Self anion radical induced breaking carbon–oxygen bond in bay area of perylene diimide, and nucleophilic substitution with SRN1 mechanism

Tetrahedron ◽  
2021 ◽  
pp. 132480
Author(s):  
Yuzhen Zhao ◽  
Zemin He ◽  
Yang Zhao ◽  
Zhun Guo ◽  
Huimin Zhang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Anion Radical ◽  
Perylene Diimide ◽  
Bay Area ◽  
Oxygen Bond

Ambient stable perylene diimide anion radical for high conductivity and potential application as chemiresistive sensor

2020 ◽  
Vol ahead-of-print (ahead-of-print) ◽  
Author(s):  
Yuzhen Zhao ◽  
Yang Zhao ◽  
Xiaoxi Kang ◽  
Zongcheng Miao ◽  
Haiquan Zhang
Keyword(s):  
Thin Film ◽  
Acetic Acid ◽  
Electronic Properties ◽  
Potential Application ◽  
Anion Radical ◽  
Organic Molecules ◽  
Perylene Diimide ◽  
Interdigitated Electrodes ◽  
Content Type ◽  
Perylene Diimide Derivatives

Purpose This paper aims to compare the electronic properties of perylene diimide derivatives (DFPDI) and its anion radical (DFPDI.-k.+) thin film by drop-coating of organic molecules on the interdigitated electrodes. Design/methodology/approach The authors compared the electronic properties of perylene diimide derivatives and its anion radical by drop-coating of organic molecules on interdigitated electrodes. Significantly, the current of perylene diimide derivatives anion radical increased by 2∼3 orders of magnitude compared to perylene diimide derivatives under a bias of 5 V, and the maximal current of anion radical that from tetrahydrofuran solution can reach 3.6 mA. Furthermore, DFPDI.-k.+ thin film showed time-resistance sensitivity for acetic acid. When DFPDI.-k.+ thin film was placed in acetic acid of 3.1 × 105 ppm, the current was decreased 46 times under a bias of 6 V after 8 min. Findings We developed the new method to prepare ambient stable perylene diimide derivatives anion radical, which shows sensitivity of absorption spectra to acid. Originality/value Perylene diimide derivatives anion radical thin film showed time-resistance sensitivity for acetic acid, suggesting potential application of perylene diimide derivatives anion radical as acid sensor.

Predicting Solvent Stability in Aprotic Electrolyte Li–Air Batteries: Nucleophilic Substitution by the Superoxide Anion Radical (O2•–)

2011 ◽  
Vol 115 (44) ◽  
pp. 12399-12409 ◽  
Author(s):  
Vyacheslav S. Bryantsev ◽  
Vincent Giordani ◽  
Wesley Walker ◽  
Mario Blanco ◽  
Strahinja Zecevic ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Superoxide Anion ◽  
Anion Radical ◽  
Superoxide Anion Radical ◽  
Solvent Stability ◽  
Aprotic Electrolyte

Nucleophilic substitution reactions in m-nitrobenzylic substrates

1983 ◽  
Vol 36 (1) ◽  
pp. 81 ◽  
Author(s):  
SD Barker ◽  
RK Norris
Keyword(s):  
Nucleophilic Substitution ◽  
Radical Anion ◽  
Anion Radical ◽  
The Other ◽  
Radical Anions ◽  
Malonic Ester ◽  
Mechanism Of Formation ◽  
Substitution Reactions ◽  
Radical Process ◽  
Rule Out

The reaction of m-nitrobenzyl 2,4,6-trimethylbenzoate (11) with the salt (2) of 2-nitropropane, or the thiolate (16), gives moderate yields of substitution products [e.g.(3) or (17)]. However, the mechanism of formation of these products could not be definitively assigned. The m-nitrobenzyl chloride (12), on the other hand, was clearly demonstrated to undergo SRN1 substitution reactions with a variety of anions including the anion from the salt (2), thiolate ion from (16), azide from (22), the malononitrile anion from (20), and the malonic ester anion from (21). Inhibition and entrainment effects clearly rule out an alternative radical anion-radical process involving cage collapse. The occurrence of SRNl reactions in m-nitrobenzylic substrates adds support to a mechanism involving association of radicals with anions, and for dissociation of radical anions, which involves σ* and π* radical anions.

Practical Preparation of Octa- and Tetrabromoperylene Diimides and Derivatives Thereof

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5176-5182 ◽  
Author(s):  
Augustina Jozeliūnaitė ◽  
Romualdas Striela ◽  
Linas Labanauskas ◽  
Edvinas Orentas
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrazine Hydrate ◽  
Perylene Diimide ◽  
Partial Reduction ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
One Step ◽  
Perylene Diimide Derivatives

A mild synthesis of fully brominated perylene dianhydride and diimides in one step from easily available unsubstituted precursors is presented. The partial reduction of ortho-bromo substituents with hydrazine hydrate allowed for a gram-scale synthesis of a valuable intermediate, 1,6,7,12-tetrabromoperylene diimide. Several new twisted fully core-substituted perylene diimide derivatives having sulfur, nitrogen, or oxygen substituents were synthesized using regioselective nucleophilic substitution reactions.

scholarly journals Reactive bay functionalized perylene monoimide-polyhedral oligomeric silsesquioxane organic electronic dye

2015 ◽  
Vol 33 (1) ◽  
pp. 113-121 ◽  
Author(s):  
Lodrick Makokha Wangatia ◽  
Bin Sun ◽  
Ting Zeng ◽  
Meifang Zhu
Keyword(s):  
Solid State ◽  
Photophysical Properties ◽  
Polyhedral Oligomeric Silsesquioxane ◽  
Perylene Diimide ◽  
Spherical Particles ◽  
High Tech ◽  
Polyhedral Oligomeric Silsesquioxanes ◽  
Bay Area ◽  
Solid Fluorescence ◽  
Oligomeric Silsesquioxane

AbstractAggregation-induced quenching is particularly detrimental in perylene diimides, which are characterized by a near-unity fluorescence quantum yield in solution but are far less emissive in the solid state. Previously, perylene diimide has been improved by linking it to the inorganic cage of polyhedral oligomeric silsesquioxanes. As a further study on perylene diimidepolyhedral oligomeric silsesquioxanes, we report on a double functionalized molecular structure, which can be used for substitution at the bay area and as a side group in other materials. Typical solution absorption and emission features of the perylene diimide fragment have been observed in this new reactive perylene diimide-polyhedral oligomeric silsesquioxane. Moreover, reduced stacking during aggregation and spherical particles exhibiting solid fluorescence have been obtained. Organic semiconducting material with enhanced solid state photophysical properties, like solid fluorescence is a subject of great interest owing to its possible high-tech applications in optoelectronic devices.

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