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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Preparation of Long-Chain-Alkyl Siloxanes Bridged by Carbon-Sulfur Bond via Thiol–Ene Reaction

Feng-Tao Zheng,Hai-Jun Zhang,Gaoxue Xu

Long-chain-alkyl siloxanes were commonly used as hydrophobic treatment agents in cotton fabrics. In this work, long-chain-alkyl siloxanes (S-Siloxanes) were prepared by thiol–ene reaction between polyvinylmethylsiloxanes (Si  CC) and 1-pentanethiol. Thermal behavior, glass transition temperature (Tg), crystallization property, and hydrophobic treatment performance were investigated and compared with those of commonly used long-chain-alkyl siloxanes (C-Siloxanes) prepared via hydrosilylation reaction with platinum as a catalyst. The results showed that S-Siloxanes were thermally stable up to 350°C and possessed similar Tg and crystallization performance as C-Siloxanes. Water contact angles of glasses and cotton fabrics treated by S-Siloxanes reached 87.67° and 96.33° respectively, which were significantly increased compared to untreated glasses and cotton fabrics of 36.27° and 0°. The results were similar for glasses and cotton fabrics treated by C-Siloxanes. This work provides a milder and greener method to synthesize long-chain-alkyl siloxanes.

研究领域: 材料科学 · 纺织化学
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ELECTROCHEMISTRY COMMUNICATIONS · 2011 · IF 4.287

Thiol-ene click chemistry for the fabrication of Ru(bpy)32+-based solid-state electrochemiluminescence sensor

Kai Zeng,Manli Guo,Yingjun Zhang,Meng Qing,Afang Liu,Zhou Nie,Yan Huang,Yuliang Pan,Shouzhuo Yao

A novel method based on click chemistry for the immobilization of Ru(bpy) 3 2+ derivative on electrode to fabricate a solid state electrochemiluminescence (ECL) sensor was reported. Pentenyl functionalized Ru(bpy′) 3 Cl 2 was synthesized and immobilized on a (3-mercaptopropyl) trimethoxysilane (MPTMS) pretreated indium tin oxide (ITO) substrate via thiol-ene click chemistry reaction between its alkenyl group and the sulfhydryl group of MPTMS. The immobilization method is simple, fast, and efficient. More importantly, the resulting Ru(bpy′) 3 2+ monolayer film exhibited excellent stability in organic solvent, which is superior to many previously reported methods. Using tri- n -propylamine (TPrA) as a model analyte, the ECL sensor gave a wide linear range over 5   ×   10 −   6 to 5   ×   10 −   3   M, with a satisfactory detection limit of 1   ×   10 −   6   M ( S / N   =   3).

研究领域: 分析化学 · 材料科学
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RSC Advances · 2016 ·Vol. 6 ·期 51 ·45193-45201 · IF 3.289

A new approach for the synthesis of sulfur-bridged polysiloxanes via thiol–ene “click” reaction and their post-functionalization to obtain luminescent materials

Yujing Zuo,Zhiming Gou,Jinfeng Cao,Xiaoxiao Li,Shengyu Feng

Polysiloxanes, also known as “silicones”, have received widespread attention as specialty and inorganic backbone polymers since their commercial introduction. However, traditional synthesis routes can only produce polymers with Si–O–Si bonds in the main chains; this limitation influences the rapid development of the silicone industry. As such, new methods for the synthesis of silicones must be developed. This study is the first to introduce the thiol–ene reaction as a modular, efficient, and highly orthogonal method for polymerization. Novel polysiloxanes bearing sulfur atoms in the main chain with adjustable molecular weight were synthesized by the thiol–ene “click” reaction of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane. 1,2-Ethanedithiol was subsequently functionalized using the same method. The structure of these polysiloxanes was characterized by 1H NMR, 13C NMR, and GPC analyses. The new structures of polysiloxanes bearing sulfur atoms in the main chain confer novel properties and applications. Furthermore, incorporating sulfur atoms could linearly increase the refractive index of polysiloxane. Finally, hybrid luminescent materials obtained from functionalized polysiloxanes and lanthanide ions exhibited narrow-width green or red emissions.

