Effects of click postfunctionalization on thermal stability and field effect transistor performances of aromatic polyamines

Michinobu, Tsuyoshi; Seo, Chayeon; Noguchi, Keiichi; Mori, Takehiko

doi:10.1039/c2py20079a

Cited by 26 publications

(19 citation statements)

References 75 publications

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“…When the side-chain alkynes of aromatic polyamine P14 were functionalized by the CA-RE reaction with TCNE, the desired amount of electron-accepting TCBD units could be introduced into the polymer.Accordingly,the frontier orbital energy levels of the resulting polyamine P15 were controlled by the added TCNE amount. [112] As expected, the ptype characteristics were weakened when the TCBD moiety was formed at the side chains of P15.T hus,t he p-type TFT performance could not be detected when x exceeded 0.5, but no n-type TFT behavior was evident. [111] TheL UMO level, estimated from the E red,1 value,reached À4.2 eV when the TCBD amount (x) was 1.…”

Section: Low-bandgap Semiconducting Polymers By Ca-re Click Postfuncsupporting

confidence: 60%

“…Theprecursor polyamine P14 displayed at ypical p-type TFT behavior with ah ole mobility (m h )ofabout 10 À3 cm 2 V À1 s À1 . [112] As expected, the ptype characteristics were weakened when the TCBD moiety was formed at the side chains of P15.T hus,t he p-type TFT performance could not be detected when x exceeded 0.5, but no n-type TFT behavior was evident. This was probably due to the decreased intermolecular interactions caused by the nonplanar bulky TCBD moieties.T he n-type operation of P15 (x = 1) films could be eventually demonstrated by the resistive digital memory characteristics.…”

Section: Low-bandgap Semiconducting Polymers By Ca-re Click Postfuncsupporting

confidence: 60%

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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: Low-bandgap Semiconducting Polymers By Ca-re Click Postfuncsupporting

confidence: 60%

Section: Low-bandgap Semiconducting Polymers By Ca-re Click Postfuncsupporting

confidence: 60%

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

2018

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“…For example, the increment in the glass transition temperature was 27°C, while the increase in the thermal degradation temperature was 118°C for P16. These authors successfully fabricated thin film transistors based on P16 and P17 and established a clear correlation between the polymer energy levels and hole mobilities [63]. By using a similar strategy, a triphenylaminebased conjugated polymer (P18) with cyano-containing chromophore in the side chain was synthesized and used for probing Hg 2+ ion.…”

Section: Side-chain Electron Donor-acceptor Conjugated 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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“…Das Vorstufen‐Polyamin P14 zeigte ein typisches TFT‐Verhalten vom p‐Typ mit einer Lochmobilität ( μ h ) von ca. 10 −3 cm 2 V −1 s −1 . Wie erwartet wurden die p‐Typ‐Eigenschaften abgeschwächt, wenn die TCBD‐Einheiten an den Seitenketten von P15 gebildet wurden.…”

Section: Die Ca‐re‐reaktion In Der Polymerchemieunclassified

Die [2+2]‐Cycloadditions‐Retroelektrocyclisierungs(CA‐RE)‐Klick‐Reaktion: ein einfacher Zugang zu molekularen und polymeren Push‐pull‐Chromophoren

Michinobu

Diederich

2018

Angewandte Chemie

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Die [2+2]‐Cycloadditions‐Retroelektrocyclisierungs(CA‐RE)‐Reaktion von elektronenreichen Alkinen mit elektronenarmen Alkenen ist ein effizientes Verfahren zur Bildung nichtplanarer Donor‐Akzeptor‐Chromophore sowohl in molekularen als auch in polymeren Plattformen. Diese Chromophore zeigen ansprechende Eigenschaften, wie intramolekulare Charge‐Transfer(ICT)‐Banden, nichtlineare optische Eigenschaften und Redox‐Eigenschaften zur Verwendung in elektronischen und optoelektronischen Funktionseinheiten der nächsten Generation. Dieser Aufsatz fasst die Entwicklung der CA‐RE‐Reaktion zusammen, beginnend mit den anfänglichen Berichten über Organometallverbindungen bis hin zu rein organischen Systemen. Die strukturellen Voraussetzungen für schnelle Umsetzungen in hohen Ausbeuten, Merkmale echter Klick‐Chemie, werden anhand von Beispielen dargelegt, die die breiten möglichen Alkin‐ und Alkensubstitutionsmuster belegen. Die CA‐RE‐Klick‐Reaktion wurde erfolgreich in der Polymerchemie eingesetzt. Die gebildeten polymeren Push‐pull‐Chromophore finden dabei zahlreiche interessante Anwendungen.

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Effects of click postfunctionalization on thermal stability and field effect transistor performances of aromatic polyamines

Cited by 26 publications

References 75 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

Die [2+2]‐Cycloadditions‐Retroelektrocyclisierungs(CA‐RE)‐Klick‐Reaktion: ein einfacher Zugang zu molekularen und polymeren Push‐pull‐Chromophoren

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