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Transfer, Amplification, Storage, and Complete Self-Recovery of Supramolecular Chirality in an Achiral polymer System

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Angewandte Chemie 2021年第34期133卷

作者： Tengfei Miao Xiaoxiao Cheng Haotian Ma Zixiang He Prof. Zhengbiao Zhang Prof. Nianchen Zhou Prof. Wei Zhang Prof. Xiulin Zhu State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 China

Supramolecular chirality and its complete self-recovery ability are highly mystical in nature and biological systems, which remains a major challenge today. Herein, we demonstrate that partially cross-linked azobenzene (Azo) units can be employed as the potential chiral trigger to fully heal the destroyed helical superstructure in achiral nematic polymer system. Combining the self-assembly of Azo units and terminal hydroxyl groups in polymer side chains allows the vapor-induced chiral nematic phase and covalent fixation of the superstructure via acetal reaction. The induced helical structure of Azo units can be stored by inter-chain cross-linking, even after removal of the chiral source. Most interestingly, the stored chiral information can trigger perfect chiral self-recovery (CSR) behavior after being destroyed by UV light, heat, and solvents. The results pave a new way for producing novel chiroptical materials with reversible chirality from achiral sources.

关键词： chiral induction chiral self-recovery chiral storage supramolecular chirality

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Iodonium Initiators: Paving the Air-free Oxidation of Spiro-OMeTAD for Efficient and Stable Perovskite Solar Cells

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Angewandte Chemie 2023年第5期136卷

作者： Heyi Yang Tingting Xu Weijie Chen Yeyong Wu Xianming Guo Yunxiu Shen Chengqiang Ding Xining Chen Haiyang Chen Junyuan Ding Xiaoxiao Wu Prof. Guixiang Zeng Prof. Zhengbiao Zhang Prof. Yaowen Li Prof. Yongfang Li Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor-optoelectronics Materials and Devices College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 China School of Chemistry and Chemical Engineering Nanjing University Nanjing 210008 China State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 China Kuang Yaming Honors School Nanjing University Nanjing 210008 China State Key Laboratory of Radiation Medicine and Protection Soochow University Suzhou 215123 China Jiangsu Key Laboratory of Advanced Negative Carbon Technologies Soochow University Suzhou 215123 China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China

To date, perovskite solar cells (pero-SCs) with doped 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD) hole transporting layers (HTLs) have shown the highest recorded power conversion efficiencies (PCEs). However, their commercialization is still impeded by poor device stability owing to the hygroscopic lithium bis(trifluoromethanesulfonyl)imide and volatile 4-tert-butylpyridine dopants as well as time-consuming oxidation in air. In this study, we explored a series of single-component iodonium initiators with strong oxidability and different electron delocalization properties to precisely manipulate the oxidation states of Spiro-OMeTAD without air assistance, and the oxidation mechanism was clearly understood. Iodine (III) in the diphenyliodonium cation (IP + ) can accept a single electron from Spiro-OMeTAD and forms Spiro-OMeTAD⋅ + owing to its strong oxidability. Moreover, because of the coordination of the strongly delocalized TFSI − with Spiro-OMeTAD⋅ + in a stable radical complex, the resulting hole mobility was 30 times higher than that of pristine Spiro-OMeTAD. In addition, the IP-TFSI initiator facilitated the growth of a homogeneous and pinhole-free Spiro-OMeTAD film. The pero-SCs based on this oxidizing HTL showed excellent efficiencies of 25.16 % (certified: 24.85 % for 0.062-cm 2 ) and 20.71 % for a 15.03-cm 2 module as well as remarkable overall stability.