研究领域: 高分子化学 · 材料科学
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APPLIED SURFACE SCIENCE · 2017 · IF 3.387

Vapor-liquid interfacial reaction to fabricate superhydrophilic and underwater superoleophobic thiol-ene/silica hybrid decorated fabric for oil/water separation

Hongqiang Li,Tao Liang,Xuejun Lai,Xiaojing Su,Lin Zhang,Xingrong Zeng

With oil spill accidents and oil industrial wastewater increasing, oil/water separation has attracted much attention in recent years. Herein, we report the fabrication of superhydrophilic and underwater superoleophobic thiol-ene/silica hybrid decorated fabrics for oil/water separation via vapor-liquid interfacial reaction. It is based on sol-gel reaction of tetraethyl orthosilicate (TEOS) to generate silica and thiol-ene reaction between poly(ethylene glycol) dimethacrylate (PEGDMA) and trimethylolpropane tris(3-mercaptopropionate) (TTMP) to form crosslinked hydrophilic polymer on polyester fabric under the catalysis of butylamine/ammonia vapor. The chemical structure of the surfaces on thiol-ene/silica hybrid decorated fabric was confirmed by FTIR and XPS, and obvious micro-nano morphology and roughness were observed with SEM and AFM. The water contact angle of the fabric attained 0° in 0.36   s, and the underwater oil contact angle reached up to 160°. Importantly, the fabric exhibited high separation efficiency at 99.5%, fast water flux above 71600   Lm −2   h −1 and excellent recyclability in oil/water separation. Our findings open a new strategy to fabricate organic-inorganic hybrid superhydrophobic and underwater superoleophobic materials for oil/water separation.

研究领域: 材料科学 · 环境科学
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PROGRESS IN ORGANIC COATINGS · 2023 · IF 6.6

UV-curable silicone pressure-sensitive adhesive based on thiol-ene reaction

Yu Zhou,Zuyi Zhao,Zhaoxia Liu,Hongxiang Chen,Hongye Yan,Junjie Tan,Fan Li

In order to improve the curing efficiency and reduce energy consumption of silicone pressure-sensitive adhesive (SiPSA), a kind of UV-curable SiPSA based on thiol-ene reaction was prepared with methyl vinyl MQ resin as hard segment, methyl vinyl silicone rubber (110-2S) as soft segment and mercaptyl silicone oil as cross-linker. The UV-cured SiPSA exhibited excellent thermal stability and water resistance. Its physical features such as chemical composition, cross-linking extent and dispersion of MQ resin in silicone rubber were directly related to the vinyl content in MQ resin, the thiol/ene ratio and the resin/rubber ratio, which further affected mechanical properties and adhesive properties of SiPSA. With the vinyl content in MQ resin of 56 mmol/100 g, the thiol/ene molar ratio of 0.8 and the resin/rubber mass ratio of 1.4, the UV-cured SiPSA-B1.4–0.8 had better mechanical properties, moreover it had higher tensile shear strength of >2.0 MPa and showed interface failure on the surface of substrates, indicating that it had great potential applications as PSA.

CAS / MDL: 24650-42-8 107-06-2
研究领域: 材料科学 · 化学工程
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MATERIALS LETTERS · 2013 · IF 2.224

Preparation and characterization of novel UV-curing silicone rubber via thiol-ene reaction

Lei Xue,Yanyan Zhang,Yujing Zuo,Shen Diao,Jie Zhang,Shengyu Feng

A novel type of UV-curing silicone rubber was prepared via thiol-ene click reaction by using high-molecular-weight polydimethylsiloxane containing vinyl groups as the gum, polymercaptopropylmethylsiloxane as crosslinker, TS-530 SiO 2 as reinforcing filler and 2,2-dimethoxy-2-phenylacetophenone as photoinitiator. The obtained UV-curing silicone rubbers were transparent. The thermomechanical properties of resulting silicone rubbers were studied using dynamic mechanical analysis (DMA). Meanwhile, the mechanical property and thermal stability of the silicone rubber were also determined. Experimental results showed that the thiol-ene click reaction can be used as the alternative curing system to prepare the silicone rubber.

