The introduction of the Barbier reaction into polymer chemistry

Sun, Xiaoli; Liu, Dong-Ming; Tian, Di; Zhang, Xiaoyun; Wu, Wei; Wan, Wen‐Ming

doi:10.1038/s41467-017-01472-w

Cited by 61 publications

(38 citation statements)

References 32 publications

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“…To demonstrate the applications of pyrene-containing NBN-doped PAHs, the artificial light-harvesting film was prepared with Py-NBN-Ph as donor and nile red (NiR) as acceptor, because the absorption of the NiR acceptor overlaps with the emission of the Py-NBN-Ph donor [ 55 , 56 , 57 , 58 ]. The artificial light-harvesting films were prepared with different Py-NBN-Ph/NiR ratios.…”

Section: Resultsmentioning

confidence: 99%

Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons

Xiao

Sun

et al. 2022

Molecules

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Pyrene molecules containing NBN-doped polycyclic aromatic hydrocarbons (PAHs) have been synthesized by a simple and efficient intermolecular dehydration reaction between 1-pyrenylboronic acid and aromatic diamine. Pyrene-B (o-phenylenediamine) with a five-membered NBN ring and pyrene-B (1,8-diaminonaphthalene) with a six-membered NBN ring show differing luminescence. Pyrene-B (o-phenylenediamine) shows concentration-dependent luminescence and enhanced emission after grinding at solid state. Pyrene-B (1,8-diaminonaphthalene) exhibits a turn-on type luminescence upon fluoride ion addition at lower concentration, as well as concentration-dependent stability. Further potential applications of Pyrene-B (o-phenylenediamine) on artificial light-harvesting film were demonstrated by using commercial NiR dye as acceptor.

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Section: Resultsmentioning

confidence: 99%

Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons

Xiao

Sun

et al. 2022

Molecules

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“…15,16 Owing to the unique properties of materials, most researchers have realized innovative photoluminescence materials that rely on the combination of luminophores and polymers by doping and polymerization. [17][18][19][20][21] Thus, the application of specific polymers has become prominent in the area of photoluminescence materials. [22][23][24] Luminophores has undoubtedly created more possibilities regarding the assistance of polymer systems.…”

Section: Introductionmentioning

confidence: 99%

Polymer-Stretching Photoluminescent Regulation by Doping a Single Fluorescent Molecule

Jiang

et al. 2022

CCS Chem

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Photoluminescence materials play an inseparable role in the application of polymer systems. However, intrinsic polymer systems have rarely been intuitively interpreted based on photoluminescence regulation. A novel photoluminescence mechanism called vibration-induced emission (VIE) has recently drawn great attention due to its multicolor fluorescence from a single molecular entity. Based on the unique fluorescent properties of VIE molecules, we have doped 9,14-diphenyl-9,14-dihydrodibenzo[a,c]-phenazine (DPAC) and its derivative DPAC-CN in two stretchable polymers, poly(ε-caprolactone) and ethylene vinyl acetate (EVA) copolymer, to explore the important relationship between luminophores and polymer systems. This research focuses on the multicolor photoluminescence of the obtained blend films that resulted from stretching exertions and temperature responses. The successive conformational alterations of VIE molecules endow continuous photoluminescent changes. Meanwhile, the multicolor variations also provide specific visual evidence regarding the amplified tensile stresses and microstructural changes in the polymer. This demonstration therefore provides advantageous insights into the development of functional optical materials.

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“…Compared with the akin Grignard reaction, which progresses by two steps, the Barbier reaction exhibits advantages including one-pot preparation, broadly applicable metals, and the tolerance to moisture and various functional groups. Recently, we successfully applied the Barbier reaction to polymerization methodology and developed a Barbier polymerization method, through C–C bond formation with carbonyls as electrophiles (Scheme A). − Through one-pot Barbier polymerization, alcohol-containing polymers exhibiting interesting polymerization-induced emission properties, which are hard to prepare through other traditional polymerization methodologies, have been synthesized from nonemissive monomers. Nitro and nitroso groups have played significant roles in organic chemistry and their compounds are widely available.…”

Section: Introductionmentioning

confidence: 99%

Barbier-Type Nitro/Nitroso Addition Polymerization as a Versatile Approach for Molecular Design of Polyarylamines through C–N Bond Formation

Shi

et al. 2021

Macromolecules

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The doping of a polymer chain with nitrogen is an efficient strategy to endow polymer materials with functionality. However, the molecular design of polyarylamines through direct C−N bond formation is still challenging. Herein, a novel polymerization method, named Barbier-type nitro/nitroso addition polymerization, is reported as a versatile approach for molecular design of polyarylamines through C−N bond formation, by utilizing electrophilic nitro/nitroso groups as polymerizable groups. Through Barbier-type nitro/nitroso addition polymerization, a series of polyarylamines have been prepared, including orthopolyaniline, para-polyaniline, meta-polyaniline, para-polymethylaniline, and polynaphthylamine, most of which are hard to be synthesized by current other polymerization methods. By introducing the Barbier-type nitro/nitroso addition into polymer chemistry, the polymerization methodology, monomer, and polymer libraries of polymer chemistry are expanded and a novel avenue is opened up for molecular design of nitrogen-containing polymer materials through direct formation of a C−N bond.

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The introduction of the Barbier reaction into polymer chemistry

Cited by 61 publications

References 32 publications

Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons

Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons

Polymer-Stretching Photoluminescent Regulation by Doping a Single Fluorescent Molecule

Barbier-Type Nitro/Nitroso Addition Polymerization as a Versatile Approach for Molecular Design of Polyarylamines through C–N Bond Formation

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