Controlling the gate dielectric properties of vinyl-addition polynorbornene copolymers<i>via</i>thiol–ene click chemistry for organic field-effect transistors

Kim, Myung-Jin; Park, Hyunjin; Ha, Jinha; Ho, Linh Nguyet Thi; Kim, Eun Chae; Lee, Woohwa; Park, Sung Min; Won, Jong Chan; Kim, Dong-Gyun; Kim, Yun Ho; Kim, Yong Seok

doi:10.1039/d1tc00283j

Cited by 13 publications

(17 citation statements)

References 43 publications

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“…The overall results are compiled in Table . There have been some reports about the vinyl-addition polymerization of n -alkyl-substituted NBs using diverse palladium catalyst systems, but the preparation of NB/ n -alkyl-substituted NBs copolymers with various monomer contents using these catalytic system has not been considered. ,− In our previous study, the Pd 2 (dba) 3 /PCy 3 /Li[FABA] system had shown efficient copolymerization of NB with 5-vinyl-2-norborene, which produced the copolymers with the high molecular weights in high yields and showed a similar composition of the copolymer to the monomer feed ratio . Thus, we applied this three-component catalyst system to the copolymerization of NB and NBC x with varying monomer contents.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Vinyl-Addition Polynorbornene Copolymers Bearing Pendant n-Alkyl Chains and Systematic Investigation of Their Properties

Kim

et al. 2021

Macromolecules

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The synthesis of vinyl-addition polynorbornene copolymers bearing pendant n-alkyl chains (octyl, decyl, and dodecyl groups) and systematic investigation of their properties are reported. Vinyl-addition polymerization using Pd2(dba)3/PCy3/Li[FABA] produces poly(norbornene-co-5-n-alkyl-2-norbornene)s, P(NB/NBCx) (x is the number of carbon atoms in the n-alkyl chain), with a high weight-average molecular weight (M w) of 71.2–410.6 kDa, high yields of 68–87%, and a similar monomer content to the monomer feed ratio. The films of the resulting copolymers are successfully prepared by a solution-casting method. The glass transition temperature (T g) of these films can be tuned from 91.7 to 192.4 °C depending on the length of the alkyl chain of NBCx and the NBCx content. The mechanical properties are controlled by these two parameters as well. The change from brittle to ductile properties is observed with the increasing NBCx content of P(NB/NBCx) films, where the increase in the length of the alkyl chain of NBCx increases the value of the strain at break, accompanied by a decrease in strength. The wide-angle X-ray scattering analysis provides information on nanostructure–property relationships in copolymers. All P(NB/NBCx) films display a high transmittance of more than 85% in the visible-light range.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Vinyl-Addition Polynorbornene Copolymers Bearing Pendant n-Alkyl Chains and Systematic Investigation of Their Properties

Kim

et al. 2021

Macromolecules

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“…Other VA-PNBs that could be easily subjected to further functionalization would be those with pendant double bonds. If the polymerization of an alkenyl-substituted norbornene proceeds selectively through the endocyclic double bond, the exocyclic pendant double bond is a versatile group for its transformation into other functional groups by addition reactions, [18][19][20] epoxidation, 19,21,22 cyclopropanation, 19 etc. 23,24 Particularly, alkenyl-monomers with a terminal unsaturation, such as the accessible and commercially available 5-vinyl-2norbornene (VNB), are especially interesting.…”

Section: Introductionmentioning

confidence: 99%

Vinylic addition poly(norbornene-co-alkenylnorbornenes) synthesized with benzylic palladium catalysts: materials for manifold functionalization

Pérez-Ortega

Albéniz

2022

Polym. Chem.

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“…Instruments and Characterization. 1 H, 13 C, and 19 F nuclear magnetic resonance (NMR) spectra were recorded at room temperature (ca. 25 °C) using a Bruker Ascend 400 MHz NMR spectrometer.…”

Section: ■ Introductionmentioning

confidence: 99%

Bis(β-ketoimino)nickel(II) Complexes for Random Copolymerization of Norbornene and Methyl 5-Norbornene-2-carboxylate with Controlled Ester Group Incorporation

Chae

Park

et al. 2022

Macromolecules

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A series of bis(β-ketoimino)nickel(II) complexes with p-substituted N-phenyl groups, Ni[CH 3 C(O)CHC(NPhR)-CH 3 ] 2 (Ni1: R = −OCH 3 ; Ni2: R = −CH 3 ; Ni3: R = −CF 3 ), were synthesized, and their general coordination geometry was elucidated by single-crystal X-ray diffraction analysis of Ni3. These complexes were paired with tris(pentafluorophenyl)borane (B(C 6 F 5 ) 3 ) to catalyze the vinyl addition copolymerization of norbornene (NB) and methyl 5-norbornene-2-carboxylate (NBE). All the catalyst systems exhibited high catalytic activities (>10 5 g polymer mol Ni −1 h −1 ) at NBE feed contents of up to 50 mol %, resulting in the production of copolymers with high molecular weights (M w = 135−355 kg mol −1 , Đ = 1.78−2.12). In addition, the content of polar ester groups was precisely controlled by the feed ratio of the monomers. For Ni3, two monomer reactivity ratios were found to be close to unity (Fineman−Ross method: r NB = 0.951, r NBE = 0.903; Kelen−Tudos method: r NB = 1.15, r NBE = 0.978). Since the copolymerization behaviors were revealed to be independent of the electronegativity of p-substituent, all the catalyst systems of Ni1−Ni3/B(C 6 F 5 ) 3 were considered to serve the random copolymerization of NB and NBE. The resulting poly(norbornene-random-methyl 5-norbornene-2-carboxylate)s exhibited the dielectric and surface properties well tunable by compositional modulation.

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Controlling the gate dielectric properties of vinyl-addition polynorbornene copolymersviathiol–ene click chemistry for organic field-effect transistors

Abstract: The control of gate dielectric properties of vinyl-addition polynorbornene copolymers bearing pendant vinyl groups for OFET applications is demonstrated through photoinitiated thiol–ene click chemistry.

Cited by 13 publications

References 43 publications

Synthesis of Vinyl-Addition Polynorbornene Copolymers Bearing Pendant n-Alkyl Chains and Systematic Investigation of Their Properties

Synthesis of Vinyl-Addition Polynorbornene Copolymers Bearing Pendant n-Alkyl Chains and Systematic Investigation of Their Properties

Vinylic addition poly(norbornene-co-alkenylnorbornenes) synthesized with benzylic palladium catalysts: materials for manifold functionalization

Bis(β-ketoimino)nickel(II) Complexes for Random Copolymerization of Norbornene and Methyl 5-Norbornene-2-carboxylate with Controlled Ester Group Incorporation

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