts for selective oxidative C-C coupling of 2,6-di-tert-butylphenol: A temperature effect
Ke, Hua,Wang, Li,Chen, Yong,Lin, Mei-Jin,Chen, Jian-Zhong
, p. 26 - 30 (2014/03/21)
An efficient planar π-acid electron transfer organocatalyst based on electron-deficient substituted naphthalene diimide has been developed for oxidative C-C coupling of 2,6-di-tert-butylphenol to its dimeric derivative or unexpected ring-rearranged trimeric quinone methide by controlling the reaction temperatures.
N-Alkylated and N,N-dialkylated 1,6-diaminoperylene diimides synthesized via copper catalyzed direct aromatic amination
Rauch, Gesche,H?ger, Sigurd
supporting information, p. 5659 - 5661 (2014/05/20)
Perylene diimides (PDIs) and naphthalene diimides (NDIs) can be efficiently aminated with primary or secondary amines under mild conditions using Cu(ii) salts as catalysts and air as an oxidant. Depending on the substrate and the amine, yields over 80% ca
