Synthesis of hydroxyl-terminated polybutadiene bearing pendant carboxyl groups by combination of anionic polymerization and blue light photocatalytic thiol-ene reaction and its pH-triggered self-assemble behavior

Zhang, Wanbin; Zhang, Guanghua; Du, Lun; Zhang, Ce; Li, Lü; Zhu, Junfeng; Pei, Jing; Wu, Jiang

doi:10.1016/j.reactfunctpolym.2018.04.003

Cited by 18 publications

(13 citation statements)

References 47 publications

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“…Moreover, the bands identified at 726, 967, and 911 cm −1 are typical for cis-1,4-, trans-1,4-, and 1,2-polybutadiene, respectively, while the band at 697 cm −1 is characteristic to the benzene ring of polystyrene. Based on a literature review [15], it can be confirmed that the SBS block copolymer exhibiting terminal hydroxyl groups has been successfully obtained.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, the HO–SBS–OH block copolymer was characterized by 13 C NMR to assess the extent of cis-1,4 content (Figure 4). The spectrum displays a peak at 27.4 ppm, which is characteristic of the CH 2 of a cis-1,4-butadiene unit [15] and another at 32.7 ppm, typical for trans-1,4 carbons. Based on the integration of the peaks, cis-1,4 content was calculated at 90.4% for the HO–SBS–OH block copolymer synthesized via the novel [η 3 -Ni(CH 2 CHCHCH 2 OOCH 3 )][BPh F 4 ] catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…While the synthesis of polystyrene-polybutadiene block copolymers with high cis-1,4 content via transition metal catalysts is highly studied [9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28], to the best of our knowledge, no report on the synthesis of hydroxyl terminated polystyrene-polybutadiene block copolymers in the presence of these catalysts is known. This is due to the fact that the surface of these catalysts requires suitable chemical modification to improve their activity in the presence of alkyl aluminum (e.g., methylaluminoxane and triethylaluminum) as co-catalysts.…”

Section: Introductionmentioning

confidence: 99%

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A New Strategy for the Synthesis of Hydroxyl Terminated Polystyrene-b-Polybutadiene-b-Polystyrene Triblock Copolymer with High Cis-1, 4 Content

Min

Fan

2019

Polymers

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This work reports the preparation of a hydroxyl terminated polystyrene-b-polybutadiene-b-polystyrene triblock copolymer (SBS) with high cis-1, 4 content via a novel nickel catalyst, [η3-Ni(CH2CHCHCH2OOCH3)][BPhF4]. FT-IR, 1H-NMR, and 13C NMR indicated that the polybutadiene segment of the copolymer contains greater than 90% cis-1, 4 structure, indicating achievement of the objective. Toward the functionalization goal, a hydroxyl group was successfully introduced at the end of the triblock copolymer (HO–SBS–OH). The results of gel permeation chromatography (GPC) revealed that the polymer is indeed a triblock copolymer, with no traces of homopolymer. Differential scanning calorimetry (DSC) showed that HO–SBS–OH synthesized using the novel catalyst had a lower glass transition temperature (Tg) than HO–SBS–OH synthesized with an alkyl lithium catalyst. Therefore, the polymer synthesized via the novel catalyst contains high cis-1,4 content and displays excellent low-temperature mechanical properties.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A New Strategy for the Synthesis of Hydroxyl Terminated Polystyrene-b-Polybutadiene-b-Polystyrene Triblock Copolymer with High Cis-1, 4 Content