关键词： Doping Perovskite Solar Cells Spiro-OMeTAD Stability

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Tracking the multiple-step formation of an iron(Ⅲ) complex and its application in photodynamic therapy for breast cancer

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Science China Chemistry 2019年第6期62卷 719-726页

作者： Zhong-Hong Zhu Qian Hu Hui-Ling Pan Yuexing Zhang Haibing Xu Mohamedally Kurmoo Jin Huang Ming-Hua Zeng Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources School of Chemistry and Pharmaceutical SciencesGuangxi Normal University Shanghai Key Laboratory of New Drug Design School of Pharmacy East China University of Science and Technology Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules College of Chemistry and Chemical Engineering Hubei University Université de Strasbourg Institut de Chimie de Strasbourg CNRS-UMR7177 4 rue Blaise Pascal

A tandem reaction of pyridin-2-ylmethanamine(L1′) with 8-hydroxyquinoline-2-carbaldehyde(HL1) assisted by FeCl_3 was observed to give the new nitrogen heterocycle HL3(HL3=2-(imidazo[1,5-a]pyridin-3-yl)quinolin-8-ol) as its Fe(Ⅲ) complex,[Fe(L3)Cl_2](Fe1). Electrospray ionization mass spectrometry(ESI-MS) reveals its formation involves three steps:(1) coordination of both HL1 and L1′ to Fe,(2) aldehyde-amine coupling, and(3) ring closure. The results of electronic absorption spectroscopy, cyclic voltammetry, and density functional theory(DFT) calculations show the proximity of the optical transition energy to that of the excitation of ~3O_2 to ~1O_2, which prompted us to explore its application as a photosensitizer for photodynamic therapy(PDT). Photo-toxicity studies show that Fe1 exhibits the highest anti-proliferation efficiency in human breast cancer MDA-MB-231 cells under light irradiation. Moreover, studies with orthotopic models of breast cancer further expounded the anti-tumor activity of Fe1 with no significant toxicity to other organs and low retention in the body.

关键词： tandem formation iron(Ⅲ) complex DFT calculation photodynamic therapy breast cancer

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Multiple Effects Tailoring the Self-organization Behaviors of Triphenylene Side-chain Liquid Crystalline polymers via Changing the Spacer Length

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Chinese Journal of polymer Science 2018年第8期36卷 960-969页

作者： Xiang-Hui Han Xi-Wen Yang Sheng Chen Hang Luo Dou Zhang Hai-Liang Zhang Key Laboratory of Polymeric Materials and Application Technology of Hunan Province Key Laboratory of Advanced Functional Polymer Materials of Colleges and Universities of Hunan ProvinceCollege of ChemistryXiangtan University State Key Laboratory of Powder Metallurgy Central South University

Long-alkyl tail triphenylene （TP） side-chain liquid crystalline polymers （SCLCPs） with different spacer length （P-m-TP, m = 2, 3, 4, 6, 8, which is the number of carbon atom in the flexible alkyl spacers） have been successfully synthesized via free radical polymerization. The differential scanning calorimetry （DSC）, polarized light microscopy （POM）, ultraviolet-visible spectroscopy （UV- Vis）, wide-angle X-ray diffraction （WAXD） and small-angle X-ray scattering （SAXS） measurements were performed to investigate the influence of multiple effects on the self-organization behaviors of P-m-TP, including steric effect, decoupling effect and π-π stacking effect. The experimental results revealed that P-m-TP （m = 2, 3, 4） formed the columnar phase which was developed by the TP moieties and the main chain as a whole, suggesting that the side-chains had strong steric effect even though the number of spacer length （m） exceeded 4. In addition, the clearing points （Tis） of the polymers were above 300 ℃. When m = 6 and 8, the polymers displayed hexagonal columnar phase and exhibited the low Tis （91 and 80 ℃ respectively）, originating from the self-assembly of triphenylene due to the decoupling effect and π-π stacking effect. This work offers a viable and inspiring pathway to control the phase transition temperature and phase structure ofTP SCLCPs via simply tailoring the spacer length and increasing the alkyl tail length of TP.

