Facile one-pot/one-step technique for preparation of side-chain functionalized polymers: Combination of SET-RAFT polymerization of azide vinyl monomer and click chemistry

2011 ◽  
Vol 50 (6) ◽  
pp. 1120-1126 ◽  
Author(s):  
Qiong Shen ◽  
Jian Zhang ◽  
Shuangshuang Zhang ◽  
Yigang Hao ◽  
Wei Zhang ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Raft Polymerization ◽  
Vinyl Monomer ◽  
Functionalized Polymers ◽  
Side Chain ◽  
One Pot ◽  
One Step

scholarly journals Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides

2016 ◽  
Vol 12 ◽  
pp. 1772-1777 ◽  
Author(s):  
Lena Huck ◽  
Juan F González ◽  
Elena de la Cuesta ◽  
J Carlos Menéndez
Keyword(s):  
Single Step ◽  
Side Chain ◽  
One Pot ◽  
Aziridine Ring ◽  
Component Process ◽  
Mild Conditions ◽  
One Step

A sequential three-component process is described, starting from 3-arylmethylene-2,5-piperazinediones and involving a one-pot sequence of reactions achieving regioselective opening of the 2,5-diketopiperazine ring and diastereoselective generation of an aziridine ring. This method allows the preparation of N-unprotected, trisubstituted aziridines bearing a peptide side chain under mild conditions. Their transformation into β-trifluoroacetamido-α-ketoamide and α,β-diketoamide frameworks was also achieved in a single step.

One-Pot RAFT/“Click” Chemistry via Isocyanates: Efficient Synthesis of α-End-Functionalized Polymers

2012 ◽  
Vol 134 (30) ◽  
pp. 12596-12603 ◽  
Author(s):  
Guillaume Gody ◽  
Christian Rossner ◽  
John Moraes ◽  
Philipp Vana ◽  
Thomas Maschmeyer ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Functionalized Polymers ◽  
Efficient Synthesis ◽  
One Pot

Producing bimodal molecular weight distribution polymers through facile one-pot/one-step RAFT polymerization

2012 ◽  
Vol 50 (19) ◽  
pp. 4103-4109 ◽  
Author(s):  
Hongjuan Jiang ◽  
Lifen Zhang ◽  
Jian Qin ◽  
Wei Zhang ◽  
Zhenping Cheng ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Molecular Weight Distribution ◽  
Weight Distribution ◽  
Raft Polymerization ◽  
One Pot ◽  
One Step

Synthesis and characterization of innovative well-defined difluorophosphonylated-(co)polymers by RAFT polymerization

2015 ◽  
Vol 6 (25) ◽  
pp. 4597-4604 ◽  
Author(s):  
Hien The Ho ◽  
Justine Coupris ◽  
Sagrario Pascual ◽  
Laurent Fontaine ◽  
Thierry Lequeux ◽  
...  
Keyword(s):  
Raft Polymerization ◽  
Functionalized Polymers ◽  
Side Chain ◽  
Synthesis And Characterization

Well-defined polymers incorporating difluorophosphonylated moieties in the side-chain and at the chain-end were synthesized by RAFT polymerization. The dealkylation of phosphonate ester groups was achieved in order to target difluorophosphonic acid functionalized polymers.

Functionalized Chitosan for Pharmaceutical Applications

2017 ◽  
Vol 14 (6) ◽  
pp. 785-797 ◽  
Author(s):  
Catalina Natalia Cheaburu-Yilmaz ◽  
Sinem Yaprak Karavana ◽  
Onur Yilmaz
Keyword(s):  
Block Copolymers ◽  
Chemical Modification ◽  
Click Chemistry ◽  
Raft Polymerization ◽  
Pharmaceutical Formulations ◽  
Side Chain ◽  
Structural Variations ◽  
Pharmaceutical Applications ◽  
Chemoselective Synthesis ◽  
Fast Procedure

Background: Chitosan structure versatility toward a change in an external stimulus represents a “must have” for the pharmaceutical applications, especially for the pharmaceutical formulations. Chemical modification can open new ways to obtain materials with tailored properties. Despite the great interest for conventional graft modifications, controlled/living free radical polymerizations (i.e. RAFT, ATRP, etc.) and advanced chemistry techniques (i.e. click chemistry) seem more attractive nowadays and involve facile and fast procedure, high regioselectivity, quantitative yield, mild reaction conditions without generation of by-products. Objective: The present review provides a detailed state of art of the chemical modification of chitosan i.e. tailored side-chain functionalization using RAFT polymerization and click chemistry for specific applications within pharmaceutical formulations taking into account the applicative aspect regarding the need of pharmaceuticals. Conclusion: The review showed the routes of current approaches for side chain modification of chitosan including graft, block copolymers or other structural variations. The esterification of RAFT agents on chitosan by using carbonyl activating reagents enables producing chitosan graft and block copolymers with controlled architectures while the development of protection/ deprotection chemistry of chitosan made possible the regioselective modification of chitosan or other polysaccharides. Although these developments increased the potential of chitosan, still the chemical functionality and architectural diversity of the derivatives are limited. Application of modern techniques e.g. RAFT polymerization, “click” chemistry has opened new “doors” for the science of controlled and chemoselective synthesis of well- tailored derivatives with unique and superior properties.

