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axial enantiomers with donor-regulated TADF feature for multicolor circularly polarized electroluminescence

Science China Chemistry 2024年第6期67卷 2039-2045页

作者： Chen-Hao Guo Wen-Long Zhao Ke-Ke Tan Wei-Chen Guo Liheng Feng Chuan-Feng Chen Meng Li School of Chemistry and Chemical Engineering Shanxi UniversityTaiyuan030006China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of SciencesBeijing100190China University of Chinese Academy of Sciences Beijing100049China

This study optimized the TADF feature of axial chiral enantiomers through precise donor engineering,and multicolor CP-TADFwas achieved in the axial chiral framework.Three pairs of axial enantiomers with donor-regulated TADF feature,namely(R/S)-TPCBD,(R/S)-DPCBD,and(R/S)-DPACBD,were synthesized by introducing carbazole donors with different substituents onto biphenyl cyanide acceptors.As the electron-donating ability of donors increases,the emission of these axial enantiomers ranges from 455,476 to 552 nm,their singlet-triplet energy gaps(ΔE_(ST))gradually decrease from 0.30,0.22 to 0.02 e V,accompanied by an increasement in the transition rate(k_(RISC))of RISC process,and the k_(RISC)of DPACBD could reach up to 7.16×10^(5)s^(-1).These axial enantiomers also exhibit mirror-image CD and circularly polarized luminescence(CPL)properties.Moreover,OLEDs based on TPCBD,DPCBD,and DPACBD as emitter were then fabricated,which displayed blue,green,and orange electroluminescence with EQE_(max)of 13.0%,16.4%,and 25.0%,respectively.The results also exhibited a phenomenon of device efficiency increasing with the enhancement of donor abilities.Notably,the CP-OLEDs using(R/S)-TPCBD,(R/S)-DPCBD and(R/S)-DPACBD as emitters displayed intense CPEL signals with g_(EL)values of 3.4×10^(-3)/-4.1×10^(-3),3.2×10^(-3)/-3.1×10^(-3)and2.3×10^(-3)/-2.1×10^(-3),respectively.By convenient molecular engineering of donor regulation in the same molecular skeleton,CP-TADF materials with multicolor CPEL and improved device performance could be conveniently achieved.

关键词： axial chirality thermally activated delayed fluorescence circularly polarized luminescence electroluminescence organic light-emitting diodes

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Catalytic Enantioselective Simultaneous Control of axial chirality and Central chirality in Allenes

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Chinese Journal of Chemistry 2018年第5期36卷 387-391页

作者： Jianxin Dai Xinyu Duan Jing Zhou Chunling Fu Shengming Ma Laboratory of MolecuJar Recognition and Synthesis Department of Chemistry Zhejian8 University Hangzhou Zhejiang 310027 China

Chiral molecules, which may contain one or more different type（s） of stereocentres, such as central, axial, planar, and helical chiralities, etc., are indispensable in chemistry, pharmaceutical industry, and life science. Despite many advances for the preparation of chiral molecules usually with a single type of chirality have been realized, simultaneous construction of different types of chiralities is still a significant challenge. Here, we wish to report a protocol for preparation of chiral allenes with both central and axial chiralities via a catalytic asymmetric allenylation of different biologically or syn- thetically useful fluorinated or non-fluorinated nucleophiles with readily available racemic allenes by using a single chiral ligand. An echoing between the central chirality and axial chirality for the enantioselectivity was observed. This strategy provides a general and practical approach to functionalized optically active allenes bearing both central and axial chiralities with an excellent enantioselectivity under mild conditions.

关键词： chiral palladium catalysis axial chirality central chirality simultaneous control allene

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C_3-Symmetric Molecules with axial chirality and Handed Arrangement of Dipole Fields

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Chemical Research in Chinese Universities 2007年第5期23卷 628-630页

作者： XU Wei JIN Lan ZHOU Hui LU Yin-xiang LAN Bi-jian ZOU Zhen-guang Department of Materials Science Department of Chemistry Fudan University Shanghai 200433 P. R. China

Introduction chirality is defined as the absence of inversion symmetry,however,it is actually a pseudo-scalar of objects or figures,and does not depend for its definition on any connection to the physical world[1-5]. Logically,chiral molecules may possess other inherent physical quantity that guarantees the connection to the physical world[6,7].

