2019
DOI: 10.1002/adfm.201804839
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High‐Performance Ambipolar Polymers Based on Electron‐Withdrawing Group Substituted Bay‐Annulated Indigo

Abstract: For donor-acceptor conjugated polymers, it is an effective strategy to improve their electron mobilities by introducing electron-withdrawing groups (EWGs, such as F, Cl, or CF 3 ) into the polymer backbone. However, the introduction of different EWGs always requires a different synthetic approach, leading to additional arduous work. Here, an effective two-step method is developed to obtain EWG substituted bay-annulated indigo (BAI) units. This method is effective to introduce various EWGs (F, Cl, or CF 3 ) int… Show more

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Cited by 32 publications
(29 citation statements)
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“…Polymer materials with advantages of superior viscosity, thermal, mechanical and simple processing characteristics have been proverbially employed in photovoltaics (PV), transistors, light‐emitting diodes, logic circuits, sensors, etc . Particularly, D–A polymers that possess noncovalent intramolecular interactions for efficient π‐conjugation and close stacking ensuring intermolecular charge hopping have been extensively investigated . The conjugated polymers consisting of donors including selenophenes and thiophenes and acceptors comprising DPPs, NDIs, isoindigos, thiadiazolopyridine, naphthalenedicarboximide, and benzothiadiazole are mainly synthesized via Stille, Suzuki, and direct arylation polycondensation.…”
Section: Ambipolar Organic Semiconducting Materialsmentioning
confidence: 99%
“…Polymer materials with advantages of superior viscosity, thermal, mechanical and simple processing characteristics have been proverbially employed in photovoltaics (PV), transistors, light‐emitting diodes, logic circuits, sensors, etc . Particularly, D–A polymers that possess noncovalent intramolecular interactions for efficient π‐conjugation and close stacking ensuring intermolecular charge hopping have been extensively investigated . The conjugated polymers consisting of donors including selenophenes and thiophenes and acceptors comprising DPPs, NDIs, isoindigos, thiadiazolopyridine, naphthalenedicarboximide, and benzothiadiazole are mainly synthesized via Stille, Suzuki, and direct arylation polycondensation.…”
Section: Ambipolar Organic Semiconducting Materialsmentioning
confidence: 99%
“…Liu et al developed a two-step method to obtain a series of copolymers (P29a−P29c) based on BAI with different substituents (H, F, and Cl). [83] Fluorination and chlorination of the polymers effectively lowered both the HOMO and LUMO energy levels compared with P29a. P29b and P29c showed low-lying HOMO/LUMO energy levels of −5.58/−3.72 and −5.32/−3.70 eV, respectively.…”
Section: Enhancing the Ew Ability Of Acceptorsmentioning
confidence: 97%
“…[80,81] 2) Similar to F substitution, chlorine (Cl) substitution can lower the FMO energy levels of polymers. [82,83] However, Cl atoms might cause steric hindrance in the molecule due to a large van der Waals radius (r Cl = 1.80 Å), which is harmful to π-conjugate and intermolecular π-π stacking. [15] 3) In addition to the F and Cl atoms, CN group is also a strong EWG that can significantly lower the FMO energy levels of polymers.…”
Section: Design Strategies For Improving Electron Transport In Ofetsmentioning
confidence: 99%
“…Based on bay-annulated indigo (BAI) compounds, Yang et al introduced electron-withdrawing groups (F and Cl) to the backbone and obtained P4 to P6 (shown in Figure ). The FMO energy levels were lowered after F and Cl substitution and the HOMO/LUMO energy levels of P4 to P6 were −5.22/–3.65, – 5.58/–3.72, and–5.32/–3.70 eV, respectively. Because of the electronegativity and empty 3d orbitals of the Cl atom, the LUMO energy level was lowered and the π-electrons from donors could be accepted after Cl substitution.…”
Section: Molecular Design Of High-performance Semiconducting Polymersmentioning
confidence: 99%