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学者姓名：廖赛虎
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Abstract ：
The development of visible light-regulated polymerizations for precision synthesis of polymers has drawn considerable attention in the past years. In this study, an ancient dye, indigo, is successfully identified as a new and efficient photoacid catalyst, which can readily promote the ring-opening polymerization of lactones under visible light irradiation in a well-controlled manner, affording the desired polyester products with predictable molecular weights and narrow dispersity. The enhanced acidity of indigos by excitation is crucial to the H-bonding activation of the lactone monomers. Chain extension and block copolymer synthesis are also demonstrated with this method. An ancient dye, indigo, is applied to lactone ring-opening polymerization. The excited state acidity of the indigo photocatalyst is utilized to induce hydrogen bond-mediated bifunctional activation, which efficiently catalyzes the visible light-mediated ring-opening polymerization of lactones. image
Keyword ：
indigo indigo photoacid photoacid photopolymerization photopolymerization ring-opening polymerization ring-opening polymerization visible light visible light
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| GB/T 7714 | Sun, Pan , Li, Zixuan , Zhang, Xun et al. Visible Light-Regulated Ring-Opening Polymerization of Lactones by Employing Indigo as a Photoacid Catalyst [J]. | MACROMOLECULAR RAPID COMMUNICATIONS , 2024 . |
| MLA | Sun, Pan et al. "Visible Light-Regulated Ring-Opening Polymerization of Lactones by Employing Indigo as a Photoacid Catalyst" . | MACROMOLECULAR RAPID COMMUNICATIONS (2024) . |
| APA | Sun, Pan , Li, Zixuan , Zhang, Xun , Liao, Yun , Liao, Saihu . Visible Light-Regulated Ring-Opening Polymerization of Lactones by Employing Indigo as a Photoacid Catalyst . | MACROMOLECULAR RAPID COMMUNICATIONS , 2024 . |
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In recent years, organophotocatalytic polymerizations have received significant interest as they enable metal-free and highly efficient macromolecular syntheses. Herein, we disclose the development of N-arylacridinium salts as an effective class of photocatalysts that could mediate the cationic reversible addition-fragmentation chain transfer (RAFT) polymerization of vinyl ethers with visible light regulation. Owing to their high stability and matched redox potentials with trithiocarbonate chain transfer agents, N-arylacridinium salts are capable of achieving excellent temporal control over this cationic RAFT polymerization at room temperature under the regulation of blue and green light.
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| GB/T 7714 | Liu, Haonan , Chen, Jianxu , Yang, Zan et al. Light-Controlled Cationic RAFT Polymerization of Vinyl Ethers Using N-Arylacridinium Photocatalysts [J]. | MACROMOLECULES , 2024 , 57 (8) : 3751-3756 . |
| MLA | Liu, Haonan et al. "Light-Controlled Cationic RAFT Polymerization of Vinyl Ethers Using N-Arylacridinium Photocatalysts" . | MACROMOLECULES 57 . 8 (2024) : 3751-3756 . |
| APA | Liu, Haonan , Chen, Jianxu , Yang, Zan , Jiang, Liuyin , Liu, Wenya , Ma, Jun-An et al. Light-Controlled Cationic RAFT Polymerization of Vinyl Ethers Using N-Arylacridinium Photocatalysts . | MACROMOLECULES , 2024 , 57 (8) , 3751-3756 . |
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Abstract ：
The tacticity of vinyl polymers is a key factor affecting the properties of materials. Recently, organic Bronsted acids have been demonstrated as effective catalysts for the development of highly stereoselective cationic reversible addition-fragmentation chain transfer (RAFT) polymerizations of vinyl ethers, in which the use of RAFT agents could allow the control the molecular weight and tacticity of polymer products simultaneously. However, the effect of RAFT agents on the tacticity-regulation remains elusive and lacks of investigation. In this study, we synthesized four types of RAFT agents and evaluated their influence in the stereoselective cationic polymerization of isobutyl vinyl ether in the presence of PADI as a Bronsted acid catalyst, which unveils that the Z group of RAFT agents could not only affect the polydispersity of the products, but also exert a profound effect on the stereoselectivity. After extensive screening of the RAFT agents, high stereoregularity (isotacticity, 90% m) was obtained when using dithiocarbonate ester-type RAFT agents with a benzyloxy Z group.