关键词： C3 symmetry axial chirality Electric dipole Handed vortex field Two-state system

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Rhodium-catalyzed enantio-and diastereoselective carboamidation of bicyclic olefins toward construction of remote chiral centers and axis

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Science China Chemistry 2023年第7期66卷 2046-2052页

作者： Jinlei Wang Xingwei Li School of Chemistry and Chemical Engineering Shaanxi Normal University(SNNU)Xi’an 710062China

The precise control of multiple chiral elements through a single step catalytic process remains a significant challenge in asymmetric catalysis.Reported herein is rhodium-catalyzed three-component asymmetric carboamidation between aryl boronic acid,achiral strain-activated symmetric bicyclic olefins bearing a prochiral C-N or N-N axis,and dioxazolones.The reaction proceeded effectively in excellent enantio-and diastereoselectivity under mild conditions to produce the bicyclic framework with six contiguous chiral centers as well as a N-N or C-N chiral axis.The reaction featured excellent functional group tolerance,chemoselectivity,and stereoselectivity.Mechanistic studies indicated that the coupling system proceeded via initial transmetalation,followed by stereo-determining migratory insertion into the olefin and electrophilic amidation.

关键词： carboamidation axial chirality desymmetrization bicyclic olefin transmetalation

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Catalytic Asymmetric Synthesis of axially Chiral 3,3'-Bisindoles by Direct Coupling of Indole Rings

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Chinese Journal of Chemistry 2022年第18期40卷 2151-2160页

作者： Feng-Tao Sheng Shuang Yang Shu-Fang Wu Yu-Chen Zhang Feng Shi School of Chemistry and Materials Science Jiangsu Normal UniversityXuzhouJiangsu221116 China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiangHenan453007 China

Comprehensive Summary A new strategy for the enantioselective synthesis of axially chiral 3,3'-bisindoles was devised by the direct coupling of two indole rings.This strategy makes use of the C3-umpolung reactivity of 2-indolylmethanols,which enables the catalytic asymmetric addition reaction of 2-indolylmethanols with rationally designed 2-substituted indoles,thus constructing axially chiral 3,3'-bisindole scaffolds in overall excellent yields(up to 98%)with high enantioselectivities(up to 96:4 er).This approach not only has overcome the challenges in constructing axially chiral five-five-membered heterobiaryls,but also represents a new application of the C3-umpolung reactivity of 2-indolylmethanols in asymmetric catalysis.More importantly,this class of axially chiral 3,3'-bisindoles can undergo a variety of post-functionalizations to give axially chiral 3,3'-bisindole-based organocatalysts,which have found their preliminary applications in asymmetric catalysis.

关键词： Asymmetric catalysis Atroposelectivity axial chirality Organocatalysis Enantioselectivity

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Design and catalytic atroposelective synthesis of axially chiral isochromenone-indoles

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Science China Chemistry 2022年第10期65卷 1929-1937页

作者： Qing-Qing Hang Shu-Fang Wu Shuang Yang Xue Wang Zhen Zhong Yu-Chen Zhang Feng Shi Research Center of Chiral Functional Heterocycles School of Chemistry&Materials ScienceJiangsu Normal UniversityXuzhou 221116China School of Petrochemical Engineering Changzhou UniversityChangzhou 213164China

The catalytic atroposelective synthesis of axially chiral isochromenone-indoles has been established by the strategy of designing homophthalic anhydride-based indole derivatives as a new type of indole-based platform molecules for dynamic kinetic resolution.By this strategy,a wide range of axially chiral isochromenone-indoles were synthesized in high yields with excellent enantioselectivities(up to 98% yield,97% ee) via the catalytic asymmetric sulfonylation reaction of homophthalic anhydridebased indole derivatives with aryl sulfonyl chlorides under the catalysis of chiral quaternary ammonium salt as a phase-transfer catalyst.

关键词： asymmetric organocatalysis axial chirality atroposelectivity enantioselectivity indole

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Recent advances in the construction of axially chiral arylpyrroles

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中国科学:化学英文版 2023年第9期66卷 2480-2491页

作者： Yang-Bo Chen Ye-Nan Yang Xuan-Zhu Huo Long-Wu Ye Bo Zhou Key Laboratory of Chemical Biology of Fujian Province State Key Laboratory of Physical Chemistry of Solid SurfacesCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

Catalytic enantioselective preparation of axially chiral molecules has gained considerable interest over the past decades, due to their numerous applications in bioactive molecules, natural products, pharmaceuticals, materials, ligands, and catalysts. Compared with the well-established synthetic approaches for six-membered axially chiral skeletons, methodologies directed towards five-membered axially chiral compounds are relatively rare. Among these, axially chiral arylpyrroles are especially important structural motifs with wide utility, and the atroposelective synthesis of them is highly desirable. In recent years, novel strategies have been developed based on transition-metal catalysis and organocatalysis. This review summarizes the recent achievements in atroposelective preparation of arylpyrroles, by emphasizing the synthetic methods for each axially chiral framework, reaction mechanisms, and applications.

