Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

π-Conjugated organic donor–acceptor (D–A) type polymers are widely developed and used in electronic device. Among which, diketopyrrolopyrrole (DPP)-based polymers have received the most attention due to their high performances. The novel chromophores named 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), benzodipyrrolidone (BDP) and naphthodipyrrolidone (NDP) are resemble DPP in chemical structure. IsoDPP is an isomer of DPP, with the switching position of carbonyl and amide units. The cores of BDP and NDP are tri- and tetracyclic, whereas isoDPP is bicyclic. π-Conjugation extension could result polymers with distinct optical, electrochemical and device performance. It is expected that the polymers containing these high-performance electron-deficient pigments are potential in the electronic device applications, and have the potential to be better than the DPP-based ones. IsoDPP, BDP, and NDP based polymers are synthesized since 2011, and have not receive desirable attention. In this work, the synthesis, properties (optical and electrochemical characteristics), electronic device as well as their relationship depending on core-extension or structure subtle optimization have been reviewed. The final goal is to outline a theoretical scaffold for the design the D–A type conjugated polymers, which is potential for high-performance electronic devices.

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Synthesis of the novel thienoisoindigo-based donor-acceptor type conjugated polymers and the stable switching performance of purple-to-transparent as the electrochromic materials

Organic Electronics ◽

10.1016/j.orgel.2021.106183 ◽

2021 ◽

pp. 106183

Author(s):

Haoguo Yue ◽

Xiuping Ju ◽

Yuchang Du ◽

Yan Zhang ◽

Hongmei Du ◽

...

Keyword(s):

Conjugated Polymers ◽

The Novel ◽

Electrochromic Materials ◽

Switching Performance ◽

Donor Acceptor

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Structure Design for High Performance n-Type Polymer Thermoelectric Materials

Chinese Physics B ◽

10.1088/1674-1056/ac3a64 ◽

2021 ◽

Author(s):

Qi Zhang ◽

Hengda Sun ◽

Meifang Zhu

Keyword(s):

Conjugated Polymers ◽

Thermoelectric Materials ◽

High Performance ◽

Waste Heat ◽

Building Blocks ◽

Structure Design ◽

Potential Candidate ◽

Polymer Backbone ◽

P Type ◽

Polymer Thermoelectric

Abstract Organic thermoelectric (OTE) materials have been regarded as a potential candidate to harvest waste heat from complex, low temperature surfaces of objects and convert it into electricity. Recently, n-type conjugated polymers as organic thermoelectric materials have aroused intensive research in order to improve their performance to match up with their p-type counterpart. In this review, we discuss aspects that affect the performance of n-type OTEs, and further focus on the effect of planarity of backbone on doping efficiency and eventually the TE performance. We then summarize strategies such as implementing rigid n-type polymer backbone or modifying conventional polymer building blocks for more planar conformation. In the outlook part, we conclude forementioned devotions and point out new possibility that may promote the future development of this field.

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Regioregularity-Control of Conjugated Polymers: From Synthesis, Properties, to Photovoltaic Device Applications

Journal of Materials Chemistry A ◽

10.1039/d1ta08495j ◽

2022 ◽

Author(s):

Youngkwon Kim ◽

Hyeonjung Park ◽

Jin Su Park ◽

Jin-Woo Lee ◽

Hyeong Jun Kim ◽

...

Keyword(s):

Conjugated Polymers ◽

Organic Electronics ◽

Photovoltaic Device ◽

Molecular Structures ◽

Synthesis Properties ◽

Device Applications ◽

The Relationship

In the last decade, extensive academic and industrial efforts have been devoted to developing efficient conjugated polymers (CPs) for organic electronics. Specifically, the relationship between the molecular structures, properties, and...

