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

Zhou, Yankai; Zhang, Weifeng; Yu, Gui

doi:10.1039/d1sc01711j

Cited by 39 publications

(25 citation statements)

References 169 publications

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“…We choose diketopyrropopyrrole (DPP) as the building block because of its good planarity, strong intermolecular interaction, and potentially high charge carrier mobility. [42][43][44][45] Dicyanomethylene-3-ethylrhodanine (RDN) and 3-(dicyanomethylidene)-indan-1-one (IC) are chosen as end functional groups because of their strong electron-withdrawing ability. [46][47][48][49] Particularly, thiophene-fused IC (ThIC) not only has a strong electron-withdrawing ability but could also provide better intermolecular interactions because of its potentially heteroatomic non-covalent interactions.…”

Section: Synthesis and Structure Characterizationmentioning

confidence: 99%

Unveiling the Interplay among End Group, Molecular Packing, Doping Level, and Charge Transport in N‐Doped Small‐Molecule Organic Semiconductors

Wang

et al. 2021

Adv Funct Materials

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Doped small molecules with high electrical conductivity are desired because they typically show a larger Seebeck coefficient and lower thermal conductivity than their polymer counterparts. However, compared with conjugated polymers, only a few small molecules can show high electrical conductivities. In this study, three n-type small-molecule organic semiconductors with different end functional groups are synthesized to explore the reasons for the low electrical conductivity issue in n-doped small-molecule semiconductors. Charge carrier mobility and doping level are usually considered as two major parameters for achieving high electrical conductivity. TDPP-ThIC with high electron mobility of 0.77 cm 2 V −1 s −1 and high electron affinity, which can be easily n-doped; however, it only displays an electrical conductivity ≈10 −3 S cm −1 . To explore the reasons, the single crystal structure of TDPP-ThIC and the grazing incidence wide-angle X-ray scattering of its n-doped films are carefully analyzed. TDPP-ThIC with a 1D column packing is disclosed and easily distorted by the enthetic n-dopants, which damages the charge transport pathways, and thereby results in low electrical conductivity. The results suggests that only high intrinsic charge carrier mobility and high doping level cannot guarantee high electrical conductivity, and keeping good charge transport pathways after doping is also critical.

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Section: Synthesis and Structure Characterizationmentioning

confidence: 99%

Unveiling the Interplay among End Group, Molecular Packing, Doping Level, and Charge Transport in N‐Doped Small‐Molecule Organic Semiconductors

Wang

et al. 2021

Adv Funct Materials

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“…The charge transport layers have a substantial impact on the long-term stability of OSCs. [40][41][42][43][44][45][46][47][48][49][50][51] 1.2 Polymer donors Conjugated compounds that have linked conjugated polymers (p) play a major role in a wide range of products, such as organic light-emitting diodes (OLEDs), thin-lm organic transistors, and dye-sensitized solar cells (DSSCs). The enormous development in the eld of OSCs over the last ve years has drawn signicant attention to this developing technology for the capture of renewable energy.…”

Section: Structure Background and Operation Of Bulk Heterojunction Or...mentioning

confidence: 99%

Fused ring A–DA′D–A (Y-series) non-fullerene acceptors: recent developments and design strategies for organic photovoltaics

Pachaiyappan

et al. 2022

J. Mater. Chem. A

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“…Electron-deficient (n-type) polymers are an important class of organic semiconductors that transport electrons , and are essential components of organic devices such as ambipolar and n-channel field-effect transistors and organic photovoltaics. − Such materials are mostly synthesized using Suzuki or Stille coupling, following a step-growth mechanism with limited control over the polymerization process …”

Section: Homopolymersmentioning

confidence: 99%

Precision Synthesis of Conjugated Polymers Using the Kumada Methodology

2021

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Conspectus Since the discovery of conductive poly(acetylene), the study of conjugated polymers has remained an active and interdisciplinary frontier between polymer chemistry, polymer physics, computation, and device engineering. One of the ultimate goals of polymer science is to reliably synthesize structures, similar to small molecule synthesis. Kumada catalyst-transfer polymerization (KCTP) is a powerful tool for synthesizing conjugated polymers with predictable molecular weights, narrow dispersities, specific end groups, and complex backbone architectures. However, expanding the monomer scope beyond the well-studied 3-alkylthiophenes to include electron-deficient and complex heterocycles has been difficult. Revisiting the successful applications of KCTP can help us gain new insight into the CTP mechanisms and thus inspire breakthroughs in the controlled polymerization of challenging π-conjugated monomers. In this Account, we highlight our efforts over the past decade to achieve controlled synthesis of homopolymers (p-type and n-type), copolymers (diblock and statistical), and monodisperse high oligomers. We first give a brief introduction of the mechanism and state-of-the-art of KCTP. Since the extent of polymerization control is determined by steric and electronic effects of both the catalyst and monomer, the polymerization can be optimized by modifying monomer and catalyst structures, as well as finding a well-matched monomer–catalyst system. We discuss the effects of side-chain steric hindrance and halogens in the context of heavy atom substituted monomers. By moving the side-chain branch point one carbon atom away from the heterocycle to alleviate steric crowding and stabilize the catalyst resting state, we were able to successfully control the polymerization of new tellurophene monomers. Inspired by innocent role of the sterically encumbered 2-transmetalated 3-alkylthiophene monomer, we introduce the treatment of hygroscopic monomers with a bulky Grignard compound as a water-scavenger for the improved synthesis of water-soluble conjugated polymers. For challenging electron-deficient monomers, we discuss the design of new Ni(II)diimine catalysts with electron-donating character which enhance the stability of the association complex between the catalyst and the growing polymer chain, resulting in the quasi-living synthesis of n-type polymers. Beyond n-type homopolymers, the Ni(II)diimine catalysts are also capable of producing electron-rich and electron-deficient diblock and statistical copolymers. We discuss how density functional theory (DFT) calculations elucidate the role of catalyst steric and electronic effects in controlling the synthesis of π-conjugated polymers. Moreover, we demonstrate the synthesis of monodisperse high oligomers by temperature cycling, which takes full advantage of the unique character of KCTP in that it proceeds through distinct intermediates that are not reactive. The insight we gained thus far leads to the first example of isolated living conjugated polymer chains prepar...

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

Abstract: This review highlights the recent structural evolution of lactam- and imide-functionalized polymers applied in organic field-effect transistors and organic solar cells.

Cited by 39 publications

References 169 publications

Unveiling the Interplay among End Group, Molecular Packing, Doping Level, and Charge Transport in N‐Doped Small‐Molecule Organic Semiconductors

Unveiling the Interplay among End Group, Molecular Packing, Doping Level, and Charge Transport in N‐Doped Small‐Molecule Organic Semiconductors

Fused ring A–DA′D–A (Y-series) non-fullerene acceptors: recent developments and design strategies for organic photovoltaics

Precision Synthesis of Conjugated Polymers Using the Kumada Methodology

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