Min

Fan

2019

Polymers

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“…Recently, it was reported that thiol-ene reaction could be initiated at room temperature by visible light using novel visible-light-absorbing transition metal photocatalysts, becoming widely available for the synthesis of small molecular compounds [28,29,30,31]. As for polymers, Boyer and Zhang reported the thiol-ene modification of polybutadiene using visible light, showing that all double bonds were converted in a short time [32,33].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Side-Chain Functionalized Polytetrahydrofuran Derivatives via the Blue-Light Photocatalytic Thiol-Ene Reaction

et al. 2019

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A series of side-chain functionalized polytetrahydrofuran (PTHF) derivatives were synthesized via the blue-light photocatalytic thiol-ene “click” reaction. Firstly, unsaturated polytetrahydrofuran (UPTHF) as a new unsaturated polyether was synthesized via condensation polymerization of cis-2-butene-1,4-diol and trans-1,4-dibromo-2-butene using potassium hydroxide (KOH) as a catalyst. Then, double bonds in the backbone of UPTHF were modified into different pendant functionality side groups by blue-light photocatalytic thiol-ene “click” reaction using Ru(bpy)3Cl2 as a photoredox catalyst, obtaining different side-chain functionalized PTHF derivatives. The structure and the morphology of the side-chain functionalized PTHF derivatives was characterized via Fourier-transform infrared spectra (FTIR), nuclear magnetic resonance (NMR), size exclusion chromatography/multi-angle laser light scattering (SEC/MALLS), and differential scanning calorimeter (DSC). The results showed that the blue-light photocatalytic thiol-ene reaction exhibited high efficiency, and all the unsaturated bonds were modified. Different branch units bestowed different performance of PTHF derivatives; we systematically investigated the thermal properties, pH-triggered and temperature-triggered, self-assembly behaviors of different PTHF derivatives.

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“…For example, a series of pH-tunable thermoresponsive PEO-based functional polymers were prepared by thiol-ene “click” reaction [16]. In addition, Zhang and coworkers reported the thiol-ene modification of polybutadiene to obtain pH-responsive polyethylene derivatives using visible light, showing that all double bonds were converted in a short time [34]. Regretful, no matter small molecule modification or postpolymerization modification, the synthesis of temperature and pH dual-responsive polymers mainly confined to the linear or brush polymer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel pH-Tunable Thermoresponsive Hydroxyl-Terminated Hyperbranched Polyether

et al. 2019

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In this study, a new pH-tunable thermoresponsive hydroxyl-terminated hyperbranched polyether (HTHP 2) was successfully prepared via a one-pot cationic polymerization technique and postmodification. In the first step, hydroxyl-terminated hyperbranched polyether containing double bonds (HTHP 1) were synthesized. Then, through thiol-ene “click” reaction, pH-responsive carboxyl groups were introduced to the target polymer of HTHP 2. The products were characterized via Fourier-transform infrared spectra (FTIR), nuclear magnetic resonance (NMR), and size-exclusion chromatography-multiangle laser light scattering (SEC-MALLS). Moreover, dynamic light scattering (DLS) and UV–Vis spectroscopy was employed to study the pH- and thermoresponsiveness in detail. Results showed that HTHP 2 possessed typical pH-controllable thermoresponsive behavior. By regulating the solution pH value range 3.0–5.4, LCST of HTHP 2 could be changed from 12.8 to 68.0 °C. Meanwhile, the cell viabilities of A549 cells were more than 80% for in vitro cytotoxicity tests of HTHP 2, suggested that HTHP 2 polymers are of good biocompatibility for up to 24 h.

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Synthesis of hydroxyl-terminated polybutadiene bearing pendant carboxyl groups by combination of anionic polymerization and blue light photocatalytic thiol-ene reaction and its pH-triggered self-assemble behavior

Cited by 18 publications

References 47 publications

A New Strategy for the Synthesis of Hydroxyl Terminated Polystyrene-b-Polybutadiene-b-Polystyrene Triblock Copolymer with High Cis-1, 4 Content

A New Strategy for the Synthesis of Hydroxyl Terminated Polystyrene-b-Polybutadiene-b-Polystyrene Triblock Copolymer with High Cis-1, 4 Content

Synthesis and Properties of Side-Chain Functionalized Polytetrahydrofuran Derivatives via the Blue-Light Photocatalytic Thiol-Ene Reaction

Synthesis of Novel pH-Tunable Thermoresponsive Hydroxyl-Terminated Hyperbranched Polyether

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