Modulating charge transport characteristics of bis-azaisoindigo-based D–A conjugated polymers through energy level regulation and side chain optimization

Huang, Kaiqiang; Zhao, Xiangyu; Du, Yuchang; Kim, Sang-Hyo; Wang, Xiaohong; Lu, Hongbo; Cho, Kilwon; Zhang, Guobing; Qiu, Longzhen

doi:10.1039/c9tc02021g

Cited by 28 publications

(33 citation statements)

References 55 publications

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“…With the success of M5 ‐based polymers, thereafter, several isoindigo derivatives with similar design concepts were reported. [ 23,102–107 ] Two main strategies were followed: i) replacing the lactones with lactams or thioesters, and ii) extending conjugation of the inserted benzodifurandione fragment via replacing the phenyl ring with larger aromatic ring (Figure 5b). Replacing the phenyl ring with naphthalene, Li and co‐workers synthesized M6 .…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

“…P29 based on aza‐ M8 exhibited higher both hole and electron mobilities than those of M8 ‐based polymers. [ 106 ] Moreover, Li’ group replaced the O atoms in lactams with S atoms to produce M10 . [ 107 ] M10 ‐based P30 showed suitable energy levels for ambipolar transport but large π–π stacking distance.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

“…[ 138 ] Similar to fluorinated bithiophene, fluorinated DTE has also been used to achieve electron transport. [ 30,106 ] Besides fluorinate atom, other substituent groups such as cyano groups (CN) were used to lower polymers energy levels and approach electron transport. [ 139,140 ] Selenophene‐containing conjugated polymers have been shown to effectively improve intermolecular interaction and facilitate charge transport due to the larger orbital of selenium.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

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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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Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

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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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“…[8][9][10] Thirdly, a variety of side chains can be substituted on the amide nitrogen atom to adjust the polymer solubility, lm morphology, and the selfassembly of the side chain. [11][12][13] Some functional side chains were also incorporated into polymers to fabricate devices with a specic function. [14][15][16] In recent years, numerous lactam-and imide-functionalized polymers with high carrier mobilities have been reported.…”

Section: Introductionmentioning

confidence: 99%

Recent structural evolution of lactam- and imide-functionalized polymers applied in organic field-effect transistors and organic solar cells

Zhou

Zhang

2021

Chem. Sci.

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“…[ 11–14 ] In addition, embedding sp 2 ‐nitrogen onto a conjugated backbone and increasing conjugation length are also possible ways to tune the frontier molecular orbitals (FMOs) for better air stability. [ 15–18 ]…”

Section: Introductionmentioning

confidence: 99%

Enhancement of air stability and photovoltaic performance in organic solar cells by structural modulation of bis‐amide‐based donor‐acceptor copolymers: A computational insight

Bhattacharya

Sharma

Sahu

2020

Int J of Quantum Chemistry

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The effect of structural modulation on a series of donor‐acceptor (D‐A) copolymers (1‐7), comprising of thieno[3,2‐b]thiophene (TT) donor and thiazole‐flanked different bis‐amide‐functionalized acceptor units, has been explored. Structural functionalization has been performed by incorporating aromatic rings in the bis‐amide‐functionalized bipyrrolylidene‐2,2′(1H,1′H)‐dione (BPD) (1) acceptor unit, and six D‐A copolymers containing isoindigo (2), azaisoindigo (3), benzoisoindigo (4), benzoazaisoindigo (5), 1,5‐naphthyridine‐BPD (6), and 1,8‐naphthyridine‐BPD (7) as acceptor units are designed. Density functional theory has been employed to understand the impact of structural modulation on geometrical, optoelectronic, charge transport, and photovoltaic properties of the copolymers. The higher proportion of N‐heteroatom in copolymers 3, 6, and 7 leads to low‐lying highest occupied molecular orbital (lowest unoccupied molecular orbital) levels and thus improves their air stability and open‐circuit voltage. The computed optical absorption in the visible range (602‐754 nm) ensures that the studied compounds can efficiently harvest photon energy. The ratio of charge transfer rate (KCT) and charge recombination rate (KCR) at donor/PC61BM interfaces of structurally tuned copolymers are found to be ∼107 to 1022 times higher than 1/PC61BM. The maximum predicted power conversion efficiency by Scharber diagram could reach up to ∼8% for 3, 6, and 7. The calculated results shed light on the fact that the structural modulation of bis‐amide‐functionalized D‐A copolymers can efficaciously lead to enhanced air stability and photovoltaic performance.

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Modulating charge transport characteristics of bis-azaisoindigo-based D–A conjugated polymers through energy level regulation and side chain optimization

Abstract: Six donor–acceptor (D–A) conjugated polymers, P1–P6, based on the novel electron acceptors bis-isoindigo (BIID) and bis-azaisoindigo (BAID), were designed and synthesized for solution-processed organic field-effect transistors.

Cited by 28 publications

References 55 publications

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

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

Recent structural evolution of lactam- and imide-functionalized polymers applied in organic field-effect transistors and organic solar cells

Enhancement of air stability and photovoltaic performance in organic solar cells by structural modulation of bis‐amide‐based donor‐acceptor copolymers: A computational insight

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