Polythioamide and poly(1,3,4-thiadiazole) synthesis from dimethyl tetrathioterephthalate

Delfanne, Isabelle; Lévesque, Guy

doi:10.1021/ma00196a007

Cited by 22 publications

(17 citation statements)

References 6 publications

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“…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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Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

278

220

View full text Add to dashboard Cite

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“…Actually, PTA can be used as an absorbent material to selectively separate some heavy metals like mercury(II) and platinum(IV) from aqueous solutions. , More importantly, some PTAs exhibit high refractivity and luminescent behavior and thus have potential applications in advanced optoelectronics . Traditionally, PTA was synthesized through polycondensation reaction between dithioesters and diamines, which produced toxic and foul-smelling methanethiol byproduct. , Also, PTA could be obtained via postmodification of polyamide with the Lawesson reagent, but this methodology suffered the problems of hydrolytic degradation and incomplete conversion …”

Section: Introductionmentioning

confidence: 99%

“…8 Traditionally, PTA was synthesized through polycondensation reaction between dithioesters and diamines, which produced toxic and foul-smelling methanethiol byproduct. 9,10 Also, PTA could be obtained via postmodification of polyamide with the Lawesson reagent, but this methodology suffered the problems of hydrolytic degradation and incomplete conversion. 11 Elemental sulfur is an abundant and inexpensive material produced from natural gas and petroleum refinement.…”

Section: ■ Introductionmentioning

confidence: 99%

Polythioamides of High Refractive Index by Direct Polymerization of Aliphatic Primary Diamines in the Presence of Elemental Sulfur

Sun

Huang

et al. 2017

Macromolecules

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Sulfur-containing polymers have renewed widespread attention due to their fascinating properties like high refractive index and semiconducting character. However, examples of direct polymerization involving elemental sulfur are limited. Herein, a new strategy to prepare polythioamide (PTA) by direct polymerization of aliphatic primary diamines in the presence of sulfur is reported. The polymerization of p-xylylenediamine (1) and sulfur at 110 °C in N-methyl-2-pyrrolidinone afforded PTA1 of high M w and high yield when the feed ratio of [1]:[S] ranged from 1:2 to 1:3. 1H NMR and 13C NMR spectra confirmed that there are three kinds of structural units among the PTA1 chains. Moreover, different diamines including m-xylylenediamine (2), 1,6-hexanediamine (3), ethylenediamine (4), and 1,4-cyclohexanediamine (5) were copolymerized with 1 in the presence of sulfur to obtain PTA copolymers. With an increase in 5 content, the copolymer PTA1/5 with an alternating sequence in the range of 56%–94% was prepared. Solubility and thermal properties of homopolymers and copolymers were studied. Meanwhile, the copolymers PTA1/3 and PTA1/5 possessed a high refractive index as high as 1.7.

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“…Inclusion of phenylthiourea groups into polymer backbone has gained great importance for its excellent properties such as corrosion resistance, thermal stability, semi conductivity and binding to metal ions [9][10][11]. Polythioamides are well known in which the amide carbonyl oxygen is replaced with sulfur [12]. However, polyesters or polyamides bearing both azomethine and thiourea groups are different from polythioamides and is a relatively less explored area [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Metal Ion Adsorption Studies on Novel Aromatic Poly(Azomethine Amide)s Containing Thiourea Groups

Ravikumar¹,

Kalaivani²,

Vidhyadevi³

et al. 2014

OJPChem

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A series of novel ladder-type poly(azomethine amide)s (PAMs) were prepared from new azomethine containing carboxylic acid monomer (TCA) with simple aromatic diamines and aromatic diamines with thiourea groups (TDAs) by means of phosphorylation polycondensation reaction. Molecular weights of the polyamides were evaluated viscometrically, and the inherent viscosities were in the range of 0.31 -0.58 g/dl. These ladder-type polymers were not freely soluble in common organic solvents. Structure of monomers and polymers were confirmed using FT-IR, 1 H-NMR and 13 C-NMR spectroscopic analysis. Removal of Cu 2+ and Cd 2+ from aqueous solutions by adsorption onto the polyamides was investigated. The effect of pH, initial metal ion concentrations and contact time were studied in batch experiments. The polyamides were found to be highly effective adsorbents for the removal of Cu 2+ and Cd 2+ metal ions from aqueous solutions. In a mixture of metal ions, the selectivity order was found to be Pb(II) > Cu(II) > Cr(IV) > Cd(II).

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Polythioamide and poly(1,3,4-thiadiazole) synthesis from dimethyl tetrathioterephthalate

Cited by 22 publications

References 6 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Polythioamides of High Refractive Index by Direct Polymerization of Aliphatic Primary Diamines in the Presence of Elemental Sulfur

Synthesis, Characterization and Metal Ion Adsorption Studies on Novel Aromatic Poly(Azomethine Amide)s Containing Thiourea Groups

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