Thienopentathiepine: a sulfur containing fused heterocycle for conjugated systems and their electrochemical polymerization

Debnath, Sashi; Bedi, Anjan; Zade, Sanjio S.

doi:10.1039/c5py01133g

Cited by 24 publications

(9 citation statements)

References 35 publications

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“…Moreover, none of the polymers were soluble in NaOH (1.0 M), which suggested stability to basic hydrolysis at rt. Finally, the relatively inert nature of sulfide linkages within polymer backbones is well documented (Debnath et al, ; Nguyen et al, ; Wayne and Brady, ). However, organic sulfides are susceptible to oxidation to sulfoxides or sulfones, or mixtures thereof, when exposed to oxidants such as peroxides (Kaczorowska et al, ; Sato et al, ).…”

Section: Resultsmentioning

confidence: 99%

Renewable Poly(Thioether‐Ester)s from Fatty Acid Derivatives via Thiol‐Ene Photopolymerization

Moser

Doll

Peterson

2019

J Americ Oil Chem Soc

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Partially bio-based poly(thioether-ester)s were obtained in high conversion from thiol-ene photopolymerization of fatty dienes with dithiols utilizing mild, solventless reaction conditions. Fatty dienes were synthesized by esterification of 9-decenoic acid, a terminally unsaturated medium-chain fatty acid that can be obtained from ethenolysis of oleic acid, with ethylene glycol and 9-decen-1-ol to yield bio-based dienoic monomers amenable to subsequent thiol-ene polymerization. Polycondensation with 1,2-ethanedithiol (EDT) and 1,3-propanedithiol (PDT) gave a series of semicrystalline poly(thioether-ester) s with degrees of polymerization that ranged from 29 to 85, polydispersity indices between 2.81 and 4.38, and glass transitions from −36.8 to −25.7 C. The polymers were elastic at room temperature, with EDT-linked materials exhibiting greater elasticity than the corresponding PDTlinked polymers. All polymers were thermally stable below 320 C, with 10% mass loss (T 10 ) occurring above 338 C. Enthalpies of fusion increased with higher relative crystallinity and were greater than the corresponding enthalpies of crystallization. The polymers were soluble in nonpolar solvents such as chloroform and THF but resisted dissolution in more polar solvents with dielectric constants above 10. Furthermore, the polymers were susceptible to acidic hydrolysis but resisted basic hydrolysis at room temperature. J Am Oil Chem Soc (2019) 96: 825-837 826 J Am Oil Chem Soc J Am Oil Chem Soc (2019) 96: 825-837 a RCC = renewable carbon content = (renewable carbons) / (total carbons) in repeat unit (see Scheme 1). b Ð = polydispersity index = M w /M n . c DP = average degree of polymerization = M n /repeat unit MW. d Values in parentheses represent standard deviation from the reported mean (n = 3). 828 J Am Oil Chem Soc J Am Oil Chem Soc (2019) 96: 825-837

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Section: Resultsmentioning

confidence: 99%

Renewable Poly(Thioether‐Ester)s from Fatty Acid Derivatives via Thiol‐Ene Photopolymerization

Moser

Doll

Peterson

2019

J Americ Oil Chem Soc

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“…[150] The synthesis of new conjugated building blocks, diselenolodiselenole (C 4 Se 4 ) derivatives 279 was successfully afforded by using dialkyne 278 and Se powder (Scheme 90). [151][152] 7. Selenosulfonation…”

Section: Electrophilic Cyclization Of 13-diyne and 135-triynementioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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“…One of the most commonly used synthetic methods toward such polymers is a transition metal-catalyzed polycoupling reaction of prefunctionalized monomers with fused heterocyclic units. The involved coupling reactions included Suzuki, Kumada, Negishi, Stille, and Yamamoto cross-coupling reactions or direct arylation reactions, etc. − Condensation techniques such as the Heck and Sonogashira coupling reaction, Knoevenagel condensation, and Wittig–Horner–Emmons reaction have also been used to construct conjugated fused heterocyclic polymers with AIE features in which the newly formed unsaturated acyclic moiety serves as the linker to connect the fused (hetero)cyclic unit with the AIEgen-containing unit. − In some cases, oxidative coupling and the electropolymerization method were used to prepare fused heterocyclic polymers. , However, the aforementioned polymerizations generally require limited and costly fused aromatic substrates and a complicated synthesis of monomers with prefunctionalized fused heterocycles. Some of the polymerizations require elaborate reaction control, harsh reaction conditions, and difficult isolation procedures.…”

Section: Introductionmentioning

confidence: 99%

“…24−27 In some cases, oxidative coupling and the electropolymerization method were used to prepare fused heterocyclic polymers. 28,29 However, the aforementioned polymerizations generally require limited and costly fused aromatic substrates and a complicated synthesis of monomers with prefunctionalized fused heterocycles. Some of the polymerizations require elaborate reaction control, harsh reaction conditions, and difficult isolation procedures.…”

Section: Introductionmentioning

confidence: 99%

Fused Heterocyclic Polymers with Aggregation-Induced Emission: Synthesis and Applications

Fan

Wang

Han

et al. 2022

ACS Appl. Polym. Mater.

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Fused heterocyclic polymers with aggregation-induced emission (AIE) have attracted much attention due to their unique photoelectric properties, efficient aggregate-state fluorescence, high thermal stability, and superamplification effect as fluorescence sensors as well as multiple functionalities. Among various synthetic methodologies toward fused heterocyclic AIE polymers, polymerization based on triple bond-containing monomers such as alkynes and (iso)cyanides is a powerful synthesis tool that can in situ generate fused heterocyclic units in polymer backbones in high efficiency. In this Review, we summarize the recent progress in the synthesis of nitrogen-, oxygen-, and multiple heteroatom-containing fused cyclic polymers with AIE features based on polymerizations of triple bond-containing monomers. Furthermore, the high-tech applications of the corresponding fused heterocyclic AIE polymers in the visualization of morphological structures, fluorescence chemo-sensors, stimuli-responsive materials, and photodynamic therapy are illustrated. Finally, perspectives on the challenges and future development directions of this field are discussed.

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Thienopentathiepine: a sulfur containing fused heterocycle for conjugated systems and their electrochemical polymerization

Cited by 24 publications

References 35 publications

Renewable Poly(Thioether‐Ester)s from Fatty Acid Derivatives via Thiol‐Ene Photopolymerization

Renewable Poly(Thioether‐Ester)s from Fatty Acid Derivatives via Thiol‐Ene Photopolymerization

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Fused Heterocyclic Polymers with Aggregation-Induced Emission: Synthesis and Applications

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