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Alkoxy-Functionalized Bithiophene/thiazoles: Versatile Building Blocks for High-Performance Organic and Polymeric Semiconductors

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Accounts of Materials Research 2023年第3期4卷 237-250页

作者： Kun Yang Zhicai Chen Yimei Wang Xugang Guo Department of Materials Science and Engineering Southern University of Science and Technology(SUSTech)ShenzhenGuangdong 518055China State Key Laboratory of Chemo/Biosensing and Chemometrics College of Chemistry and Chemical EngineeringHunan UniversityChangshaHunan 410082China

CONSPECTUS:Organic electronics has experienced substantial advances in the past decade,driven by the development of high-performance organic semiconductors(OSCs)in combination with device engineering.While the pursuit of new aromatic building blocks has been a central topic in OSC innovation,the installation of novel side chains is also of significance for accessing high-performance solution-processable OSCs due to their great impact on(macro)molecular conformation/configuration,energy levels,intra/intermolecular interaction,and packing motifs,as well as film morphology of the materials.Compared to tuning the length,branching point,anchoring position,and terminal group of alkyl side chains,alkoxy functionalization can afford multifaceted advantages by modulating the properties of bothπ-conjugated main chains and side chain substituents.For instance,the oxygen atom in alkoxy chains not only greatly decreases the steric hindrance between adjacent aromatic rings due to its reduced van der Waal radius(∼1.4Å)versus that of a CH_(2) moiety(∼2.0Å)but also induces intramolecular noncovalent interaction for improving backbone coplanarity and charge transport properties.The highly electron-donating alkoxy chains can also greatly facilitate the intramolecular charge transfer(ICT),and hence the resulting semiconductors can yield absorption beyond the infrared region,which is essential for full coverage of solar absorption in photovoltaic devices.Additionally,the high polarity of oligo(ethylene glycol)-type alkoxy side chains can improve the miscibility of the OSCs with molecular dopants and ions,thus enabling them as a key part of the OSCs for emerging applications such as organic thermoelectrics and organic electrochemical transistors.In this Account,we summarize our pioneering and systematic efforts on the rational design,synthesis,and applications of novel alkoxy-functionalized head-to-head(HH)-linked bithiophene/thiazole-based building blocks and related organic/polymeric semiconductors.First,starting with a brief retros

关键词： properties chains hence

26 mA cm-2 JSC achieved in the integrated solar cells

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Science Bulletin 2019年第23期64卷 1747-1749页

作者： Qiaogan Liao Huiliang Sun Bolin Li Xugang Guo Department of Materials Science and Engineering Southern University of Science and Technology

Organometal halide perovskite has drawn much attention due to their high light-absorption coefficient,outstanding carrier mobility,and long-range charge-transport lengths.The most remarkable progress made by this type of perovskite materials is in the field of photovoltaics[1–4].The power conversion efficiency(PCE)of perovskite solar cells(PSCs)has exceeded 25%since they were first used as the active layer in solar cells in 2009[5].

关键词： perovskite halide absorption

PY-IT,an Excellent Polymer Acceptor

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Chinese Journal of Chemistry 2023年第24期41卷 3714-3728页

作者： Qingqing Bai Qiming Liang Qian Liu Bin Liu Xugang Guo Li Niu Huiliang Sun Center for Advanced Analytical Science Guangzhou Key Laboratory of Sensing Materials and DevicesGuangdong Engineering Technology Research Center for Photoelectric Sensing Materials and DevicesSchool of Chemistry and Chemical EngineeringGuangzhou UniversityGuangzhouGuangdong510006 China Department of Materials Science and Engineering Southern University of Science and Technology (SUSTech)ShenzhenGuangdong518055 China