Facile one-step solid-phase synthesis of multitopic organic–DNA hybrids via “click” chemistry

2014 ◽  
Vol 5 (3) ◽  
pp. 1091-1096 ◽  
Author(s):  
Ryan V. Thaner ◽  
Ibrahim Eryazici ◽  
Omar K. Farha ◽  
Chad A. Mirkin ◽  
SonBinh T. Nguyen
Keyword(s):  
Click Chemistry ◽  
Small Molecule ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
One Pot ◽  
Phase Synthesis ◽  
One Step

Small molecule–DNA hybrids can be synthesized in a one-pot fashion and in good yields by coupling multiazide cores to alkyne-modified DNAs on a solid support using click chemistry.

Synergistic Interaction Between ATRP and RAFT: Taking the Best of Each World

2009 ◽  
Vol 62 (11) ◽  
pp. 1384 ◽  
Author(s):  
Yungwan Kwak ◽  
Renaud Nicolaÿ ◽  
Krzysztof Matyjaszewski
Keyword(s):  
Chain Transfer ◽  
Raft Polymerization ◽  
Atom Transfer ◽  
Step Method ◽  
One Pot ◽  
Reversible Addition ◽  
Raft Agent ◽  
Recent Developments ◽  
One Step ◽  
Leaving Groups

This review covers recent developments on the combination of atom transfer radical polymerization (ATRP) and reversible addition–fragmentation chain transfer (RAFT) polymerization to produce well controlled (co)polymers. This review discusses the relative reactivity of the R group in ATRP and RAFT, provides a comparison of dithiocarbamate (DC), trithiocarbonate (TTC), dithioester (DTE), and xanthate versus bromine or chlorine, and an optimization of catalyst/ligand selection. The level of control in iniferter polymerization with DC was greatly improved by the addition of a copper complex. New TTC inifers with bromopropionate and bromoisobutyrate groups have been prepared to conduct, concurrently or sequentially, ATRP from Br-end groups, ATRP from the TTC moiety, and RAFT polymerization from the TTC moiety, depending on the combination of monomer and catalyst employed in the reaction. The use of concurrent ATRP/RAFT (or copper-catalyzed RAFT polymerization or ATRP with dithioester leaving groups), resulted in improved control over the synthesis of homo- and block (co)polymers and allowed preparation of well-defined high-molecular-weight polymers exceeding 1 million. Block copolymers that could not be prepared previously have been synthesized by sequential ATRP and RAFT polymerization using a bromoxanthate inifer. A simple, versatile, and one-step method involving atom-transfer radical addition–fragmentation (ATRAF) for the preparation of various chain transfer agents (including DC, DTE, and xanthate) in high purity is discussed and a one-pot, two-step polymerization starting with a RAFT agent synthesized by ATRAF, followed by polymerization, is demonstrated.

A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

2020 ◽  
Vol 24 (4) ◽  
pp. 465-471 ◽  
Author(s):  
Zita Rádai ◽  
Réka Szabó ◽  
Áron Szigetvári ◽  
Nóra Zsuzsa Kiss ◽  
Zoltán Mucsi ◽  
...  
Keyword(s):  
Quantum Chemical ◽  
Room Temperature ◽  
Phase Transfer ◽  
One Pot ◽  
Substrate Dependence ◽  
Triethylbenzylammonium Chloride ◽  
One Step ◽  
The Pudovik Reaction ◽  
The One ◽  
Solid Liquid

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

scholarly journals Aqueous one-pot synthesis of well-defined zwitterionic diblock copolymers by RAFT polymerization: an efficient and environmentally-friendly route to a useful dispersant for aqueous pigments

2021 ◽  
Vol 23 (3) ◽  
pp. 1248-1258
Author(s):  
Shannon M. North ◽  
Steven P. Armes
Keyword(s):  
Iron Oxide ◽  
Diblock Copolymers ◽  
Raft Polymerization ◽  
Environmentally Friendly ◽  
Iron Oxide Particles ◽  
One Pot ◽  
One Pot Synthesis ◽  
Highly Effective ◽  
Oxide Particles

An atom-efficient, wholly aqueous one-pot synthesis of zwitterionic diblock copolymers has been devised. Such copolymers can serve as highly effective aqueous dispersants for nano-sized transparent yellow iron oxide particles.

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