ChemInform Abstract: Microwaves and Aqueous Solvents Promote the Reaction of Poorly Nucleophilic Anilines with a Zincke Salt.

Zeghbib, Narimane; Thelliere, Paul; Rivard, Michaël; Martens, Thierry

doi:10.1002/chin.201634148

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“…On the other hand, the reaction may remain under kinetic control but simply proceed with increased yield that, in itself, leads to larger sheets that crystallize. 35 We also found that MW irradiation accelerates reaction rates and seems to enhance the crystallinity of the products. 36 The gel did not form in ethanol:water (1:1, v:v) under ST conditions.…”

Section: ■ Introductionmentioning

confidence: 59%

“…In two typical reactions, 0.175 g (0.5 mmol) of TAPB and 0.280 g (0.5 mmol) of BDB were mixed and heated for 3 days under ST conditions or for 2 h under MW irradiation. A 4:1 EtOH:H 2 O mixture was shown by Rivard et al 35 to be an optimal solvent for Zincke reactions. Water was found to play an important role in minimizing degradation of the Zincke salt.…”

Section: ■ Introductionmentioning

confidence: 99%

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Viologen-Based Conjugated Covalent Organic Networks via Zincke Reaction

et al. 2017

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Morphology influences the functionality of covalent organic networks and determines potential applications. Here, we report for the first time the use of Zincke reaction to fabricate, under either solvothermal or microwave conditions, a viologen-linked covalent organic network in the form of hollow particles or nanosheets. The synthesized materials are stable in acidic, neutral, and basic aqueous solutions. Under basic conditions, the neutral network assumes radical cationic character without decomposing or changing structure. Solvent polarity and heating method determine product morphology. Depending upon solvent polarity, the resulting polymeric network forms either uniform self-templated hollow spheres (HS) or hollow tubes (HT). The spheres develop via an inside-out Ostwald ripening mechanism. Interestingly, microwave conditions and certain solvent polarities result in the formation of a robust covalent organic gel framework (COGF) that is organized in nanosheets stacked several layers thick. In the gel phase, the nanosheets are crystalline and form honeycomb lattices. The use of the Zincke reaction has previously been limited to the synthesis of small viologen molecules and conjugated viologen oligomers. Its application here expands the repertoire of tools for the fabrication of covalent organic networks (which are usually prepared by dynamic covalent chemistry) and for the synthesis of viologen-based materials. All three materials-HT, HS, and COGF-serve as efficient adsorbents of iodine due to the presence of the cationic viologen linker and, in the cases of HT and HS, permanent porosity.

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Section: ■ Introductionmentioning

confidence: 59%

Section: ■ Introductionmentioning

confidence: 99%