All-polymer solar cells(all-PSCs)have attracted considerable attention due to their inherent advantages over other types of organic solar cells,including superior optical and thermal stability,as well as exceptional mechanical durability.Recently,all-PSCs have experienced remarkable advancements in device performance thanks to the invention of polymerized small-molecule acceptors(PSMAs)since 2017.Among these PSMAs,PY-IT has garnered immense interest from the scientific community due to its exceptional performance in all-PSCs.In this review,we presented the design principles of PY-IT and discussed the various strategies employed in device engineering for PY-IT-based all-PSCs.These strategies include additive and interface engineering,layer-by-layer processing methods,meniscus-assisted coating methods,and ternary strategy.Furthermore,this review highlighted several novel polymeric donor materials that are paired with PY-IT to achieve efficient all-PSCs.Lastly,we summarized the inspiring strategies for further advancing all-PSCs based on PY-IT.These strategies aim to enhance the overall performance and stability of all-PSCs by exploring new materials,optimizing device architectures,and improving fabrication techniques.By leveraging these approaches,we anticipate significant progress in the development of all-PSCs and their potential as a viable renewable energy source.

关键词： PY-IT Polymer acceptors Device engineering Organic solar cells Synthesis design

采用潮流控制器的贯通型牵引供电系统负序治理模型及控制策略

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中国铁道科学 2024年第1期45卷 155-161页

作者：郭旭刚中国铁道科学研究院集团有限公司机车车辆研究所北京100081

针对树形双边贯通牵引供电系统负序导致的电力系统侧公共连接点处三相电压不平衡问题,提出在树形双边贯通牵引供电系统中加装由降压变压器、潮流控制器(PFC)和控制器组成的补偿装置进行功率转移的负序补偿方案;在建立采用PFC的贯通型牵... 详细信息

针对树形双边贯通牵引供电系统负序导致的电力系统侧公共连接点处三相电压不平衡问题,提出在树形双边贯通牵引供电系统中加装由降压变压器、潮流控制器(PFC)和控制器组成的补偿装置进行功率转移的负序补偿方案;在建立采用PFC的贯通型牵引供电系统拓扑结构和数学模型的基础上,设计合理的约束参数和控制策略,通过控制补偿装置改变电力系统侧功率分布,从而实现负序补偿;采用MATLAB/Simulink仿真试验平台,分析补偿装置所需容量随负序补偿程度的变化规律,并计算最小化负序补偿容量,对补偿方案进行验证。结果表明:基于功率转移的负序补偿方案能够灵活调节公共连接点处负序功率和无功功率含量;可将公共连接点处三相电压不平衡度的最大值降低至4%,95%统计值降低至2%,满足了国家标准,从而验证了基于功率转移负序补偿方案的有效性。

关键词：牵引供电系统贯通供电负序补偿无功补偿潮流控制器

Regioisomeric Polymer Semiconductors Based on Cyano-Functionalized Dialkoxybithiophenes:Structure-Property Relationship and Photovoltaic Performance

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Transactions of Tianjin University 2022年第5期28卷 385-397页

作者： Qingqing Bai Jun Huang Han guo Suxiang Ma Jie Yang Bin Liu Kun Yang Huiliang Sun Han Young Woo Li Niu Xugang Guo Center for Advanced Analytical Science School of Chemistry and Chemical EngineeringGuangzhou UniversityGuangzhou 510006China Department of Materials Science and Engineering Southern University of Science and TechnologyShenzhen 518055China State Key Laboratory of Luminescent Materials and Devices South China University of TechnologyGuangdong 510640China Department of Chemistry Korea UniversitySeoul 136-713South Korea

Cyano substitution is vital to the molecular design of polymer semiconductors toward highly efficient organic solar cells.However,how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly understood.Three regioisomeric cyano-functionalized dialkoxybithiophenes BT_(HH),BT_(HT),and BT_(TT) with headto-head,head-to-tail,and tail-to-tail linkage,respectively,were synthesized and characterized in this work.The resulting polymer semiconductors(PBDTBTs)based on these building blocks were prepared accordingly.The regiochemistry and property relationships of PBDTBTs were investigated in detail.The BTHH moiety has a higher torsional barrier than the analogs BT_(HT) and BT_(TT),and the regiochemistry of dialkoxybithiophenes leads to fine modulation in the optoelectronic properties of these polymers,such as optical absorption,band gap,and energy levels of frontier molecular orbitals.Organic field-effect transistors based on PBDTBT_(HH) had higher hole mobility(4.4×10^(-3) cm^(2)/(V·s))than those(ca.10^(-4) cm^(2)/(V·s))of the other two polymer analogs.Significantly different short-circuit current densities and fill factors were obtained in polymer solar cells using PBDTBTs as the electron donors.Such difference was probed in greater detail by performing space-charge-limited current mobility,thin-film morphology,and transient photocurrent/photovoltage characterizations.The findings highlight that the BTHH unit is a promising building block for the construction of polymer donors for highperformance organic photovoltaic cells.

