Linear-type carbazoledioxazine-based organic semiconductors: the effect of backbone planarity on the molecular orientation and charge transport properties

Otsuka, Rikuo; Wang, Yang; Mori, Takehiko; Michinobu, Tsuyoshi

doi:10.1039/c8ra01088a

Cited by 7 publications

(4 citation statements)

References 63 publications

(101 reference statements)

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“…The overlap of π‐orbits of conjugated cores can efficiently facilitate the assembly of adjacent molecules. [ 112 ] In addition to the size effect, the intrinsic properties of the conjugated backbone can be adjusted by including heteroatoms or functional groups. [ 113 ] The alteration of the electronegativity and distribution of electron clouds can further affect the aggregation of OSs, which can significantly diversify the morphology and properties of multiscale OS materials.…”

Section: Basic Design Principle For Multiscale Ossmentioning

confidence: 99%

Controlled Growth and Self‐Assembly of Multiscale Organic Semiconductor

Bai

Wang

2021

Advanced Materials

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Currently, organic semiconductors (OSs) are widely used as active components in practical devices related to energy storage and conversion, optoelectronics, catalysis, and biological sensors, etc. To satisfy the actual requirements of different types of devices, chemical structure design and self‐assembly process control have been synergistically performed. The morphology and other basic properties of multiscale OS components are governed on a broad scale from nanometers to macroscopic micrometers. Herein, the up‐to‐date design strategies for fabricating multiscale OSs are comprehensively reviewed. Related representative works are introduced, applications in practical devices are discussed, and future research directions are presented. Design strategies combining the advances in organic synthetic chemistry and supramolecular assembly technology perform an integral role in the development of a new generation of multiscale OSs.

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Section: Basic Design Principle For Multiscale Ossmentioning

confidence: 99%

Controlled Growth and Self‐Assembly of Multiscale Organic Semiconductor

Bai

Wang

2021

Advanced Materials

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“…A few years later this series of copolymers outperformed polycrystalline Si (>10 cm 2 V –1 s –1 ) upon processing improvements and broke the record among the conjugated polymers at that time . In addition to DPP, ,,− naphthalenediimide (NDI), − isoindigo (IID), , benzobis[1,2,5]thiadiazole (BBT), − and other dye and pigment building blocks − have been studied and proven to deliver polymers with superior field-effect mobilities. Despite its “strong” electron-accepting character, BBT was less studied than the others, mainly due to the low solubility.…”

Section: Introductionmentioning

confidence: 96%

Tuning Backbone Planarity in Thiadiazolobenzotriazole–Bis(thienothiophenyl)ethylene Copolymers for Organic Field-Effect Transistors

Otep

Wang

Kohara

et al. 2019

ACS Appl. Polym. Mater.

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Thiadiazolo[3,benzotriazole (TBZ) and bis(thieno[3,2-b]thiophenyl)ethylene (DTTE)-based conjugated polymers were designed and synthesized by Stille polycondensation, and the effect of the side chain alkyl positions on the optical, electrochemical, and charge-transporting properties in organic field-effect transistors was comprehensively studied. By optimizing the alkyl positions, we obtained semicrystalline polymers, but their hole mobilities were ∼0.1 cm 2 V −1 s −1 due to the face-on dominant orientation. It was also found that the thiophene spacers, which have traditionally been present in the TBZ-based copolymers, are the source of the backbone torsion. Removal of the thiophene units produced an almost planar copolymer backbone with an edge-on and bimodal texture, which exhibited the improved hole mobility exceeding 0.4 cm 2 V −1 s −1 .

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“…Similar structure was also reported in OFET devices recently. [ 47 ] To develop the benzimidazolone‐dioxazine‐based pigment as active semiconductive materials on OFET devices, in this study, we designed six novel benzimidazolone‐dioxazine‐based D–A conjugated polymers ( Scheme ), with one to six thiophenes (P1–P6) as donors to investigate the benzimidazolone‐dioxazine as acceptor units in conjugated polymers. Most synthesized polymers (P2–P6) exhibited high molecular weight, which are essential for high‐performance OFET.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazolone‐Dioxazine Pigments‐Based Conjugated Polymers for Organic Field‐Effect Transistor

Tung

Cheng

Huang

et al. 2022

Macromol. Rapid Commun.

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Molecules based on benzimidazolone‐dioxazine are known as blue/violet pigments and have been commercialized for decades. However, unfavorable solubility limits the application of these structures as building blocks of conjugated polymers despite their low band gaps. Herein, a series of donor–acceptor conjugated polymers containing soluble benzimidazolone‐dioxazine structures as the acceptors and oligothiophene as donors are synthesized and investigated. With increasing numbers of thiophene rings, the steric hindrance diminishes and high molecular weight polymers can be achieved, leading to an improved performance in organic field effect transistor devices. The hole mobility of polymers with three to six thiophene units is in the order of 10−1 cm2 V−1 s −1. Among all the polymers, polymer P3 with three thiophene units between benzimidazolone‐dioxazine structures shows the best hole mobility of 0.4 cm2 V−1 s −1. Grazing‐incidence wide‐angle X‐ray scattering results reveal that the high mobility of organic field‐effect transistors (OFETs) can be accredited by matched donor–acceptor packing in the solid thin films.

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Linear-type carbazoledioxazine-based organic semiconductors: the effect of backbone planarity on the molecular orientation and charge transport properties

Abstract: A linear-type dibromocarbazoledioxazine (CZ) derivative and its two polymers are newly designed and synthesized. Structure–property relationship studies reveal that PCZTT shows a four times higher hole mobility than PCZT.

Cited by 7 publications

References 63 publications

Controlled Growth and Self‐Assembly of Multiscale Organic Semiconductor

Controlled Growth and Self‐Assembly of Multiscale Organic Semiconductor

Tuning Backbone Planarity in Thiadiazolobenzotriazole–Bis(thienothiophenyl)ethylene Copolymers for Organic Field-Effect Transistors

Benzimidazolone‐Dioxazine Pigments‐Based Conjugated Polymers for Organic Field‐Effect Transistor

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