Electronic properties of isoindigo-based conjugated polymers bearing urea-containing and linear alkyl side chains

Charron, Brynn Petras; Ocheje, Michael U.; Selivanova, Mariia; Hendsbee, Arthur D.; Li, Yuning

doi:10.1039/c8tc03438a

Cited by 24 publications

(26 citation statements)

References 43 publications

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“…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%

“…Rondeau‐Gagné and co‐workers introduced urea groups in the side chains of isoindigo‐based polymers P181–P183 . They show that the charge mobility enhancement is not obvious for these polymers when the contents of urea groups are low.…”

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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“…108 However, designer sidechains possessing hydrogen bonding functional groups, such as amides and ureas, can accomplish more than simply imparting solubility. Hydrogen bonding sidechains can improve interchain packing, solid-state microstructure, and charge transport of both n-type and p-type conjugated polymers, [109][110][111] with amide groups especially useful given the strength of hydrogen bonding between them. [112][113][114][115] An exemplar of this design came in 2018 from Ocheje et al 116 Their family of diketopyrrolopyrrole polymers (Figure 7) possessed amide-containing aliphatic chains that participated in interchain hydrogen bonding throughout the polymer network.…”

Section: Organic Electronicsmentioning

confidence: 99%

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Mullin

Sharber

Thomas

2021

Journal of Polymer Science

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Organic conjugated polymers and oligomers are key electronic materials for applications such as transistors, photovoltaics, and light emitting devices due to their potential for solution processability, mechanical flexibility, and precise structure-based tuning compared to inorganic materials. In dilute environments, the optoelectronic properties of conjugated polymers are largely governed by their constitutional structure and, to a lesser degree, their solution-state intramolecular configuration. In the solid state, intramolecular conformation and intermolecular electronic coupling impact these properties substantially, especially in relation to device performance. Therefore, an increasingly important area of research concerning conjugated materials is developing design strategies aimed at optimizing the solid-state packing for electronic applications. Programming solid-state packing arrangements through discrete non-covalent interactions is an emerging strategy within the context of conjugated polymers. This review focuses on the use of the two most prevalent discrete and directional interactions used to dictate the self-assembly of conjugated polymers and oligomers-hydrogen bonds and chalcogen bonds. We also discuss how these design motifs can imbue conjugated materials with appealing physical properties while simultaneously retaining or improving electronic capabilities.

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“…Charron et al extended this strategy to isoindigo‐based conjugated polymers (Figure 5I,J). 59 The improved nanoscale morphology and the enhancement of average charge mobility observed for P22 confirm that grafting urea moieties in the side chains is an efficient strategy to elevate the performance of polymeric FETs.…”

Section: Improving Charge Mobility Of Conjugated Polymer Via H‐bondingmentioning

confidence: 85%

Incorporation of hydrogen‐bonding units into polymeric semiconductors toward boosting charge mobility, intrinsic stretchability, and self‐healing ability

Cheng

Gao

et al. 2021

SmartMat

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The soft nature has endowed conjugated polymers with promising applications in a wide range of field‐effect transistor (FET) based flexible electronics. With unremitting efforts on revealing the molecular structure–property relationships, numerous novel conjugated polymers with high mobility and excellent mechanical property have been developed in the past decades. Incorporating hydrogen‐bonding (H‐bonding) units into semiconducting polymers is one of the most successful strategies for designing high‐performance semiconducting materials. In this review, we aim to highlight the roles of H‐bonding units in the performances of polymeric FETs from three aspects. These include (i) charge mobility enhancement for semiconducting polymers after incorporation of H‐bonding units into the side chains, (ii) the effects of H‐bonding units on the stretchability of conjugated polymers, and (iii) the improvement of self‐healing properties of conjugated polymers containing dynamic hydrogen bonds due to the H‐bonding units in the side chains or conjugated backbones.

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Electronic properties of isoindigo-based conjugated polymers bearing urea-containing and linear alkyl side chains

Abstract: A side-chain engineering study has been performed with isoindigo-based conjugated polymers to modulate their physical and electronic properties through the incorporation of urea-containing and saturated linear side chains.

Cited by 24 publications

References 43 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

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Incorporation of hydrogen‐bonding units into polymeric semiconductors toward boosting charge mobility, intrinsic stretchability, and self‐healing ability

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