Polythioamide synthesis through chemical modification of polyamides

Deletre, Mylene; Lévesque, Guy

doi:10.1021/ma00224a019

Cited by 18 publications

(19 citation statements)

References 4 publications

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“…The obtained polythioamides exhibit good solubility in organic solvents rather than the analogous polyamide as in previous reports on polythioamides 1–3. PTA‐1 has good solubility in chloroform, TCE, DMAc, N ‐methyl‐2‐pyrrolidinone (NMP), and pyridine at room temperature, and is soluble in DMF and tetrahydrofuran on heating, whereas the analogous polyamide PA‐1 is soluble in chloroform and TCE but insoluble in other common organic solvents.…”

Section: Resultssupporting

confidence: 56%

“…In contrast to the extensive study of polyamides in the field of polymer chemistry, the preparation and characterization of polythioamides, in which the carbonyl oxygen has been replaced by sulfur, have been limited 1–3. Several condensation‐type polythioamides were previously prepared from bis(thioester)s1 or bis(dithioester)s2 with diamines.…”

Section: Introductionmentioning

confidence: 99%

“…These factors might restrict the study and usability of the polythioamides. Thus, the thionation of finely divided polyamides by Lawesson's reagent, 2,4‐bis(4‐methoxyphenyl)‐1,3‐dithia‐2,4‐diphosphetane‐2,4‐disulfide, has also been reported as an alternative method 3, 4…”

Section: Introductionmentioning

confidence: 99%

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Planning for the future—Development of action criteria that balance regulatory risks versus market and production requirements at an opthalmic lens coating facility

Hangal¹,

Hober²,

Sweeney

2004

Environ. Prog.

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Section: Resultssupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

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Planning for the future—Development of action criteria that balance regulatory risks versus market and production requirements at an opthalmic lens coating facility

Hangal¹,

Hober²,

Sweeney

2004

Environ. Prog.

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“…The kinetics of the thioamidation have been investigated for reactions between aliphatic mono‐ (and bisdithioesters) and aliphatic amines. The results of this investigation revealed that the thioamidation reaction is very fast, highly specific and irreversible . However, the preparation of the dithioesters or didithioesters and the subsequent disposal of the harmful methanethiol after polymerization is critical, hence this is restricting the study and usability of the polythioamides prepared by the abovementioned method.…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

278

220

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The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201800650. ChemistryBefore moving to the recent advances within the last 5 years in the diverse applications of sulfur chemistry in polymer and Sulfur-Containing PolymersSulfur and its functional groups are major players in an area of exciting research taking place in modern polymer and materials science, both in academia and industry. In fact, manifold sulfur-based reactions that are both exceptionally versatile as well as tremendously useful have been implemented, and further utilized for the design and preparation of polymeric materials that lead to a plethora of applications ranging from medicine to optics and nanotechnology to separation science. Hence, within this review, an overview of strategies and developments used over the last 5 years to reinforce the importance of the sulfur functional group in modern polymer and materials science is presented. In particular, many important references in the primary literature of sulfur chemistry are referred to, including thiol-ene, thiol-yne, thiol-Michael addition, disulfide cross-linking, and thiol-disulfide exchange, among others, by explaining and illustrating the important principles. Last but not least, the grand aim to underpin the importance of sulfur in modern polymer and materials science is achieved by presenting selected examples in diverse fields and postulating the respective potential for real-world applications. he is now a full professor at KIT.sulfur atoms, and tetraphenylethene-bearing di(alkyl bromide) (Scheme 3). The yield of the polymerization was dependent on the di(alkyl bromide) monomer; the longer spacer between the aromatic moiety and the reactive bromide end groups Scheme 1. The discussion henceforth focuses on the synthesis of polymers possessing the depicted sulfur functional groups. Scheme 2.Representative examples of polythioethers prepared via A) the nucleophilic substitution reaction between an electrophilic dihalide with nucleophilic derivatives of dithiols under alkaline conditions; B) the thiol-ene/yne addition reaction between AA and BB type monomers (i.e., dithiols and dienes/diynes); and C) radical or ionic ring-opening of sulfurcontaining strained rings.Scheme 3. The thiol-bromo polymerization of conformationally fixed monomers to provide multifunctional polymers. [19] Macromol. Rapid Commun. 2019, 40, 1800650 Scheme 4. The regioselective selective nucleophilic aromatic substitution between thiol and fluorinated aromatic compounds, the para-fluorothiol reaction (PFTR).Scheme 5. Synthesis of a linear polymer via PFTR-reaction. [21]

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“…It would be expected from previous studies that the primary aminecontaining monomer would react with the CTA in attempted RAFT synthesis, because thiocarbonylthio agents -in this case a macro trithiocarbonate -are known to react with a primary amine via aminolysis, yielding thioamides and thiols. [43,44] However, by carefully controlling the polymerization conditions and keeping the aqueous polymerization solution between a pH of 4.0 and 5.0, hydrolysis and/or aminolysis of the CTA can be largely eliminated. [26,45] As reported in our previous publication, [41] diblock copolymer precursors and several triblock copolymers with different block lengths have been synthesized.…”

Section: Resultsmentioning

confidence: 99%

Facile 'One-Pot' Preparation of Reversible, Disulfide-Containing Shell Cross-Linked Micelles from a RAFT-Synthesized, pH-Responsive Triblock Copolymer in Water at Room Temperature

Smith

McCormick

2009

Aust. J. Chem.

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A pH-responsive triblock copolymer, α-methoxy poly(ethylene oxide)-b-poly(N -(3-aminopropyl) methacrylamide)β-poly(2-(diisopropylamino)ethyl methacrylate) (mPEO-PAPMA-PDPAEMA), was synthesized via aqueous RAFT polymerization. This triblock copolymer dissolves in aqueous solution at low pH (<5.0) due to protonation of primary amine residues on the PAPMA block and tertiary amine residues on the PDPAEMA block. Above pH 6.0, the copolymer unimers self-assemble into micelles consisting of PDPAEMA cores, PAPMA shells, and mPEO coronas. Dynamic light scattering studies indicated a hydrodynamic diameter of 92 nm at pH 9.0. A bifunctional, reversible cross-linker, dimethyl 3,3 -dithiobispropionimidate (DTBP), was used to cross-link the micelles. The 'one-pot' formation of shell cross-linked (SCL) micelles was accomplished at room temperature in water by mixing the triblock copolymers and DTBP at pH 3.0, and slowly increasing the solution pH to 9.0 leading to the simultaneous formation of micelles and cross-linking. These SCL micelles are readily cleaved by the addition of the reducing agent, dithiothreitol, and can be re-cross-linked simply by exposure to air. Such SCL micelles have potential as nanocarriers for controlled release of therapeutic and diagnostic agents because the in situ cleavage of the disulfide linkages would not only allow release of bioactive agents, but also permit renal clearance of the resulting unimeric components.

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Polythioamide synthesis through chemical modification of polyamides

Cited by 18 publications

References 4 publications

Planning for the future—Development of action criteria that balance regulatory risks versus market and production requirements at an opthalmic lens coating facility

Planning for the future—Development of action criteria that balance regulatory risks versus market and production requirements at an opthalmic lens coating facility

Sulfur Chemistry in Polymer and Materials Science

Facile 'One-Pot' Preparation of Reversible, Disulfide-Containing Shell Cross-Linked Micelles from a RAFT-Synthesized, pH-Responsive Triblock Copolymer in Water at Room Temperature

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