Design and property of thermoresponsive core-shell fluorescent nanoparticles via RAFT polymerization and suzuki coupling reaction

Xing, Zeyong; Zhang, Jian; Li, Xiaohong; Zhang, Wei; Wang, Laibing; Zhou, Nianchen; Zhu, Xiulin

doi:10.1002/pola.26822

Cited by 7 publications

(3 citation statements)

References 40 publications

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“…Soft materials are particularly interesting candidates for in situ imaging due to the fact that in solution their morphology can be manipulated by a broad range of stimuli including metals, pH, temperature, light, redox chemistry, ultrasound, DNA hybridization, and enzymes . Furthermore, organic liposomes and synthetic polymer vesicles have been imaged via in situ TEM but only as stationary, static objects, ,, which have sometimes appeared crenated as if dehydrated .…”

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confidence: 99%

Dynamics of Soft Nanomaterials Captured by Transmission Electron Microscopy in Liquid Water

et al. 2014

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In this paper we present in situ transmission electron microscopy (TEM) of synthetic polymeric nanoparticles with emphasis on capturing motion in a solvated, aqueous state. The nanoparticles studied were obtained from the direct polymerization of a Pt(II)-containing monomer. The resulting structures provided sufficient contrast for facile imaging in situ. We contend that this technique will quickly become essential in the characterization of analogous systems, especially where dynamics are of interest in the solvated state. We describe the preparation of the synthetic micellar nanoparticles together with their characterization and motion in liquid water with comparison to conventional electron microscopy analyses.

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confidence: 99%

Dynamics of Soft Nanomaterials Captured by Transmission Electron Microscopy in Liquid Water

et al. 2014

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“…To date, PPM of RDRP derived polymers using Pd-SMC is underutilized, in spite of the minimal limitations impeding its implementation outside the interference of thiol or thioester blocking groups. , Accounts of Pd-catalyzed cross-coupling for PPM have been reported; however, focus has resided primarily on Sonogashira cross-coupling of functional alkynes onto bromine functional homopolymers , and iodine functional hyperbranched polymers . In the limited instances of Pd-SMC and RAFT, Pd-SMC has been almost exclusively explored as a tool for creating core–shell nanoparticles, − as a cross-linking method for homopolymers and block copolymers, and for synthesizing cyclic bottlebrushes via a “grafting-to” approach . Mori and co-workers demonstrated RAFT polymerization of bromophenyl vinyl sulfide and its subsequent Pd-SMC; however, a limited scope of boronic acids were explored consisting of two fully hydrocarbon boronic acids .…”

Section: Introductionmentioning

confidence: 99%

From Click Chemistry to Cross-Coupling: Designer Polymers from One Efficient Reaction

2017

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Palladium-catalyzed Suzuki−Miyaura cross-coupling was demonstrated to be a versatile reaction platform to install functional groups onto well-defined polymers derived from reversible addition−fragmentation chain-transfer (RAFT) polymerization. Cross-coupled products were achieved utilizing a range of functional boronic acids including, but not limited to, furan, alkyloxyphenyl, methacrylamide, trifluorophenyl, anthracene, and dimethylaminophenyl. High to quantitative degrees of functionalization were obtained by employing convenient reaction conditions at low to moderate temperatures (23−60 °C), within short reaction times (2−16 h), while using air-stable reagents at 1.5−3.0 equiv. of boronic acid. Specifically, a custom monomer, N-[2-(4-bromophenyl)ethyl]acrylamide (BPEA), was synthesized bearing a reactive handle for subsequent cross-coupling, and its chemical structure was verified using nuclear magnetic resonance. RAFT polymerization of BPEA revealed attributes of a successful reversible-deactivation radical polymerization (RDRP) yielding polymers with predetermined molecular weights and narrow dispersity values (Đ < 1.3). The retention of living chain ends was evidenced by efficient chain extension of poly(BPEA) with N-isopropylacrylamide producing a low dispersity diblock copolymer. Optimal functionalizations were found to be achieved through removal of the RAFT chain transfer agent and, in specific instances, by functionalizing statistical copolymers. The utility of this functionalization strategy, when combined with RDRP, has the ability to provide potentially thousands of structurally diverse functionalized polymers, elucidate quantitative structure−property relationships, and create new avenues to advanced polymeric architectures.

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“…Mori et al [34] reported the first successful synthesis of a carbazole-based side chain polymer (poly(N-vinylcarbazole)) using the RAFT technique. Most recently, Zhu et al [35] prepared an amphiphilic copolymer poly(DBCzMA-b-NIPAM) through a two-step RAFT reaction using poly(6-(2,7-dibromo-9H-carbazole-9-yl) hexyl methacrylate) (poly(DBCzMA)) as the macro-chain transfer agent (macro-CTA) and poly(N-isopropylacrylamide) (PNIPAM) as the second monomer. Consequently, the modification of 2,7-dibromide groups in poly(DBCzMA-b-NIPAM) using the Suzuki coupling method (which reacted with a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-based carbazole monomer) obtained a poly(2,7-carbazole)-containing crosslinked polymer with the appearance of uniform core-shell fluorescent nanoparticles dissolved in water.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Chemosensory Properties, and Self-Assembly of Terpyridine-Containing Conjugated Polycarbazole through RAFT Polymerization and Heck Coupling Reaction

Yang

Chien

et al. 2017

Polymers

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Abstract:We report the responsive fluorescence chemosensory phenomena of a carbazolefunctionalized crosslinked polymer (PCaT) with pendent terpyridine (tpy) groups as receptors of metal ions. The polymer was synthesized using Heck polymerization between 3,6-dibromide groups in a carbazole-based polymer (PC2Br) and divinyl tpy monomer. The effects of the polymeric structure on the optical and chemosensory properties of the PCaT were compared with those of a carbazole-tpy alternating conjugated polymer (PCT). Photoluminescence titrations demonstrated that the PCaT and PCT had the high sensing ability toward Fe 3+ ions, with Stern-Volmer constants of 8.10 × 10 4 and 6.68 × 10 4 M −1 , respectively. The limit of detection (LOD) toward Fe 3+ of the PCaT and PCT was estimated to be 1.31 × 10 −6 and 1.81 × 10 −6 M, respectively, and the superior LOD of the PCaT was ascribed to its lowly crosslinked structure. The fluorescence of the solutions of these polymers that were quenched by Fe 3+ ions recovered when trace CN − anions were added because of the high stability constant of the CN − -Fe 3+ complex. Micellar aggregates with a mean diameter of approximately 239.5 nm were formed by dissolving the PCaT in tetrahydrofuran (THF) solution. Our results suggest that the PCaT is a promising material for chemosensory applications.

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Design and property of thermoresponsive core-shell fluorescent nanoparticles via RAFT polymerization and suzuki coupling reaction

Cited by 7 publications

References 40 publications

Dynamics of Soft Nanomaterials Captured by Transmission Electron Microscopy in Liquid Water

Dynamics of Soft Nanomaterials Captured by Transmission Electron Microscopy in Liquid Water

From Click Chemistry to Cross-Coupling: Designer Polymers from One Efficient Reaction

Synthesis, Chemosensory Properties, and Self-Assembly of Terpyridine-Containing Conjugated Polycarbazole through RAFT Polymerization and Heck Coupling Reaction

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