Free-radical copolymerization of cyclic ketene acetals (CKAs) and vinyl ethers (VEs) was investigated as an efficient yet simple approach for the preparation of functional aliphatic polyesters. The copolymerization of CKA and VE was first predicted to be quasi-ideal by DFT calculations. The theoretical prediction was experimentally confirmed by the copolymerization of 2-methylene-1,3-dioxepane (MDO) and butyl vinyl ether (BVE), leading to r =0.73 and r =1.61. We then illustrated the versatility of this approach by preparing different functional polyesters: 1) copolymers functionalized by fluorescent probes; 2) amphiphilic copolymers grafted with poly(ethylene glycol) (PEG) side chains able to self-assemble into PEGylated nanoparticles; 3) antibacterial films active against Gram-positive and Gram-negative bacteria (including a multiresistant strain); and 4) cross-linked bioelastomers with suitable properties for tissue engineering applications.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201707043 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Direct Stereoselective Synthesis of 2-Deoxyglycosides via Visible-Light-Induced Photoacid-Catalyzed Activation of Glycosyl -[1-(-MeO-Phenyl)vinyl]benzoates (PMPVBs) as Donors.
J Org Chem
January 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, Assam 781039, India.
The photoacid-catalyzed synthesis of 2-deoxy glycosides is presented using stable glycosyl -[1-(-MeO-Phenyl)vinyl]benzoate (PMPVB) donors and employing the eosin Y and diphenyl disulfide (PhSSPh) catalytic system in the presence of blue LED lights. The remote activation of the alkene functionality under the photoacid catalysis followed by a 5-- cyclization led to the generation of oxocarbenium ions that were trapped to provide the glycosylated products in excellent yields and decent selectivities under mild conditions. This method is also useful for the photoacid-catalyzed synthesis of -methoxybenzyl-alkyl ethers.
View Article and Find Full Text PDFSynthesis and Reactivity of an Olefin Metathesis-Catalyzing Ruthenium Complex with a Selenoether Moiety in the Benzylidene Ligand.
ACS Omega
December 2024
Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan.
A Hoveyda-Grubbs (HG)-type olefin metathesis complex with a selenoether moiety at the terminus of phenoxy moiety was synthesized. The complex showed direct selenium-atom coordination to the ruthenium center, resulting in higher thermodynamic stability compared with the parent HG catalyst. The selenium atom binding enhanced the tolerance to protic solvent molecules in ring-closing metathesis of -tosyldiallylamide and diethyl diallylmalonate, and also in the cross metathesis between 3-butenylbenzoate and methyl acrylate.
View Article and Find Full Text PDFPhotocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover.
Angew Chem Int Ed Engl
January 2025
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, CH-1015, Lausanne, Switzerland.
The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range of alkenes, including vinyl arenes, enamides, enol ethers, vinyl sulfides, and dehydroamino esters, were regioselectively functionalized with an azide and nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric acids, oximes, and phenols. The method led to a more efficient synthesis of 1,2-azidofunctionalized pharmaceutical intermediates when compared to previous approaches, resulting in both reduction of step count and increase in overall yield.
View Article and Find Full Text PDFA Flexible Yet Robust 3D-Hybrid Gel Solid-State Electrolyte Based on Metal-Organic Frameworks for Rechargeable Lithium Metal Batteries.
Gels
December 2024
School of Chemistry and Materials Science, Guangdong University of Education, Guangzhou 510303, China.
Compared to traditional liquid electrolytes, solid electrolytes have received widespread attention due to their higher safety. In this work, a vinyl functionalized metal-organic framework porous material (MIL-101(Cr)-NH-Met, noted as MCN-M) is synthesized by postsynthetic modification. A novel three-dimensional hybrid gel composite solid electrolyte (GCSE-P/MCN-M) is successfully prepared via in situ gel reaction of a mixture containing multifunctional hybrid crosslinker (MCN-M), lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), ethylene carbonate (EC), diethylene glycol monomethyl ether methacrylate (EGM) and polyethylene (vinylidene fluoridee) (PVDF).
View Article and Find Full Text PDFAnaerobic plasmalogen production in recombinant Escherichia coli carrying plasmalogen synthase gene from Selenomonas ruminantium.
Biosci Biotechnol Biochem
December 2024
Department of Agricultural Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Miyagi, Japan.
Escherichia coli expressing SrPlsAR from Selenomonas ruminantium produces plasmalogen, comprising almost 60% of the total phospholipid content under anaerobic conditions. Both plasmenylethanolamine and plasmenylglycerol were detected, and the major acyl aldehyde derived from sn-1 vinyl ether was C16:1. Plasmalogen synthesis is affected by mutations in ATP-binding sites and Cys expected to be involved in the formation of the [4Fe-4S] cluster.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!