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High-performance, semiconducting membrane composed of ultrathin, single-crystal organic semiconductors

Proceedings of the National Academy of Sciences ◽

10.1073/pnas.1909932116 ◽

2019 ◽

Vol 117 (1) ◽

pp. 80-85 ◽

Cited By ~ 5

Author(s):

Tatsuyuki Makita ◽

Shohei Kumagai ◽

Akihito Kumamoto ◽

Masato Mitani ◽

Junto Tsurumi ◽

...

Keyword(s):

Single Crystal ◽

Organic Semiconductors ◽

High Performance ◽

Printed Electronics ◽

Electronic Device ◽

Molecular Layer ◽

High Mobility ◽

Building Blocks ◽

Solution Processed ◽

Transfer Method

Thin film transistors (TFTs) are indispensable building blocks in any electronic device and play vital roles in switching, processing, and transmitting electronic information. TFT fabrication processes inherently require the sequential deposition of metal, semiconductor, and dielectric layers and so on, which makes it difficult to achieve reliable production of highly integrated devices. The integration issues are more apparent in organic TFTs (OTFTs), particularly for solution-processed organic semiconductors due to limits on which underlayers are compatible with the printing technologies. We demonstrate a ground-breaking methodology to integrate an active, semiconducting layer of OTFTs. In this method, a solution-processed, semiconducting membrane composed of few-molecular-layer–thick single-crystal organic semiconductors is exfoliated by water as a self-standing ultrathin membrane on the water surface and then transferred directly to any given underlayer. The ultrathin, semiconducting membrane preserves its original single crystallinity, resulting in excellent electronic properties with a high mobility up to 12cm2⋅V−1⋅s−1. The ability to achieve transfer of wafer-scale single crystals with almost no deterioration of electrical properties means the present method is scalable. The demonstrations in this study show that the present transfer method can revolutionize printed electronics and constitute a key step forward in TFT fabrication processes.

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π-Conjugation expanded isoindigo derivatives and the donor–acceptor conjugated polymers: synthesis and characterization

Chemical Communications ◽

10.1039/c7cc08603b ◽

2018 ◽

Vol 54 (7) ◽

pp. 782-785 ◽

Cited By ~ 10

Author(s):

Hao Song ◽

Yunfeng Deng ◽

Yu Jiang ◽

Hongkun Tian ◽

Yanhou Geng

Keyword(s):

Conjugated Polymers ◽

Building Blocks ◽

Synthesis And Characterization ◽

Donor Acceptor

π-Conjugation expanded isoindigo derivatives were synthesized via intramolecular Friedel–Crafts acylation, which are promising building blocks for ambipolar conjugated polymers.

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Constructing Donor-Resonance-Donor Molecules for Acceptor-Free Bipolar Organic Semiconductors

Research ◽

10.34133/2021/9525802 ◽

2021 ◽

Vol 2021 ◽

pp. 1-10

Author(s):

He Jiang ◽

Jibiao Jin ◽

Zijie Wang ◽

Wuji Wang ◽

Runfeng Chen ◽

...

Keyword(s):

Organic Semiconductors ◽

High Performance ◽

Molecular Design ◽

Stimuli Responsive ◽

Light Emitting ◽

Deep Blue ◽

Device Structures ◽

Device Applications ◽

Donor Acceptor ◽

Organic Optoelectronic

Organic semiconductors with bipolar transporting character are highly attractive as they offer the possibility to achieve high optoelectronic performance in simple device structures. However, the continual efforts in preparing bipolar materials are focusing on donor-acceptor (D-A) architectures by introducing both electron-donating and electron-withdrawing units into one molecule in static molecular design principles. Here, we report a dynamic approach to construct bipolar materials using only electron-donating carbazoles connected by N-P=X resonance linkages in a donor-resonance-donor (D-r-D) structure. By facilitating the stimuli-responsive resonance variation, these D-r-D molecules exhibit extraordinary bipolar properties by positively charging one donor of carbazole in enantiotropic N+=P-X- canonical forms for electron transport without the involvement of any acceptors. With thus realized efficient and balanced charge transport, blue and deep-blue phosphorescent organic light emitting diodes hosted by these D-r-D molecules show high external quantum efficiencies up to 16.2% and 18.3% in vacuum-deposited and spin-coated devices, respectively. These results via the D-r-D molecular design strategy represent an important concept advance in constructing bipolar organic optoelectronic semiconductors dynamically for high-performance device applications.

