Rhodanine-based Knoevenagel reaction and ring-opening polymerization for efficiently constructing multicyclic polymers.

Nature Communications
Ze ZhangYe-Zi You

Abstract

Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five-membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine-based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.

References

Sep 21, 2002·Science·Christopher W BielawskiRobert H Grubbs
Mar 18, 2006·Science·David J Craik
Mar 30, 2006·Journal of the American Chemical Society·Boyd A Laurent, Scott M Grayson
Nov 7, 2007·Angewandte Chemie·Bruno BulicHerbert Waldmann
Dec 17, 2008·Physical Chemistry Chemical Physics : PCCP·Tannia MarinadoAnders Hagfeldt
Jan 23, 2009·Journal of the American Chemical Society·Zhishen GeShiyong Liu
Mar 5, 2009·Journal of the American Chemical Society·Norased NasongklaFrancis C Szoka
Apr 2, 2009·Journal of the American Chemical Society·Andrew J BoydstonRobert H Grubbs
Jul 23, 2009·Chemical Society Reviews·Boyd A Laurent, Scott M Grayson
Dec 7, 2010·Angewandte Chemie·Christopher Barner-KowollikWim Van Camp
Mar 1, 2011·Journal of the American Chemical Society·Ke ZhangGregory N Tew
May 19, 2011·Angewandte Chemie·Yan XiaRobert H Grubbs
May 28, 2011·Angewandte Chemie·Eun Ji ShinRobert M Waymouth
May 23, 2012·Expert Opinion on Drug Discovery·Tihomir Tomašić, Lucija Peterlin Mašič
Sep 20, 2012·Journal of the American Chemical Society·Jiaoyan ZhouYongsheng Chen
Dec 21, 2012·The Journal of Organic Chemistry·Jeremy J ClemensDean Stamos
Mar 5, 2013·Journal of the American Chemical Society·In-Hwan LeeTae-Lim Choi
May 25, 2013·Journal of the American Chemical Society·Jiaoyan ZhouYongsheng Chen
Apr 16, 2014·Chemical Society Reviews·Rongrong HuBen Zhong Tang
Dec 30, 2014·Journal of the American Chemical Society·Sarah HollidayIain McCulloch
Dec 30, 2015·Proceedings of the National Academy of Sciences of the United States of America·Marie-Aude PlamontArnaud Gautier
Aug 23, 2017·Accounts of Chemical Research·Yasuyuki Tezuka
Dec 29, 2017·Angewandte Chemie·Giulia MorgeseEdmondo M Benetti
Apr 7, 2020·Nature Chemistry·Farihah M Haque, Scott M Grayson

❮ Previous
Next ❯

Methods Mentioned

BETA
nuclear magnetic resonance
size exclusion chromatography
transmission
atomic force microscopy
transmission electron microscopy
AFM
differential scanning calorimetry
NMR

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.