关键词： Cyano substitution Regioselectivity Organic photovoltaic cells Polymer semiconductors Mobility

A Cost-Effective D-A-D Type Hole-Transport Material Enabling 20% Efficiency Inverted Perovskite Solar Celis

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Chinese Journal of Chemistry 2021年第6期39卷 1545-1552页

作者： Jiachen Huang Jie Yang Huiliang Sun Kui Feng Qiaogan Liao Bolin Li He Yan Xugang Guo Department of Materials Science and Engineering Southern University of Science and Technology(SUSTech)No.1088Xueyuan RoodShenzhenGuangdong 518055China Depanment of Chemistry The Hong Kong University of Science and TechnologyClear Water BayHong KongChina School of Materials Science and Engineering Harbin Institute of TechnologyHorbinHeilongjiang 150001China

High-performance,cost-effective hole-transport materials(HTMs)are greatly desired for the commercialization of perovskite solar cells(PVSCs).Herein,two new HTMs,TPA-FO and TPA-PDO,are devised and synthesized,which have a donor-acceptor-donor(D-A-D)type molecule design featuring carbonyl group-functionalized arenes as the acceptor(A)units.The carbonyl group at the central core of HTMs can not only tune frontier molecular orbital(FMO)energy levels and surface wettability,but also can enable efficient surface passivation effects,resulting in reduced recombination loss.When employed as HTMs in inverted PVSCs without using dopant,TPA-FO with one carbonyl group yields a high power conversion efficiency(PCE)of 20.24%,which is among the highest values reported in the inverted PVSCs with dopant-free HTMs.More importantly,the facile one-step synthetic process enables a low cost of 30 USD g^(-1) for TPA-FO,much cheaper than the most studied HTMs used for high-efficiency dopant-free PVSCs.These results demonstrate the potential of D-A-D type molecules with carbonyl group-functionalized arene core in developing the low-cost dopant-free HTMs toward highly efficient PVSCs.

关键词： Energy conversion Donor-acceptor systems Interfaces Hole-transport materials Inverted perovskite solar cells

Self-assembled donor-acceptor hole contacts for inverted perovskite solar cells with an efficiency approaching 22%: The impact of anchoring groups

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Journal of Energy Chemistry 2022年第5期31卷 87-95页

作者： Qiaogan Liao Yang Wang Zilong Zhang Kun Yang Yongqiang Shi Kui Feng Bolin Li Jiachen Huang Peng Gao Xugang Guo Department of Materials Science and Engineering Guangdong Provincial Key Laboratory of Functional Oxide Materials and DevicesSouthern University of Science and Technology(SUSTech)Shenzhen 518055GuangdongChina College of Materials Fujian Key Laboratory of Advanced MaterialsXiamen UniversityXiamen 361005FujianChina CAS Key Laboratory of Design and Assembly of Functional Nanostructures Fujian Provincial Key Laboratory of NanomaterialsFujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhou 350002FujianChina School of Materials Science and Engineering Harbin Institute of TechnologyHarbin 150001HeilongjiangChina