关键词： axial chirality pyrrole atropisomers transition-metal catalysis organocatalysis

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Design and synthesis of axially chiral aryl-pyrroloindoles via the strategy of organocatalytic asymmetric(2+3)cyclization

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Fundamental Research 2023年第2期3卷 237-248页

作者： Ping Wu Lei Yu Cong-Hui Gao Qi Cheng Shuang Deng Yinchun Jiao Wei Tan Feng Shi School of Chemistry and Materials Science Jiangsu Normal UniversityXuzhou 221116China School of Chemistry and Chemical Engineering Hunan University of Science and TechnologyXiangtan 411201China

The catalytic asymmetric construction of axially chiral indole-based frameworks is an important area of research due to the unique characteristics of such frameworks.Nevertheless,research in this area is still in its infancy and has some challenges,such as designing and constructing new classes of axially chiral indole-based scaffolds and developing their applications in chiral catalysts,ligands,etc.To overcome these challenges,we present herein the design and atroposelective synthesis of aryl-pyrroloindoles as a new class of axially chiral indole-based scaffolds via the strategy of organocatalytic asymmetric(2+3)cyclization between 3-arylindoles and propargylic alcohols.More importantly,this new class of axially chiral scaffolds was derived into phosphines,which served as efficient chiral ligands in palladium-catalyzed asymmetric reactions.Moreover,theoretical calculations provided an in-depth understanding of the reaction mechanism.This work offers a new strategy for constructing axially chiral indole-based scaffolds,which are promising for finding more applications in asymmetric catalysis.

关键词： Asymmetric organocatalysis axial chirality Indole Atroposelectivity Enantioselectivity Cyclization

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axially Chiral Dodecanuclear Lanthanide Clusters Constructed by“Bottom-Up” Self-assembly for Enantioselective Sensing

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Chinese Journal of Chemistry 2022年第10期40卷 1165-1170页

作者： Honglei Zhao Dongxu Cui Junning Kou Haijuan Gao Guanghui Yu Chunyi Sun Xinlong Wang Zhongmin Su Key Laboratory of Polyoxometalate Science of Ministry of Education Northeast Normal UniversityChangchunJilin 130024China

Via the bottom-up synthetic strategy,we synthesized a pair of dodecanuclear metal clusters of Eu_(12)(C_(2)O_(4))_(9)(R/S-BNP)_(18)(EtOH)_(6)-(H_(2)0)_(6)·8EtOH-7H_(2)0(complex 2),which represent the largest axial chiral lanthanide metal clusters.In the structure,rare four-pointed star coordination mode of oxalic acid is reported by this work.In addition,as a fluorescence sensor,the complex 2 exhibits high enantioselectivity for R-/S-BINOL-TF_(2)(EF=2.87)and other chiral binaphthyl derivatives.

关键词： axial chirality Cluster compounds Molecular recognition Self-assembly Host-guest systems

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Diversity-Oriented Enantioselective Construction of Atropisomeric Heterobiaryls and N-Aryl Indoles via Vinylidene Ortho-Quinone Methides

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CCS Chemistry 2022年第8期4卷 2686-2697页

作者： Da Xu Shengli Huang Fangli Hu Lei Peng Shiqi Jia Hui Mao Xiangnan Gong Fenglan Li Wenling Qin Hailong Yan Chongqing Key Laboratory of Natural Product Synthesis and Drug Research School of Pharmaceutical SciencesChongqing UniversityChongqing 401331 College of Pharmacy Jinhua PolytechnicJinhuaZhejiang Province 321007 Analytical and Testing Center of Chongqing University Chongqing UniversityChongqing 401331 Anqiu Women and Children’s Hospital AnqiuShandong Province 262102

An atroposelectively diversity-oriented synthetic strategy was developed for the divergent synthesis of axially chiral heterocycles through organocatalytic asymmetric intramolecular annulation of alkyne via vinylidene ortho-quinone methides(VQMs).The methodology reported herein was characterized by rapid reactions(most completed in seconds),high stereocontrol(up to 98%ee),and broad substrate scope(60 examples of different skeletal types,stereogenicelements,andring sizes).

关键词： asymmetric catalysis organocatalysis atroposelectivity axial chirality heteroannulation

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