Pyrazine-fused isoindigo: a new building block for polymer solar cells with high open circuit voltage

Li, Jiu-Long; Chai, Yun-Fei; Wang, Wei Vanessa; Shi, Zi‐Fa; Zhang, Xu; Zhang, Hao‐Li

doi:10.1039/c7cc01973d

Cited by 25 publications

(13 citation statements)

References 18 publications

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“…As shown in Figure a, ν(CO) of DR 9 shifts toward lower wavenumbers, while δ(N–H) and ν ar (CC) of DR 9 shift toward higher wavenumbers after DR 9 diffusing into the PET film. It has been previously reported that there are intramolecular hydrogen bonds between the amino group and the carbonyl group of the anthraquinone dye molecule, and the molecular planarity is thus enhanced. − In addition, when the hydrogen bond is formed, ν(CO) and ν(N–H) bands will shift to lower wavenumbers, while the δ(N–H) band is just the opposite, moving to higher wavenumbers. Under such a circumstance, the shift of the bands of ν(CO) and δ(N–H) would indicate the strengthening of intramolecular hydrogen bonds of DR 9 with diffusion, which consequently results in the enhancement of the planarity of the DR 9 molecules and makes it easier for DR 9 molecules to diffuse into the PET film.…”

Section: Resultsmentioning

confidence: 99%

Dynamic Diffusion of Disperse Dye in a Polyethylene Terephthalate Film from an Infrared Spectroscopic Perspective

Liu

Hou

Sun

et al. 2020

Ind. Eng. Chem. Res.

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The diffusion behavior of a typical disperse dye, disperse red 9 (DR 9), in the polyethylene terephthalate (PET) film at different temperatures was investigated by attenuated total reflection–Fourier transform infrared spectroscopy and 2D correlation spectroscopy (2Dcos) analyses. According to the Fickian diffusion model, the calculated diffusion coefficients of DR 9 in the PET film at different temperatures were observed to increase with temperature, which might be attributed to the increased free volume and thermal motion in the PET matrix and the rapid movement of DR 9 molecules at higher temperatures. In-detail analysis of the diffusion spectra discerned various kinds of molecular interactions, that is, intramolecular hydrogen bonding interactions of DR 9 and dipole–dipole and π–π interactions between DR 9 and PET. Among these, the dipole–dipole interactions between CO groups of DR 9 and PET occurred first and played a vital role during the diffusion process of DR 9, as deduced from the sequence order of group motions in 2Dcos analysis.

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Section: Resultsmentioning

confidence: 99%

Dynamic Diffusion of Disperse Dye in a Polyethylene Terephthalate Film from an Infrared Spectroscopic Perspective

Liu

Hou

Sun

et al. 2020

Ind. Eng. Chem. Res.

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“…The polymer P88 contained an acceptor PzIIG, having the 1,4-pyrazine ring as the bridge between two indolinones. 100 The PzIIG had little difference in the HOMO/LUMO energy levels relative to those of the IID counterpart but gave a dense and ordered packing state, whose p-p stacking distance was as small as 3.29Å (Fig. 8b), due to the formed N/H hydrogen bond between 1,4-pyrazine and indolinone.…”

Section: Chemical Science Reviewmentioning

confidence: 98%

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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“…[ 50 ] As shown in Figure 1f, some center‐inserted isoindigo derivatives can be synthesized by the Knoevenagel condensation with oxindole as a precursor. [ 51–53 ] Wan's group synthesized a isoindigo derivative using an oxindole‐based precursor. Inspiringly, the alkylation and condensation are carried out in a one‐pot reaction in this method (Figure 1g).…”

Section: Synthetic Tactics Of Isoindigo‐derived Monomers and Polymersmentioning

confidence: 99%

“…[ 51 ] For P141 , pyrazine was inserted into isoindigo. [ 53 ] In addition to improving the planarity by the intramolecular hydrogen bonding, this fragment also enhanced the electron‐withdrawing ability of the acceptor unit. The fabricated OPVs exhibited a PCE of 5.26% with a V OC higher than 1 V. [ 53 ] Alternatively, Yue and co‐workers synthesized P43 using peripherally extended isoindigo derivative M23 .…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Other Applicationsmentioning

confidence: 99%

“…[ 53 ] In addition to improving the planarity by the intramolecular hydrogen bonding, this fragment also enhanced the electron‐withdrawing ability of the acceptor unit. The fabricated OPVs exhibited a PCE of 5.26% with a V OC higher than 1 V. [ 53 ] Alternatively, Yue and co‐workers synthesized P43 using peripherally extended isoindigo derivative M23 . [ 28 ] P43 possessed high degree of crystallinity, high charge carrier mobility, and homogenous phase separation with PC 71 BM, resulting in a high PCE of 9.1% for as‐cast films.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Other Applicationsmentioning

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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Pyrazine-fused isoindigo: a new building block for polymer solar cells with high open circuit voltage

Cited by 25 publications

References 18 publications

Dynamic Diffusion of Disperse Dye in a Polyethylene Terephthalate Film from an Infrared Spectroscopic Perspective

Dynamic Diffusion of Disperse Dye in a Polyethylene Terephthalate Film from an Infrared Spectroscopic Perspective

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

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

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