Self-assembled molecules(SAMs) have shown great potential in replacing bulk charge selective contact layers in high-performance perovskite solar cells(PSCs) due to their low material consumption and simple processing. Herein, we design and synthesize a series of donor-acceptor(D-A) type SAMs(MPA-BTCA, MPA-BT-BA, and MPA-BT-RA, where MPA is 4-methoxy-N-(4-methoxyphenyl)-N-phenylaniline;BT is benzo[c][1,2,5]-thiadiazole;CA is 2-cyanoacrylic acid, BA is benzoic acid, RA is rhodanine-3-propionic acid) with distinct anchoring groups, which show dramatically different properties. MPA-BTCA with CA anchoring groups exhibited stronger dipole moments and formed a homogeneous monolayer on the indium tin oxide(ITO) surface by adopting an upstanding self-assembling mode. However, the MPA-BT-RA molecules tend to aggregate severely in solid state due to the sp~3 hybridization of the carbon atom on the RA group, which is not favorable for achieving a long-range ordered self-assembled layer.Consequently, benefiting from high dipole moment, as well as dense and uniform self-assembled film,the device based on MPA-BT-CA yielded a remarkable power conversion efficiency(PCE) of 21.81%.Encouragingly, an impressive PCE approaching 20% can still be obtained for the MPA-BT-CA-based PSCs as the device area is increased to 0.80 cm^(2). Our work sheds light on the design principles for developing hole selecting SAMs, which will pave a way for realizing highly efficient, flexible, and large-area PSCs.

关键词： Self-assembled molecules Donor-acceptor backbones Hole contacts Perovskite solar cells Anchoring groups

Recent progress in low-cost noncovalently fused-ring electron acceptors for organic solar cells

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Aggregate 2022年第6期3卷 43-59页

作者： Qingqing Bai Qiming Liang Henan Li Huiliang Sun Xugang Guo Li Niu Center for Advanced Analytical Science School of Chemistry and Chemical EngineeringGuangzhou UniversityGuangzhouPR China Guangzhou Key Laboratory of Sensing Materials and Devices GuangzhouPR China Department of Materials Science and Engineering Southern University of Science and TechnologyShenzhenPR China

The power conversion efficiencies(PCEs)of organic solar cells(OSCs)have improved considerably in recent years with the development of fused-ring electron acceptors(FREAs).Currently,FREAs-based OSCs have achieved high PCEs of over 19%in single-junction OSCs.Whereas the relatively high synthetic complexity and the low yield of FREAs typically result in high production costs,hindering the commercial application of OSCs.In contrast,noncovalently fused-ring electron acceptors(NFREAs)can compensate for the shortcomings of FREAs and facilitate large-scale industrial production by virtue of the simple structure,facile synthesis,high yield,low cost,and reasonable efficiency.At present,OSCs based on NFREAs have exceeded the PCEs of 15%and are expected to reach comparable efficiency as FREAs-based OSCs.Here,recent advances in NFREAs in this review provide insight into improving the performance of OSCs.In particular,this paper focuses on the effect of the chemical structures of NFREAs on the molecule conformation,aggregation,and packing mode.Various molecular design strategies,such as core,side-chain,and terminal group engineering,are presented.In addition,some novel polymer acceptors based on NFREAs for all-polymer OSCs are also introduced.In the end,the paper provides an outlook on developing efficient,stable,and low-cost NFREAs for achieving commercial applications.

关键词： low cost noncovalently fused-ring electron acceptors organic solar cells

Polymer acceptors for all-polymer solar cells

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Journal of Semiconductors 2021年第8期42卷 4-7页

作者： Xiaofei Ji Zuo Xiao Huiliang Sun Xugang Guo Liming Ding Department of Materials Science and Engineering Southern University of Science and TechnologyShenzhen 518055China Center for Excellence in Nanoscience(CAS) Key Laboratory of Nanosystem and Hierarchical Fabrication(CAS)National Center for Nanoscience and TechnologyBeijing 100190China

Bulk-heterojunction polymer solar cells(PSCs)as a clean and renewable energy resource have attracted great attention from both academia and industry[1−20].Recently non-fullerene PSCs based on polymer donors(PDs)and small molecule acceptors(SMAs)have achieved remarkable success with the power conversion efficiencies(PCEs)over 18%[21−26].

关键词： polymer acceptors heterojunction