Keyword ：
Bronsted acid catalysis Bronsted acid catalysis Chain transfer agents Chain transfer agents RAFT polymerization RAFT polymerization Stereoselective cationic polymerization Stereoselective cationic polymerization Tacticity Tacticity
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| GB/T 7714 | Zhang, Zheng-Yi , Yang, Zan , Liao, Yun et al. Organic Brønsted Acid-Catalyzed Stereoselective Cationic RAFT Polymerization: The Effect of RAFT Agents [J]. | CHINESE JOURNAL OF POLYMER SCIENCE , 2024 , 42 (6) : 711-717 . |
| MLA | Zhang, Zheng-Yi et al. "Organic Brønsted Acid-Catalyzed Stereoselective Cationic RAFT Polymerization: The Effect of RAFT Agents" . | CHINESE JOURNAL OF POLYMER SCIENCE 42 . 6 (2024) : 711-717 . |
| APA | Zhang, Zheng-Yi , Yang, Zan , Liao, Yun , Liao, Sai-Hu . Organic Brønsted Acid-Catalyzed Stereoselective Cationic RAFT Polymerization: The Effect of RAFT Agents . | CHINESE JOURNAL OF POLYMER SCIENCE , 2024 , 42 (6) , 711-717 . |
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By virtue of noninvasive regulations by light, photocontrolled polymerizations have attracted considerable attention for the precision synthesis of macromolecules. However, a cationic polymerization with simultaneous photocontrol and tacticity-regulation remains elusive so far. Herein, we introduce an asymmetric ion-pairing photoredox catalysis strategy that allows for the development of a stereoselective cationic polymerization with concurrent light regulation for the first time. By employing an ion pair catalyst (PC+/*A(-)) consisting of a photoredox active cation (PC+) and a sterically confined chiral anion (*A-) to deliver the stereochemical control, the cationic polymerization of vinyl ethers can be achieved with photocontrol and high isotactic selectivity (up to 91% m) at a remarkable low catalyst loading (50 ppm).
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| GB/T 7714 | Yang, Zan , Liao, Yun , Zhang, Zhengyi et al. Asymmetric Ion-Pairing Photoredox Catalysis for Stereoselective Cationic Polymerization under Light Control [J]. | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (10) : 6449-6455 . |
| MLA | Yang, Zan et al. "Asymmetric Ion-Pairing Photoredox Catalysis for Stereoselective Cationic Polymerization under Light Control" . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146 . 10 (2024) : 6449-6455 . |
| APA | Yang, Zan , Liao, Yun , Zhang, Zhengyi , Chen, Jianxu , Zhang, Xun , Liao, Saihu . Asymmetric Ion-Pairing Photoredox Catalysis for Stereoselective Cationic Polymerization under Light Control . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (10) , 6449-6455 . |
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The incorporation of sulfonyl fluoride groups into molecules has been proved effective to enhance their biological activities or introduce new functions. Herein, we report a transition-metal-free and visible-light-mediated radical 1-fluorosulfonyl-2-heteroarylation of alkenes, which could allow access to a series of SO2F-containing quinoxalin-2(1H)-ones, which are a critical structural motif widely present in a number of biologically active molecules. Further application of the method to the modification of other heterocycles and drug molecules as well as ligation chemistry via SuFEx click reactions is also demonstrated.
