Colorimetric Ion Sensors Based on Polystyrenes Bearing Side Chain Triazole and Donor-Acceptor Chromophores

Li, Yongrong; Hyakutake, Tsuyoshi; Michinobu, Tsuyoshi

doi:10.2116/analsci.33.599

Cited by 13 publications

(12 citation statements)

References 33 publications

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“…[102] Thes ubsequent reaction with TCNE and TCNQ quantitatively yielded the corresponding new polystyrene derivatives bearing the push-pull chromophores P1 and P2,respectively. [104,105] According to the principle of hard and soft acids and bases (HSAB), the hard basic aniline nitrogen atoms interacted with hard acidic metal ions,s uch as Fe 3+ ,w hile the soft basic cyano nitrogen atoms selectively captured the soft, acidic Ag + metal ion. [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.…”

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

confidence: 99%

“…In addition, all these polystyrene derivatives showed very specific colorimetric ion-sensing behaviors. [104,105] According to the principle of hard and soft acids and bases (HSAB), the hard basic aniline nitrogen atoms interacted with hard acidic metal ions,s uch as Fe 3+ ,w hile the soft basic cyano nitrogen atoms selectively captured the soft, acidic Ag + metal ion. The former interaction decreased the CT absorption band intensity,thereby resulting in decolorization.…”

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

confidence: 99%

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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%

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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“…Upon the completion of electric poling, the second-order nonlinear optical responses of the polymer films were observed. Furthermore, all these polystyrene-based electron donor-acceptor nonconjugated polymers exhibited very specific colorimetric ion sensing behaviors [73][74][75][76]. The hard basic aniline nitrogen atoms preferred to interact with hard acidic metal ions like Fe 3+ , leading to the decrease in the charge-transfer absorption band and thereby resulting in decolorization.…”

Section: Side-chain Electron Donor-acceptor Nonconjugated Polymersmentioning

confidence: 99%

Electron Donor-Acceptor Organic Polymers by “Click” Type Cycloaddition/Retroelectrocyclization Reaction

Huang¹

2020

Organic Polymers

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The "click" type cycloaddition/retroelectrocyclization reaction is an intriguing approach for synthesizing electron donor-acceptor organic polymers. This chapter covers the fundamental reaction mechanism and the basic principles of applying this reaction to the synthesis of organic polymers via postfunctionalization or step-growth polymerization. The electron donor-acceptor moieties can be incorporated into the main-chain and/or side-chain of both conjugated and nonconjugated polymers. These polymers feature attractive properties including intramolecular charge-transfer bands, nonlinear optical properties, redox activities, third-order nonlinear optical properties, and enhanced thermal stability. Because of this, these polymers have found a variety of applications such as colorimetric chemosensors of metal ions, nonlinear optics, and solar cells. This novel "click" chemistry paves a unique path toward the synthesis of next-generation functional materials that cannot be accomplished by the incumbent synthetic methods.

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“…The survey suggested that the metal ion recognition behavior follows the theory of hard and soft acids and bases (HSAB). 92 In other words, hard acidic metal ions led to a decrease in the CT bands due to the recognition by the aniline nitrogen, whereas soft acidic metal ions caused a bathochromic shift in the CT bands due to the recognition by the cyano nitrogen. Although there were slight differences, the overall recognition behaviors of the double clicked polymers P30 and P31 were consistent with those of the previously reported clicked polymers P23 and P24.…”

Section: +mentioning

confidence: 99%

“…The double clicked polystyrene derivatives P30 and P31 exhibited the same anion sensing results albeit with slower reaction rates. 92 Taking into account the global environmental problems, the selective detection of the CN ¹ , F ¹ , and I ¹ ions is practically important. It was concluded that the D-A chromophores are suitable for the chemodosimeter approach, and the order of the sensitivity is CN ¹ > F ¹ > I ¹ .…”

Section: +mentioning

confidence: 99%

Polymeric Chemosensors: A Conventional Platform with New Click Chemistry

Wang

Michinobu

2017

Bulletin of the Chemical Society of Japan

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Polymers are a good platform for the production of various functional materials, since functional moieties can be introduced into both the main chain backbone and side chain pendants by elegant molecular design and utilizing efficient synthetic protocols. Highly colored and fluorescent π-systems have often been employed as ion sensing units especially when heteroaromatic rings are included. The heteroaromatic rings can form supramolecular complexes with metal ions or anions, resulting in the visual color changes of absorption and fluorescence. Conjugated polymers have been traditionally employed to this end, because they are highly emissive and very sensitive to various ions. However, most of such conjugated polymers are synthesized by costly cross-coupling polycondensations, which do not meet the green chemistry concepts of this century. Click chemistry is a new concept representing an efficient and atom-economic synthesis, and one of the most common reactions is the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) yielding 1,2,3-triazole rings. The 1,2,3-triazole derivatives are electronically almost inert, but they possess fluorescent chemosensor properties. Recent examples of polymeric chemosensors based on the 1,2,3-triazole derivatives are introduced. Furthermore, an emerging click chemistry reaction, i.e., the alkyne-acceptor click chemistry, is also introduced. This reaction produces highly colored donor-acceptor (D-A) chromophores on a polymer platform, enabling visual detection of the ion sensing behavior. The polymeric chemosensors with the D-A chromophores show a specific discrimination between hard and soft metal ions by different color changes. These polymers are also useful for anion sensing.

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Colorimetric Ion Sensors Based on Polystyrenes Bearing Side Chain Triazole and Donor-Acceptor Chromophores

Cited by 13 publications

References 33 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

Electron Donor-Acceptor Organic Polymers by “Click” Type Cycloaddition/Retroelectrocyclization Reaction

Polymeric Chemosensors: A Conventional Platform with New Click Chemistry

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