关键词： polymer synthesis Side-chain liquid crystalline polymers Phase structure Steric effect

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Flame-retardant single-component epoxy resin cured by benzimidazolyl-substituted cyclotriphosphazene: Storage stability, curing behaviors and flame retardancy

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polymer Degradation and Stability 2022年 204卷

作者： Hu, Ben Wang, Jun Wang, Jingsheng Yang, Shuang Li, Chang Wang, Fengyi Huo, Siqi Song, Pingan Fang, Zhengping Wang, Hao School of Materials Science and Engineering Wuhan University of Technology Wuhan430070 China School of Mechanical and Electronic Engineering Wuhan University of Technology Wuhan430070 China Department of Mechanical Engineering City & Guilds Building South Kensington Campus Imperial College London LondonSW7 2AZ United Kingdom Hubei Collaborative Innovation Centre for Advanced Organic Chemical Materials and Ministry of Education Key Laboratory for the Green Preparation and Application of Functional Materials Hubei University Wuhan430062 China Laboratory of Polymer Materials and Engineering NingboTech University Ningbo315100 China Center for Future Materials University of Southern Queensland Springfield4300 Australia

This work reported a flame-retardant single-component epoxy resin via the integration of two bisphenol-A-type epoxy resins (E20 and E53) and benzimidazolyl-substituted cyclotriphosphazene (BICP). The differential scanning calorimetry (DSC) tests showed that the onset curing temperature of E53/E20/BICP was 30°C lower than that of E53/BICP due to the catalytic decomposition effect of E20 towards BICP under heating. Besides, the shelf life of E53/E20/BICP at room temperature reached ∼40 days, demonstrating good storage stability. E53/E20/BICP maintained satisfactory thermal properties and showed outstanding flame retardancy with a UL-94 V-0 classification. Compared with the unmodified EP sample, the peak heat release rate (PHRR) and total heat release (THR) of E53/E20/BICP were decreased by ∼64.1% and ∼39.0%, respectively. Hence, this flame-retardant single-component EP with satisfactory comprehensive properties exhibited great potential for versatile industrial applications. © 2022

关键词： Curing

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Photocatalytic Hydroxylation and Oxidative Coupling Reactions Mediated by Multinuclear Au(I) Supramolecular Clusters

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Angewandte Chemie 2024年第8期137卷

作者： Qing-Ya Sun Hui-Zhen He Ying Zhou Yu-Peng Dai Ping Shang Dr. Xuan-Feng Jiang Key Laboratory of Green Preparation and Application for Functional Materials Ministry of Education Collaborative Innovation Center for Advanced Organic Chemical Materials Co-constructed by the Province and Ministry Hubei Key Laboratory of Polymer Science School of Materials Science and Engineering Hubei University Wuhan Hubei 430062 P. R. China Department of Chemistry and Environmental Engineering Hubei Minzu University Enshi Hubei 445000 P. R. China

Polynuclear Au(I) cluster photocatalysts, known for their high activity and stability, hold substantial potential in organic synthetic chemistry. This study synthesized two Au(I) supramolecular cluster catalysts with different nuclearities: a tetranuclear cluster, C1 ([(dppmAu 2 ) 2 L 1 ] • PF 6 − ), and a hexadecanuclear cluster, C2 [(dppmAu 2 ) 6 (Au 4 )( L 1 ) 4 ] • 4PF 6 − , through a multicomponent stepwise self-assembly approach. Both cluster structures feature aurophilicity interaction motifs that endow them with exceptional photocatalytic performance, exhibiting optical band gaps of 2.27 eV and 2.41 eV, respectively. Upon photoexcitation, these clusters efficiently generate reactive oxygen species, significantly enhancing their photocatalytic efficacy for the oxidative hydroxylation of phenylboronic acids and oxidative coupling of benzylamines under mild conditions. Catalytic efficiencies exceeding 90 % were achieved. Turnover frequencies for C2 and C1 were measured at 52.045 h −1 and 6.030 h −1 , respectively, representing the highest efficiencies reported for photocatalysts to date. Compared to C1 , C2 exhibited superior photocatalytic activity, attributed to its higher photoelectric sensitivity and greater exposure of active metal sites. Using a combination of experimental data and density functional theory calculations, the plausible mechanisms were proposed for two photocatalytic reactions. This study demonstrates that the use of multicomponent cooperative self-assembly strategy to synthesize high-nuclearity Au(I) clusters offers innovative pathways for the development of efficient, green, light-driven organic synthesis.