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| GB/T 7714 | Lin, Lu , Wang, Peng , Dong, Tao et al. Radical Fluorosulfonyl Heteroarylation of Unactivated Alkenes with Quinoxalin-2(1H)-ones and Related N [J]. | ORGANIC LETTERS , 2023 . |
| MLA | Lin, Lu et al. "Radical Fluorosulfonyl Heteroarylation of Unactivated Alkenes with Quinoxalin-2(1H)-ones and Related N" . | ORGANIC LETTERS (2023) . |
| APA | Lin, Lu , Wang, Peng , Dong, Tao , Tsui, Gavin Chit , Liao, Saihu . Radical Fluorosulfonyl Heteroarylation of Unactivated Alkenes with Quinoxalin-2(1H)-ones and Related N . | ORGANIC LETTERS , 2023 . |
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Abstract ：
The advancement in the synthesis of functional polymeric materials has greatly benefited from the development of functionalized monomers and effective polymerization methods. Here, inspired by the controlled radical polymerization and the new generation of click chemistry, sulfur(VI) fluoride exchange (SuFEx), we introduce a SuFExable vinyl monomer, 4-vinylbenzenesulfonyl fluoride (VBSF), which shows a good balance of stability and reactivity and can readily undergo organocatalytic atom-transfer radical polymerization under visible light with good controls and high end-group fidelity, while retaining the sulfonyl fluoride groups intact. Moreover, poly(VBSF) can be further modified with high efficiency via SuFEx reactions with various aryl silyl ethers, thus allowing a rapid construction of a functional polymer library in a click fashion.
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| GB/T 7714 | Li, Meng , Ma, Jun-An , Liao, Saihu . Atom-Transfer Radical Polymerization of a SuFExable Vinyl Monomer and Polymer Library Construction via SuFEx Click Reaction [J]. | MACROMOLECULES , 2023 : 806-814 . |
| MLA | Li, Meng et al. "Atom-Transfer Radical Polymerization of a SuFExable Vinyl Monomer and Polymer Library Construction via SuFEx Click Reaction" . | MACROMOLECULES (2023) : 806-814 . |
| APA | Li, Meng , Ma, Jun-An , Liao, Saihu . Atom-Transfer Radical Polymerization of a SuFExable Vinyl Monomer and Polymer Library Construction via SuFEx Click Reaction . | MACROMOLECULES , 2023 , 806-814 . |
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Abstract ：
Vinyl polymer tacticity is critical for regulating the thermal and physical properties of materials. Stereoselective cationic polymerization of vinyl ethers has gained significant progress in recent years, while monomer scope beyond simple alkyl vinyl ethers to access functionalized isotactic polymer materials remains to be explored but highly desirable. Herein, we report the successful development of a stereoselective cationic polymerization of alkenyl vinyl ethers by employing confined Bronsted acid organocatalysis. This organocatalytic system shows high efficiency and stereoselectivity in the polymerization of several alkenyl vinyl ethers, as well as good compatibility to the diolefinic monomers without touching the C = C bonds in the alkenyl part during the cationic polymerization, thus allowing for further modification on these C-C double bonds after polymerization to construct functionalized, isotactic polymer materials. Further, a series of thermoplastic copolymers with tunable properties and variable and predictable contents of side-chain C = C bonds can be synthesized through the corresponding stereoselective copolymerization. Sequential post-polymerization modification of both isotactic homopolymers and copolymers by combining thiol-ene and sulfur(VI) fluoride exchange (SuFEx) click reactions is also demonstrated.
