Synthesis of a novel poly(aryl ether) with pendent N-phenylimide groups

Suh, Dong Hack; Chung, Eun Young; Hong, Young Taik; Choi, Kil‐Yeong

doi:10.1002/(sici)1522-9505(19980201)254:1<33::aid-apmc33>3.0.co;2-v

Cited by 12 publications

(1 citation statement)

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“…The starting materials 3,6-dibromopyromellitic dianhydride 25 ( 1 ) and 2-decyl-1-tetradecyl amine 26 ( 2 ) were prepared according to the reported procedures. 1 and 2 were reacted at room temperature in dry THF solution to form the amic acid, and consequently treated with NaOAc and Ac 2 O to give N,N′-bis(2-decyltetradecyl)-3,6-dibromopyromellitic diimide ( 3 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors

et al. 2011

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A highly soluble pyromellitic diimide-based polymer was obtained through imidization polymerization. The novel architecture features diimide subunits linked alternately at 3-6 and N,N′ positions. The polymer is highly transparent in the near ultraviolet-visible regions. Smooth and uniform thin-films were obtained through spin-coating even after blending the polymer with PCBM in 1:9 polymer:PCBM weight ratio. While the polymer itself has modest electron mobility in typical bottom-gate top-contact OFETs, an electron mobility of 3 × 10−3 cm2V−1s−1 was achieved for the blend, which increased to 10−2 cm2V−1s−1 on exposure to propylamine. Thus, polyimides are demonstrated as promising binder materials for solution-processible n-channel semiconductor blends, of which very few examples are known.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors

et al. 2011

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Halogen‐Bonded Assemblies of Arylene Imides and Diimides: Insight from Electronic, Structural, and Computational Studies

Mandal

Bansal

Kumar

et al. 2020

Chemistry A European J

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Halogen‐bonding interactions in electron‐deficient π scaffolds have largely been underexplored. Herein, the halogen‐bonding properties of arylene imide/diimide‐based electron‐deficient scaffolds were studied. The influence of scaffold size, from small (phthalimide) to moderately sized (pyromellitic diimide or naphthalenediimides) to large (perylenediimide), axial‐group modification, and number of halo substituents on the halogen bonding and its self‐assembly was probed in a set of nine compounds. The structural modification leads to tunable optical and redox properties. The first reduction potential E1/21 ranges between −1.09 and −0.17 V (vs. SCE). Two of the compounds, that is, 6 and 9, have deep‐lying LUMOs with values reaching −4.2 eV. Single crystals of all nine systems were obtained, which showed Br⋅⋅⋅O, Br⋅⋅⋅Br, or Br⋅⋅⋅π halogen‐bonding interactions, and a few systems are capable of forming all three types. These interactions lead to halogen‐bonded rings (up to 12‐membered), which propagate to form stacked 1D, 2D, or corrugated sheets. A few outliers were also identified, for example, molecules that prefer C−H⋅⋅⋅O hydrogen bonding over halogen bonding, or noncentrosymmetric rather than centrosymmetric organization. Computational studies based on Atoms in Molecules and Natural Bond Orbital analysis provided further insight into the halogen‐bonding interactions. This study can lead to a predictive design tool‐box to further explore related systems on surfaces reinforced by these weak directional forces.

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Co‐poly(aryl ether sulfone)s containing phthalimidine moiety in the main chain

Ghosh¹,

Maji²,

Banerjee³

et al. 2011

Polymers for Advanced Techs

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Several new co‐poly(arylene ether sulfone)s have been prepared by the reaction of 4,4′‐fluorodiphenyl sulfone (FDS) with different bisphenols namely 4,4′‐isopropylidenediphenol (BPA), 4,4′‐hexafluoroisopropylidenediphenol (6F‐BPA), and N‐phenyl‐3,3‐bis(4‐hydroxyphenyl)phthalimidine(PA). The homo‐poly(arylene ether sulfone)s are named as 1a, 2a, and 3a. The copolymers namely 2b, 2c, 2d and 3b, 3c, 3d have been prepared, respectively, on reaction of FDS with BPA or 6F‐BPA using different molar ratios of PA such as 25, 50, and 75. The poly(aryl ether sulfone)s 1a containing PA unit in the main chain showed a very high glass transition temperature of 280°C and an outstanding thermal stability up to 510°C for 5% weight loss under synthetic air. Depending on the mole% of PA, the glass transition temperatures of the copolymers can be varied. The polymers were soluble in a wide range of organic solvents. Transparent thin films of these polymers exhibited tensile strengths upto 84 MPa and Young's modulus up to 3.16 GPa. The films of these polymers showed low water absorption of 0.24%. Copyright © 2009 John Wiley & Sons, Ltd.

show abstract

Synthesis of a novel poly(aryl ether) with pendent N-phenylimide groups

Cited by 12 publications

References 11 publications

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors

Halogen‐Bonded Assemblies of Arylene Imides and Diimides: Insight from Electronic, Structural, and Computational Studies

Co‐poly(aryl ether sulfone)s containing phthalimidine moiety in the main chain

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