关键词： Au(I) complex Photocatalysis Cluster catalysts Multiple active sites

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Self-promoted Controlled Ring-opening polymerization via Side Chain-mediated Proton Transfer for the Synthesis of Tertiary Amine-pendant Polypeptoids

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Angewandte Chemie 2024年第6期137卷

作者： Mingzhen Liao Yao Yao Kunyu Gan Xianghua Su Ning Zhao Ronald N. Zuckermann Sunting Xuan Zhengbiao Zhang State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials Jiangsu Key Laboratory of Advanced Functional Polymer Materials Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 China Suzhou GenePharma Co. Ltd. Suzhou 215123 China College of Pharmaceutical Sciences Soochow University Suzhou 215123 China. The Molecular Foundry Lawrence Berkeley National Laboratory 1 Cyclotron Road Berkeley California 94720 United States State Key Laboratory of Radiation Medicine and Protection Soochow University Suzhou 215123 China

Proton transfer is essential in virtually all biochemical processes, with enzymes facilitating this transfer by optimizing the proximity and orientation of reactants through site-specific hydrogen bonds. Proton transfer is also crucial in the rate-determining step for the ring-opening polymerization of N -carboxyanhydrides (NCAs), widely used to prepare various peptidomimetic materials. This study utilizes side chain-assisted strategy to accelerate the rate of chain propagation by using NCAs with tertiary amine pendants. This moiety enables hydrogen bond formation between the incoming NCA and the polymer amino growing end. The tertiary amine side chain of the NCA forms a proton shuttle, via a less constrained transition state, to facilitate the proton transfer process. Moreover, the tertiary amine side chains enable the precipitation of NCA monomers through in situ protonation during the monomer synthesis. This greatly facilitates the synthesis of these unreported monomers, allowing the direct controlled synthesis of tertiary amine-pendant polypeptoids. This side chain-promoted polymerization has rarely been reported. Additionally, the tertiary amine side chains, as widely used functional groups, endow the polymers with unique properties including pH- and thermo-responsiveness, tunable p K a s, and siRNA transfection capability. The self-promoted synthesis, facile monomer preparation, and attractive properties make tertiary amine-pendant polypeptoids promising materials for various applications.

关键词： Self-promoted Side chain-promoted Proton transfer Tertiary amine-pendant Polypeptoids Controlled ring-opening polymerization

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Organocatalytic Lithium Chloride Oxidation by Covalent Organic Frameworks for Rechargeable Lithium-Chlorine Batteries

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Angewandte Chemie 2023年第7期136卷

作者： Dr. Yan Xu Mingming Wang Muhammad Sajid Yahan Meng Zehui Xie Lidong Sun Prof. Jian Jin Prof. Wei Chen Dr. Shenxiang Zhang College of Energy Soochow Institute for Energy and Materials Innovations Light Industry Institute of Electrochemical Power Sources Key Laboratory of Advanced Carbon Materials and Wearable Energy Technologies of Jiangsu Province Soochow University Suzhou Jiangsu 215006 China Department of Applied Chemistry School of Chemistry and Materials Science Hefei National Research Center for Physical Sciences at the Microscale University of Science and Technology of China Hefei Anhui 230026 China College of Chemistry Chemical Engineering and Materials Science Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application Jiangsu Key Laboratory of Advanced Negative Carbon Technologies Soochow University Suzhou Jiangsu 215123 China

