Side-Chain Sequence Enabled Regioisomeric Acceptors for Conjugated Polymers

Luo, Xuyi; Tran, Dung T.; Kadlubowski, Natalie M.; Ho, Carr Hoi Yi; Riley, Parand R.; So, Franky; Mei, Jianguo

doi:10.1021/acs.macromol.8b01946

Cited by 15 publications

(16 citation statements)

References 45 publications

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“…Mei and co‐workers reported on P112 , P113, and P114 , in which both the linear and branching alkyl chains are attached to the backbones . They found that the sequence of the arrangement of alkyl chains along the backbone has a significant effect on the aggregation behaviors of polymer chains.…”

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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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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“…[ 29 ] Isoindigo unit can also be replaced by only a thienyl ring to obtain an asymmetric derivative thieno‐benzo‐isoindigo ( M2 ). [ 44,89–91 ] However, M2 ‐based P15 exhibited low OFET performance even though the coplanarity of M2 was much higher than that of isoindigo, due to the face‐on polymer orientation. [ 44 ]…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

“…[29] Isoindigo unit can also be replaced by only a thienyl ring to obtain an asymmetric derivative thieno-benzo-isoindigo (M2). [44,[89][90][91] However, M2-based P15 exhibited low OFET performance even though the coplanarity of M2 was much higher than that of isoindigo, due to the face-on polymer orientation. [44] The electron-rich thiophene ring elevates the LUMO energy level of M1, which is not conducive to achieve ambipolar transport.…”

Section: Replacing the Benzene Rings In Isoindigo Unit With Heterocyclesmentioning

confidence: 99%

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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“…Subsequently, they reported a thiophene‐based monomer, bis‐thienobenzo‐IID (bis‐TBI), by coupling two benzothieno‐IID moieties together at the thienyl position and synthesized a copolymer (P46) of bis‐TBI and bithiophene moieties. [ 135 ] The HOMO/LUMO energy level of P46 was −5.43/−4.01 eV. GIXRD results indicated that P46 adopted both edge‐on and face‐on orientations, and the π–π stacking distance was very small (3.51 Å).…”

Section: Improving the Electron Transport Of D–a‐type Sps Via Amsmentioning

confidence: 99%

mentioning

confidence: 99%

Acceptor Modulation Strategies for Improving the Electron Transport in High‐Performance Organic Field‐Effect Transistors

et al. 2021

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High‐performance ambipolar and electronic type semiconducting polymers are essential for fabricating various organic optoelectronic devices and complementary circuits. This review summarizes the strategies of improving the electron transport of semiconducting polymers via acceptor modulation strategies, which include the use of single, dual, triple, multiple, and all acceptors as well as the fusion of multiple identical acceptors to obtain new heterocyclic acceptors. To further improve the electron transport of semiconducting polymers, the introduction of strong electron‐withdrawing groups can enhance the electron‐withdrawing ability of donors and acceptors, thereby facilitating electron injection and suppressing hole accumulation. In addition, the relationships between the molecular structure, frontier molecular orbital energy levels, thin film morphology, microstructure, processing conditions, and device performances are also comprehensively discussed. Finally, the challenges encountered in this research area are proposed and the future outlook is presented.

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Side-Chain Sequence Enabled Regioisomeric Acceptors for Conjugated Polymers

Cited by 15 publications

References 45 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

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

Acceptor Modulation Strategies for Improving the Electron Transport in High‐Performance Organic Field‐Effect Transistors

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