Influence of amide-containing side chains on the mechanical properties of diketopyrrolopyrrole-based polymers

Ocheje, Michael U.; Selivanova, Mariia; Song, Zhanqian; Nguyen, Thi Hai Van; Charron, Brynn Petras; Chuang, Ching-Heng; Cheng, Yingduan; Billet, Blandine; Noori, Suendues; Chiu, Yu‐Cheng; Gu, Xiaodan; Rondeau‐Gagné, Simon

doi:10.1039/c8py01207e

Cited by 63 publications

(83 citation statements)

References 42 publications

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“…Notably, P187 , with high contents of amide groups in the side chains still maintain good solubility in organic solvents. They also demonstrated that the introduction of imide groups in the side chains could effectively enhance the mechanical properties of polymers P184–P186 to afford stretchability and morphology healing …”

Section: Side Chains With Heteroatoms and Functional Groupsmentioning

confidence: 99%

“…Hydrogen bonding (H bonding) has been widely used to tune intermolecular interactions and self‐assembly structures by considering its relative bonding strength and directionality . On the basis of this consideration, as shown in Scheme and Figure , some of us incorporated urea groups in the side chains of DPP‐based polymers P175–P177 .…”

Section: Side Chains With Heteroatoms and Functional Groupsmentioning

confidence: 99%

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The Effects of Side Chains on the Charge Mobilities and Functionalities of Semiconducting Conjugated Polymers beyond Solubilities

et al. 2019

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Recent decades have witnessed the rapid development of semiconducting polymers in terms of high charge mobilities and applications in transistors. Significant efforts have been made to develop various conjugated frameworks and linkers. However, studies are increasingly demonstrating that the side chains of semiconducting polymers can significantly affect interchain packing, thin film crystallinity, and thus semiconducting performance. Ways to modify the side alkyl chains to improve the interchain packing order and charge mobilities for conjugated polymers are first discussed. It is shown that modifying the branching chains by moving the branching points away from the backbones can boost the charge mobilities, which can also be improved through partially replacing branching chains with linear ones. Second, the effects of side chains with heteroatoms and functional groups are discussed. The siloxane‐terminated side chains are utilized to enhance the semiconducting properties. The fluorinated alkyl chains are beneficial for improving both charge mobility and air stability. Incorporating H bonding group side chains can improve thin film crystallinities and boost charge mobilities. Notably, incorporating functional groups (e.g., glycol, tetrathiafulvalene, and thymine) into side chains can improve the selectivity of field‐effect transistor (FET)‐based sensors, while photochromic group containing side chains in conjugated polymers result in photoresponsive semiconductors and optically tunable FETs.

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Section: Side Chains With Heteroatoms and Functional Groupsmentioning

confidence: 99%

Section: Side Chains With Heteroatoms and Functional Groupsmentioning

confidence: 99%

The Effects of Side Chains on the Charge Mobilities and Functionalities of Semiconducting Conjugated Polymers beyond Solubilities

et al. 2019

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“…Those potential weak interactions include: π–π interactions, hydrogen bonds, and metal‐ligand coordination bonds. Many weak interaction bonds were successfully designed into conjugated polymers to endow a self‐healing ability into conjugated polymers. Previous works by the Bao group are great examples for demonstrating this capability.…”

Section: Future Lookmentioning

confidence: 99%

Glass Transition Phenomenon for Conjugated Polymers

Qian

Cao

Galuska

et al. 2019

Macro Chemistry & Physics

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Conjugated polymers are emerging as promising building blocks for a broad range of modern applications including skin‐like electronics, wearable optoelectronics, and sensory technologies. In the past three decades, the optical and electronic properties of conjugated polymers have been extensively studied, while their thermomechanical properties, especially the glass transition phenomenon which fundamentally represents the polymer chain dynamics, have received much less attention. Currently, there is a lack of design rules that underpin the glass transition temperature of these semirigid conjugated polymers, putting a constraint on the rational polymer design for flexible stretchable devices and stable polymer glass that is needed for the devices’ long‐term morphology stability. In this review article, the glass transition phenomenon for polymers, glass transition theories, and characterization techniques are first discussed. Then previous studies on the glass transition phenomenon of conjugated polymers are reviewed and a few empirical design rules are proposed to fine‐tune the glass transition temperature for conjugated polymers. The review paper is finished with perspectives on future directions on studying the glass transition phenomena of conjugated polymers. The goal of this perspective is to draw attention to challenges and opportunities of controlling, predicting, and designing polymeric semiconductors, specifically to accommodate their end use.

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“…Nuclear magnetic resonance (NMR) and variable temperature Fourier transform infrared (FT-IR) spectroscopy were taken to ascertain the formation of interchain hydrogen bonds. Compared to the investigation of DPP-based polymers from Simon et al [ 30 ], we further studied the influence of amide-containing proportion on solution gelation, which is also significant for the solution-processed technologies in optoelectronics. Most importantly, we developed a practical method for measuring the intrinsic mechanical properties of thin films taking advantage of the conventional tensile strain instrument (dynamic mechanical analyzer, DMA), which is assisted by a hollow substrate (PMMA).…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Effects of Interchain Hydrogen Bonds on Solution Gelation and Mechanical Properties of Diarylfluorene-Based Semiconductor Polymers

et al. 2020

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The intrinsically rigid and limited strain of most conjugated polymers has encouraged us to optimize the extensible properties of conjugated polymers. Herein, learning from the hydrogen bonds in glucose, which were facilitated to the toughness enhancement of cellulose, we introduced interchain hydrogen bonds to polydiarylfluorene by amide-containing side chains. Through tuning the copolymerization ratio, we systematically investigated their influence on the hierarchical condensed structures, rheology behavior, tensile performances, and optoelectronic properties of conjugated polymers. Compared to the reference copolymers with a low ratio of amide units, copolymers with 30% and 40% amide units present a feature of the shear-thinning process that resembled the non-Newtonian fluid, which was enabled by the interchain dynamic hydrogen bonds. Besides, we developed a practical and universal method for measuring the intrinsic mechanical properties of conjugated polymers. We demonstrated the significant impact of hydrogen bonds in solution gelation, material crystallization, and thin film stretchability. Impressively, the breaking elongation for P4 was even up to ~30%, which confirmed the partially enhanced film ductility and toughness due to the increased amide groups. Furthermore, polymer light-emitting devices (PLEDs) based on these copolymers presented comparable performances and stable electroluminescence (EL). Thin films of these copolymers also exhibited random laser emission with the threshold as low as 0.52 μJ/cm2, suggesting the wide prospective application in the field of flexible optoelectronic devices.

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Influence of amide-containing side chains on the mechanical properties of diketopyrrolopyrrole-based polymers

Abstract: An efficient strategy to modify the mechanical properties of conjugated polymers has been developed through the incorporation of amide moieties.

Cited by 63 publications

References 42 publications

The Effects of Side Chains on the Charge Mobilities and Functionalities of Semiconducting Conjugated Polymers beyond Solubilities

The Effects of Side Chains on the Charge Mobilities and Functionalities of Semiconducting Conjugated Polymers beyond Solubilities

Glass Transition Phenomenon for Conjugated Polymers

Unveiling the Effects of Interchain Hydrogen Bonds on Solution Gelation and Mechanical Properties of Diarylfluorene-Based Semiconductor Polymers

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