Rechargeable Li−Cl 2 battery is a promising high energy density battery system. However, reasonable cycle life could only be achieved under low specific capacities due to the sluggish oxidation of LiCl to Cl 2 . Herein, we propose an amine-functionalized covalent organic framework (COF) with catalytic activity, namely COF−NH 2 , that significantly decreases the oxidation barrier of LiCl and accelerates the oxidation kinetics of LiCl in Li−Cl 2 cell. The resulting Li−Cl 2 cell using COF−NH 2 (Li−Cl 2 @COF−NH 2 ) simultaneously exhibits low overpotential, ultrahigh discharge capacity up to 3500 mAh/g and a promoted utilization ratio of deposited LiCl at the first cycle (UR−LiCl) of 81.4 %, which is one of the highest reported values to date. Furthermore, the Li−Cl 2 @COF−NH 2 cell could be stably cycled for over 200 cycles when operating at a capacity of 2000 mAh/g at −20 °C with a Coulombic efficiency (CE) of ≈100 % and a discharge plateau of 3.5 V. Our superior Li−Cl 2 batteries enabled by organocatalyst enlighten an arena towards high-energy storage applications.

关键词： Covalent Organic Framework High Energy Density Lithium Chloride Oxidation Lithium-Chlorine Battery Organocatalysis

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Correction: Interfacial engineering between SnO2/MAPbI3 by maleate pheniramine halides toward carbon counter electrode-based perovskite solar cells with 16.21% efficiency

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Materials Chemistry Frontiers 2023年第6期7卷 1153-1153页

作者： Duoling Cao Zuhong Li Wenbo Li Ke Pei Xu Zhang Li Wan Li Zhao Alexey Cherevan Dominik Eder Shimin Wang Key Laboratory for the Green Preparation and Application of Functional Materials Ministry of Education Hubei Key Laboratory of Polymer Materials Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials Faculty of Materials Science and Engineering Hubei University Wuhan 430062 P. R. China Institute of Materials Chemistry Technische Universität Wien Getreidemarkt 9/165 1060 Vienna Austria

Correction for ‘Interfacial engineering between SnO2/MAPbI3 by maleate pheniramine halides toward carbon counter electrode-based perovskite solar cells with 16.21% efficiency’ by Duoling Cao et al., Mater. Chem. Fro...

Correction for ‘Interfacial engineering between SnO₂/MAPbI₃ by maleate pheniramine halides toward carbon counter electrode-based perovskite solar cells with 16.21% efficiency’ by Duoling Cao et al., Mater. Chem. Front., 2023, https://***/10.1039/d2qm01149b.

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Molecular Self-Assembly Regulated Dopant-Free Hole Transport Materials for Efficient and Stablen-i-pPerovskite Solar Cells and Scalable Modules

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Angewandte Chemie 2022年第42期134卷

作者： Qinrong Cheng Haiyang Chen Fu Yang Ziyuan Chen Weijie Chen Heyi Yang Yunxiu Shen Xue-Mei Ou Yeyong Wu Prof. Yaowen Li Prof. Yongfang Li Laboratory of Advanced Optoelectronic Materials Suzhou Key Laboratory of Novel Semiconductor-optoelectronics Materials and Devices College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 China State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 China Jiangsu Key Laboratory of Advanced Negative Carbon Technologies Soochow University Suzhou 215123 China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China

Dopant-free organic hole transport materials (HTMs) remain highly desirable for stable and efficient n - i - p perovskite solar cells (pero-SCs) but rarely succeed. Here, we propose a molecular assembly strategy to overcome the limited optoelectronic properties of organic HTMs by precisely designing a linear organic small molecule BDT-DPA-F from the atomic to the molecular levels. BDT-DPA-F can assemble into a fibril network, showing an obviously improved hole mobility and decreased energy disorder. The resultant pero-SCs showed a promising efficiency of 23.12 % (certified 22.48 %), which is the highest certified value of pero-SCs with dopant-free HTMs, to date. These devices also showed a weak-dependence of efficiency on size, enabling a state-of-the-art efficiency of 22.50 % for 1-cm 2 device and 20.17 % for 15.64-cm 2 module. For the first time, the pero-SCs based on dopant-free HTMs realized ultralong stabilities with T 80 lifetimes over 1200 h under operation or thermal aging at 85 °C.

关键词： Dopant-Free Hole Transport Materials Intermolecular Interactions Operational and Thermal Stabilities Perovskite Solar Cells Self-Assembly

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