Multi-coloration of polyurethane derivatives through click postfunctionalization, electrochemical oxidation, and Ag+ ion complexation

Li, Yongrong; Michinobu, Tsuyoshi

doi:10.1039/c2jm30298e

Cited by 21 publications

(15 citation statements)

References 78 publications

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“…[103] It should be noted that both click reactions proceeded rapidly without any side reactions and carrying out the reactions in the reverse order also gave the same products. [106] Thealkyne side chains of P5 reacted with TCNE and TCNQ to yield orange-colored P6 and green-colored P7,r espectively.T he colors of these postfunctionalized polyurethane derivatives could be further changed to magenta and yellowish-green by complexation with Ag + ions.M oreover,t he electrochemical oxidation of the precursor polyurethane P5 at >+ 0.25 V (versus Ag/AgCl in MeCN) gave ablue polymer,whose color is ascribed to the formation of aromatic amine-based radical cations.S ince the primary colors of red, yellow,b lue,a nd magenta were created from the single precursor polymer, almost all colors could be produced by this approach. Thesecond-order NLO responses of the P3 and P4 films were investigated after electric poling.…”

Section: Side-chain Postfunctionalization Of Polymers By the Ca-re Rementioning

confidence: 99%

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

2018

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The [2+2] cycloaddition-retroelectrocyclization (CA-RE) reaction between electron-rich alkynes and electron-deficient alkenes is an efficient procedure to create nonplanar donor-acceptor (D-A) chromophores in both molecular and polymeric platforms. They feature attractive properties including intramolecular charge-transfer (ICT) bands, nonlinear optical properties, and redox activities for use in next-generation electronic and optoelectronic devices. This Review summarizes the development of the CA-RE reaction, starting from the initial reports with organometallic compounds to the extension to purely organic systems. The structural requirements for rapid, high-yielding transformations with true click chemistry character are illustrated by examples that include the broad alkyne and alkene substitution modes. The CA-RE click reaction has been successfully applied to polymer synthesis, with the resulting polymeric push-pull chromophores finding many interesting applications.

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Section: Side-chain Postfunctionalization Of Polymers By the Ca-re Rementioning

confidence: 99%

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

2018

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“…The color of the cross‐linked polymer films in the neutral state is caused by the strong intramolecular CT interaction at the cross‐linking points. It was previously shown that similar CT chromophores produced by the [2+2] CA‐RE reaction could recognize both protic acids and Lewis acids . In particular, the soft Lewis acidic Ag + ions were selectively recognized in terms of the multiple coordination to the 3‐4 cyano groups of the CT chromophore leading to a well‐defined color change.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial Polymeric Films Fabricated by [2+2] Cycloaddition–Retroelectrocyclization and Ag⁺ Ion Coordination

Fujita

Nihei²,

Bito³

et al. 2018

Macromolecular Bioscience

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The [2+2] cycloaddition–retroelectrocyclization (CA–RE) between N,N‐dialkylaniline‐substituted alkynes and 7,7,8,8‐tetracyanoquinodimethane (TCNQ) is employed to fabricate functional cross‐linked polymer films containing the intramolecular charge‐transfer (CT) chromophores at the cross‐linking points. Polystyrene bearing N,N‐dialkylaniline‐substituted alkynes (P1) and TCNQ polyester (P2) are mixed in tetrahydrofuran (THF), then this solution is spray‐coated onto an indium tin oxide or glass plate. Heating to 100 °C initiates the [2+2] CA‐RE reaction, resulting in the formation of cross‐linked polymer films. The reaction progress and completion are evaluated by monitoring the CT absorption band and cyano vibration peaks. The resulting cross‐linked polymer films show reversible cathodic electrochromism between the neutral and anion radical states. In addition, they also display the visual detection behavior of protic acids and Lewis acids, such as Ag+ ions. Accordingly, the Ag+ ion‐loaded polymer films are prepared, and their antibacterial activities are studied. As more Ag+ ions are loaded, the CT band more bathochromically shifts and more potent antibacterial activities are obtained. Therefore, the antibacterial activity of the polymer films can be visually recognized by the film colors. Furthermore, the loaded Ag+ ions can be released from the polymer films by application of an electrochemical potential.

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“…45 In order to reveal the electrochemical properties and estimate their energy levels, electrochemical measurements were performed. 45 In order to reveal the electrochemical properties and estimate their energy levels, electrochemical measurements were performed.…”

Section: Electrochemistrymentioning

confidence: 99%

Facile synthesis of functional poly(vinylene sulfide)s containing donor–acceptor chromophores by a double click reaction

et al. 2016

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aThe new electronically active poly(vinylene sulfide)s containing the dialkylaniline-substituted electron-rich alkynes in the side chains were designed and synthesized by the 'thiol-click' polymerization. Subsequently, the donor-acceptor chromophores were introduced into the side chains of the polymer by the [2+2] click reaction as an efficient postfunctionalization method. The polymers showed good solubility in common organic solvents and the high thermal stability. The photophysical and electrochemical properties, as well as the click reactions, were characterized by means of UV-vis absorption spectroscopy, cyclic voltammetry, ect. After the introduction of donor-acceptor chromophores, the polymer showed a strong charge-transfer (CT) band in the visible absorption region, potent redox activities and a narrow band gap compared with the precursors. In addition, the third-order nonlinear properties, including the nonlinear absorption and the nonlinear susceptibilities, were investigated by using Z-scan techniques. A typical saturable absorption behavior was observed for the third order nonlinear absorption, with the nonlinear absorption coefficients (β) values of the polymer being -9.0×10 -12 m/W. Please do not adjust marginsPlease do not adjust margins click'), and the whole conjugated structures for main chains were designed. We hope better NLO properties because of the longer conjugated structures, but the similar results were obtained here. It was suggested that the moieties from [2+2] click reagents affected greater than those of conjugated structures.

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Multi-coloration of polyurethane derivatives through click postfunctionalization, electrochemical oxidation, and Ag+ ion complexation

Cited by 21 publications

References 78 publications

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

Antibacterial Polymeric Films Fabricated by [2+2] Cycloaddition–Retroelectrocyclization and Ag⁺ Ion Coordination

Facile synthesis of functional poly(vinylene sulfide)s containing donor–acceptor chromophores by a double click reaction

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Multi-coloration of polyurethane derivatives through click postfunctionalization, electrochemical oxidation, and Ag+ ion complexation

Cited by 21 publications

References 78 publications

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

Antibacterial Polymeric Films Fabricated by [2+2] Cycloaddition–Retroelectrocyclization and Ag+ Ion Coordination

Facile synthesis of functional poly(vinylene sulfide)s containing donor–acceptor chromophores by a double click reaction

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Product

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Antibacterial Polymeric Films Fabricated by [2+2] Cycloaddition–Retroelectrocyclization and Ag⁺ Ion Coordination