A New One-Pot Synthetic Method
for Selenium-Containing Medium-Sized α,β-Unsaturated
Cyclic Ketones

Sashida, Haruki; Nakayama, Akemi; Kaname, Mamoru

doi:10.1055/s-0028-1083153

Cited by 31 publications

(18 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Prior to use, acrylic acid (98%; Energy Chemical, Shanghai, China), 2-hydroxyethyl methacrylate (HEMA, 96%; Energy Chemical, Shanghai, China), and acrylchloride (AR; Macklin, Shanghai, China) were purified by passage through an Al 2 O 3 column to remove inhibitors. γ-Selenobutyrolactone was synthesized according to a previously reported method [39]. 4-(1,2,2-Triphenylvinyl)phenyl acrylate (TPE-a) was synthesized according to a previously reported method [22].…”

Section: Methodsmentioning

confidence: 99%

Novel AIEgen-Functionalized Diselenide-Crosslinked Polymer Gels as Fluorescent Probes and Drug Release Carriers

et al. 2020

View full text Add to dashboard Cite

Stimuli-responsive functional gels have shown significant potential for application in biosensing and drug release systems. In this study, aggregation-induced emission luminogen (AIEgen)-functionalized, diselenide-crosslinked polymer gels were synthesized via free radical copolymerization. A series of polymer gels with different crosslink densities or tetraphenylethylene (TPE) contents were synthesized. The diselenide crosslinker in the gels could be fragmented in the presence of H2O2 or dithiothreitol (DTT) due to its redox-responsive property. Thus, the TPE-containing polymer chains were released into the aqueous solution. As a result, the aqueous solution exhibited enhanced fluorescence emission due to the strong hydrophobicity of TPE. The degradation of polymer gels and fluorescence enhancement in an aqueous solution under different H2O2 or DTT concentrations were studied. Furthermore, the polymer gels could be used as drug carriers, suggesting a visual drug release process under the action of external redox agents. The AIEgen-functionalized, diselenide-crosslinked polymer gels hold great potential in the biomedical area for biosensing and controlled drug delivery.

show abstract

Section: Methodsmentioning

confidence: 99%

Novel AIEgen-Functionalized Diselenide-Crosslinked Polymer Gels as Fluorescent Probes and Drug Release Carriers

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Tetrabutylammonium hydrogen sulfate (Bu 4 NHSO 4 ) was provided from TCI (Shanghai, China). γ-Butyroselenolactone was prepared according to reference [33]. Other chemicals were purchased from Shanghai Regant Co. Ltd. China and used without treatment.…”

Section: Methodsmentioning

confidence: 99%

Recyclable Self-Healing Polyurethane Cross-Linked by Alkyl Diselenide with Enhanced Mechanical Properties

Qian

Huang

et al. 2019

Polymers

View full text Add to dashboard Cite

Dynamic structures containing polymers can behave as thermosets at room temperature while maintaining good mechanical properties, showing good reprocessability, repairability, and recyclability. In this work, alkyl diselenide is effectively used as a dynamic cross-linker for the design of self-healing poly(urea–urethane) elastomers, which show quantitative healing efficiency at room temperature, without the need for any catalysts or external interventions. Due to the combined action of the urea bond and amide bond, the material has better mechanical properties. We also compared the self-healing effect of alkyl diselenide-based polyurethanes and alkyl disulfide-based polyurethanes. The alkyl diselenide has been incorporated into polyurethane networks using a para-substituted amine diphenyl alkyl diselenide. The resulting materials not only exhibit faster self-healing properties than the corresponding disulfide-based materials, but also show the ability to be processed at temperatures as low as 60 °C.

show abstract

“…9 Herein, we aimed for the in situ selenol generation, through a one-pot amine−oxidation coupling, which can serve as a new, quite versatile, and powerful protocol for the synthesis of diselenide-containing polymers with various architectures. In our methodology, selenolactone, which is the key precursor of selenol, is easily synthesized from sodium hydrogen selenide (NaHSe) on a multigram scale, 10 while the corresponding polymerizations with different commercial diamines are atom efficient, simple, and fast (Scheme 1).…”

mentioning

confidence: 99%

Selenolactone as a Building Block toward Dynamic Diselenide-Containing Polymer Architectures with Controllable Topology

et al. 2017

View full text Add to dashboard Cite

A versatile protocol for the synthesis of a variety of multiresponsive diselenide-containing polymeric architectures was investigated. It consists of a one-pot, two-step process with the generation of a selenol by in situ nucleophilic ring opening of selenolactone with a broad range of amine-containing structures, followed by the transformation of the obtained compounds to the corresponding diselenide through a spontaneous oxidation coupling reaction. After elaboration of this one-pot reaction, a number of routes based on selenolactones have been developed for the successful synthesis of functional, linear, branched, cyclic, and cross-linked polymers via a mild, straightforward process. Moreover, the polymer end groups can be easily modified by changing the ratio of amine and selenolactone or sequential Michael addition of selenol to the methacrylic ester. At last, the self-healing properties of the diselenide-containing networks were determined by exposing a cut sample of the polymer to UV light.

show abstract

A New One-Pot Synthetic Method for Selenium-Containing Medium-Sized α,β-Unsaturated Cyclic Ketones

Cited by 31 publications

References 3 publications

Novel AIEgen-Functionalized Diselenide-Crosslinked Polymer Gels as Fluorescent Probes and Drug Release Carriers

Novel AIEgen-Functionalized Diselenide-Crosslinked Polymer Gels as Fluorescent Probes and Drug Release Carriers

Recyclable Self-Healing Polyurethane Cross-Linked by Alkyl Diselenide with Enhanced Mechanical Properties

Selenolactone as a Building Block toward Dynamic Diselenide-Containing Polymer Architectures with Controllable Topology

Contact Info

Product

Resources

About