CAS / MDL: 24650-42-8 107-06-2
研究领域: 材料科学 · 化学工程
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CHEMICAL ENGINEERING COMMUNICATIONS · 2018 · IF 1.282

Synthesis of amphiphilic hyperbranched polyglycerol through “thiol-ene” chemistry and its application on the removal of industrial dyes

Qingwang Liu,Zhenzhong Fan,Baojun Bai,Jigang Wang,Lifeng Zhang,Ningning Zhan

An amphiphilic dodecyl-modified hyperbranched polyglycerol (DSHPG) with the core–shell structure and good solubility in n-hexane is prepared through “thiol-ene” reaction. The concentration of dye or DSHPG, temperature, contacting time, and molecular weight of DSHPG were taken into consideration to evaluate the transfer capability. It is shown that the extraction effect of this polymer on cationic dyes is better than that on anionic dyes. With malachite green as the experimental dye, the value of removal ratio can be as high as 98.6% in the period of 120 min. This “molecular nanocapsules” can extract dyes with high extraction rate and good efficiency, and the extraction process can be well described with the pseudo-first-order model. The reusability investigation confirms that the DSHPG can obtain appropriate applications in the extraction of dyes from wastewater due to the high adsorption efficiency and environmental-friendly economy.

研究领域: 材料科学 · 环境科学
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TALANTA · 2018 · IF 4.244

Hyperbranched anion exchangers prepared from thiol-ene modified polymeric substrates for suppressed ion chromatography

Kai Zhang,Chaoyan Lou,Yan Zhu,Mingyu Zhi,Xiuqiong Zeng

The covalent modification of polymeric particles has been a challenge due to their chemical inertness. Herein we describe a facile and neat method via thiol-ene reaction to immobilize cysteamine/cysteine onto allylmethacrylate-divinylbenzene (AMA-DVB) and ethylvinylbenzene-divinylbenzene (EVB-DVB). The introduced functionalities were verified by elementary analysis and scanning electron microscope coupled with energy dispersive spectroscopy . This modification enabled the further grafting of hyperbranched condensation polymers (HBCPs), which converted the particles into anion exchangers. The anion exchangers demonstrated good separation with carbonate/bicarbonate eluents and hydroxide eluents for suppressed anion exchange chromatography . In the case of a 3-layered anion exchanger, simultaneous separation of nine model anions was achieved by isocratic elution in 17 min with efficiencies up to 16,100 plates m −1 . High stability and dependable durability was exhibited in long-term tests.

研究领域: 分析化学 · 材料科学
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PROGRESS IN ORGANIC COATINGS · 2016 · IF 2.632

A facile fabrication of robust thiol-ene/hierarchically mesoporous silica nanoparticles hybrid superhydrophilic coating films under UV radiation

Tao Liang,Hongqiang Li,Xiaojing Su,Xuejun Lai,Huiqin Wu,Chuang Wang,Yang Wang,Mengdi Zhuang,Xingrong Zeng

We report a facile approach to designing the robust organic-inorganic hybrid superhydrophilic coating films under UV radiation. It is based on the utilization of ene-terminated hydrophilic oligomer (ETHO) and hierarchically mesoporous silica nanoparticles (HMSNs). ETHO was firstly synthesized with dl -dithiothreitol and excess of poly(ethylene glycol) dimethacrylate at room temperature via thiol-ene reaction, and then by spraying the methanol solution containing ETHO, HMSNs , trimethylolpropane triacrylate as crosslinking agent, and Darocur 1173 as photoinitiator on substrate, the thiol-ene/HMSNs hybrid superhydrophilic coating films were fabricated under the exposure of UV light. The structure of ETHO was confirmed by FT-IR, 1 H NMR and 13 C NMR, its molecular weight was 7600 measured by GPC. The wetting behavior of the coating films was found to be largely determined by the mass ratio of HMSNs to ETHO. With the mass ratio at 0.75, the hybrid coating films could achieve superhydrophilic state within 0.24   s, and SEM revealed the existence of double micro-nano structure on the surface, which was significant for the improvement of superhydrophilicity. Importantly, the superhydrophilicity of the coating film could be steadily maintained under the conditions of acid solution, boiling water and abrasion. Additionally, the coating films also exhibited excellent adhesion, flexibility and impact strength.

研究领域: 材料科学 · 化学工程
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