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Effects of the Electron-Deficient Third Components in n-Type Terpolymers on Morphology and Performance of All-Polymer Solar Cells

Organic Materials ◽

10.1055/s-0040-1713857 ◽

2020 ◽

Vol 02 (03) ◽

pp. 214-222

Author(s):

Bin Liu ◽

Huiliang Sun ◽

Chang Woo Koh ◽

Mengyao Su ◽

Bao Tu ◽

...

Keyword(s):

Solar Cells ◽

High Performance ◽

Noncovalent Interactions ◽

Polymer Solar Cells ◽

Energy Levels ◽

Building Blocks ◽

The Third ◽

Donor Acceptor ◽

And Performance ◽

P Type

Compared with p-type terpolymers, less effort has been devoted to n-type analogs. Herein, we synthesized a series of n-type terpolymers via incorporating three electron-deficient third components including thienopyrroledione (TPD), phthalimide, and benzothiadiazole into an imide-functionalized parent n-type copolymer to tune optoelectronic properties without sacrificing the n-type characteristics. Due to effects of the third components with different electron-accepting ability and solubility, the resulting three polymers feature distinct energy levels and crystallinity. In addition, heteroatoms (S, O, and N) attached on the third components trigger intramolecular noncovalent interactions, which can increase molecule planarity and have a significant effect on the packing structures of the polymer films. As a result, the best power conversion efficiency of 8.28% was achieved from all-polymer solar cells (all-PSCs) based on n-type terpolymer containing TPD. This is contributed by promoted electron mobility and face-on polymer packing, showing the pronounced advantages of the TPD used as a third component for thriving efficient n-type terpolymers. The generality is also successfully validated in a benchmark polymer donor/acceptor system by introducing TPD into the benchmark n-type polymer N2200. The results demonstrate the feasibility of introducing suitable electron-deficient building blocks as the third components for high-performance n-type terpolymers toward efficient all-PSCs.

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Donor–acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells

Chemical Society Reviews ◽

10.1039/c4cs00250d ◽

2015 ◽

Vol 44 (5) ◽

pp. 1113-1154 ◽

Cited By ~ 414

Author(s):

Jhong-Sian Wu ◽

Sheng-Wen Cheng ◽

Yen-Ju Cheng ◽

Chain-Shu Hsu

Keyword(s):

Solar Cells ◽

Conjugated Polymers ◽

Organic Solar Cells ◽

Building Blocks ◽

Donor Acceptor ◽

Conjugated Copolymers

In this review, we summarize the recent development of the multifused ladder-type conjugated building blocks for making donor–acceptor conjugated copolymers.

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Lactone-fused electron-deficient building blocks for n-type polymer field-effect transistors: synthesis, properties, and impact of alkyl substitution positions

Polymer Chemistry ◽

10.1039/c6py00143b ◽

2016 ◽

Vol 7 (12) ◽

pp. 2264-2271 ◽

Cited By ~ 5

Author(s):

Xiao-Ye Wang ◽

Meng-Wen Zhang ◽

Fang-Dong Zhuang ◽

Jie-Yu Wang ◽

Jian Pei

Keyword(s):

Conjugated Polymers ◽

Field Effect ◽

Field Effect Transistors ◽

Building Blocks ◽

Design Concept ◽

Polymer Semiconductors ◽

Alkyl Substitution ◽

Synthesis Properties

Dilactone-based Pechmann dyes were incorporated into conjugated polymers for n-type field-effect transistors, providing a new design concept of electron-deficient building blocks for polymer semiconductors.

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