Unraveling the Main Chain and Side Chain Effects on Thin Film Morphology and Charge Transport in Quinoidal Conjugated Polymers

Liu, Xuncheng; He, Bo; Garzón‐Ruiz, Andrés; Navarro, Amparo; Chen, Teresa L.; Kolaczkowski, Matthew A.; Feng, Shizhen; Zhang, Lianjie; Anderson, Christopher L.; Chen, Junwu; Liu, Yi

doi:10.1002/adfm.201801874

Cited by 62 publications

(81 citation statements)

References 42 publications

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“…This is because side chains attached to the DPP moiety can fold into the extra space created by less bulky thiophene units between DPP building blocks (Scheme S2, Supporting Information). A similar observation was reported previously in other conjugated polymer systems . The FWHM for the (100) peak increased with the number of thiophene units or the size of fused thiophene rings, which indicated a reduction in the polymer crystallite size.…”

Section: Resultssupporting

confidence: 89%

“…First, the degree of crystallinity and molecular packing lattice parameter in the crystalline region of five DPP thin films were measured by GIWAXS, before and after thermal annealing. [65,66] The FWHM for the (100) peak increased with the number of thiophene units or the size of fused thiophene rings, which indicated www.advelectronicmat.de a reduction in the polymer crystallite size. The 2D scattering patterns and the 1D line-cut profiles (both in plane and out of plane scattering profile) were shown in Figure 3 for annealed films and Figure S9 for as-cast films in the Supporting Information, respectively.…”

Section: The Relationship Between Mechanical Properties and Morphologymentioning

confidence: 99%

“…[66] As shown in Figure 5, the T g of two polymers (PA3T-BC2-C10C12 and PA4T-BC2-C10C12) with increased number of backbone thiophene units were compared. [66] As shown in Figure 5, the T g of two polymers (PA3T-BC2-C10C12 and PA4T-BC2-C10C12) with increased number of backbone thiophene units were compared.…”

Section: Influence Of the Thiophene Block On The Backbone T Gmentioning

confidence: 99%

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The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers

Song

Ocheje

Huang

et al. 2019

Adv Elect Materials

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102

155

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Organic semiconducting donor–acceptor polymers are promising candidates for stretchable electronics owing to their mechanical compliance. However, the effect of the electron‐donating thiophene group on the thermomechanical properties of conjugated polymers has not been carefully studied. Here, thin‐film mechanical properties are investigated for diketopyrrolopyrrole (DPP)‐based conjugated polymers with varying numbers of isolated thiophene moieties and sizes of fused thiophene rings in the polymer backbone. Interestingly, it is found that these thiophene units act as an antiplasticizer, where more isolated thiophene rings or bigger fused rings result in an increased glass transition temperature (Tg) of the polymer backbone, and consequently elastic modulus of the respective DPP polymers. Detailed morphological studies suggests that all samples show similar semicrystalline morphology. This antiplasticization effect also exists in para‐azaquinodimethane‐based conjugated polymers, indicating that this can be a general trend for various conjugated polymer systems. Using the knowledge gained above, a new DPP‐based polymer with increased alkyl side chain density through attaching alky chains to the thiophene unit is engineered. The new DPP polymer demonstrates a record low Tg, and 50% lower elastic modulus than a reference polymer without side‐chain decorated on the thiophene unit. This work provides a general design rule for making low‐Tg conjugated polymers for stretchable electronics.

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Section: Resultssupporting

confidence: 89%

Section: The Relationship Between Mechanical Properties and Morphologymentioning

confidence: 99%

Section: Influence Of the Thiophene Block On The Backbone T Gmentioning

confidence: 99%

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The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers

Song

Ocheje

Huang

et al. 2019

Adv Elect Materials

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102

155

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“…It is noted that the odd–even trend fails when the spacer groups are longer than –(C 6 H 12 ) for P91 – P93 . Such an odd–even effect of the branching point on the chain packing, morphology, and charge transporting performance has also been demonstrated by Liu and co‐workers with the quinoidal para ‐azaquinodimethane‐based conjugated polymers P102 – P105 …”

Section: Alkyl Chains With Different Structuresmentioning

confidence: 57%

“…Branching alkyl chains are usually attached to the donor and/or acceptor moieties of conjugated D–A polymers to improve their solubilities in organic solvents. Many groups have investigated the effect of the branching point position of branching alkyl chain on the solid state structures and charge transporting behaviors of conjugated polymers ( Scheme ) . In most cases, the polymer backbones become more planar, and the interchain packing and charge mobilities are improved after moving the branching points away from the backbones.…”

Section: Alkyl Chains With Different Structuresmentioning

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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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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Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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Unraveling the Main Chain and Side Chain Effects on Thin Film Morphology and Charge Transport in Quinoidal Conjugated Polymers

Cited by 62 publications

References 42 publications

The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers

The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers

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

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

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