Keyword ：
Cationic polymerization Cationic polymerization Click reactions Click reactions Stereoselective polymerization Stereoselective polymerization Tacticity Tacticity Vinyl ethers Vinyl ethers
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| GB/T 7714 | Zhu, Hui , Jiang, Yu , Yang, Zan et al. Organocatalytic stereoselective cationic polymerization of alkenyl vinyl ethers and post-functionalization via click chemistry [J]. | GIANT , 2023 , 14 . |
| MLA | Zhu, Hui et al. "Organocatalytic stereoselective cationic polymerization of alkenyl vinyl ethers and post-functionalization via click chemistry" . | GIANT 14 (2023) . |
| APA | Zhu, Hui , Jiang, Yu , Yang, Zan , Zhang, Xun , Liao, Saihu . Organocatalytic stereoselective cationic polymerization of alkenyl vinyl ethers and post-functionalization via click chemistry . | GIANT , 2023 , 14 . |
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The synthesis, properties, and application of carbonyl-bridged phenanthrene, namely phenanthrenone, are described. A novel synthetic route involving palladium-catalyzed annulation between 4,5-dibromo-9-fluorenone and internal alkynes was developed to streamline the synthesis of phenanthrenone, an underexplored building block. The reaction tolerates a variety of substituents on the alkynes and provides moderate yields. Phenanthrenone derivatives possess the advantages of both fluorenone and phenanthrene backbones, such as extended conjugation, good planarity and rigidity, and tunable energy gaps. These attractive features make phenanthrenone an ideal electron-deficient & pi;-building block for developing novel polycyclic aromatic hydrocarbons. In addition, phenanthrenone derivatives can serve as organic photoredox catalysts for organocatalytic atom transfer radical polymerization and oxidation of alcohol.
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| GB/T 7714 | Gan, Ziyang , Zhou, Jie , Zhu, Lingyun et al. Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst [J]. | ORGANIC CHEMISTRY FRONTIERS , 2023 , 10 (15) : 3830-3836 . |
| MLA | Gan, Ziyang et al. "Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst" . | ORGANIC CHEMISTRY FRONTIERS 10 . 15 (2023) : 3830-3836 . |
| APA | Gan, Ziyang , Zhou, Jie , Zhu, Lingyun , Chen, Xinyu , Ma, Qiang , Yan, Jianfeng et al. Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst . | ORGANIC CHEMISTRY FRONTIERS , 2023 , 10 (15) , 3830-3836 . |
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Harnessing the excited state acidity of aromatic alcohols is emerging as an effective approach for the development of ring-opening polymerization (ROP) of lactones with additional control by light. In view of the wide presence of phenoxy moieties in many organic dyes, we herein explore a series of common and commercially available organic dyes as potential photoacid promotors for the ROP of lactones. Several organic dyes, including bromocresol green, fluorescein, and rhodamine 6G, show excellent catalytic activity under the irradiation of visible light, affording polyester products with predictable molecular mass and narrow dispersity (D < 1.10).
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| GB/T 7714 | Liu, Zhaogang , Zhang, Xun , Sun, Pan et al. Harnessing the photo-acidity of organic dyes for the development of ring-opening polymerization of lactones under visible light [J]. | POLYMER CHEMISTRY , 2023 , 14 (38) : 4414-4418 . |
| MLA | Liu, Zhaogang et al. "Harnessing the photo-acidity of organic dyes for the development of ring-opening polymerization of lactones under visible light" . | POLYMER CHEMISTRY 14 . 38 (2023) : 4414-4418 . |
| APA | Liu, Zhaogang , Zhang, Xun , Sun, Pan , Han, Junwei , Liao, Saihu . Harnessing the photo-acidity of organic dyes for the development of ring-opening polymerization of lactones under visible light . | POLYMER CHEMISTRY , 2023 , 14 (38) , 4414-4418 . |
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The incorporation of sulfonyl fluoride groups into molecules has been proven effective in enhancing their biological activities or introducing new functions. Herein, a transition-metal-free and visible-light-mediated radical tandem cyclization of unsaturated carboxylic acid is reported. This affords a facile access to FSO2-functionalized gamma-lac-tones efficiently, which are critical structural motifs widely present in biologically active molecules.
Keyword ：
cyclization cyclization difunctionlization difunctionlization FSO2 radical FSO2 radical gamma-lactone gamma-lactone photoredox photoredox
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| GB/T 7714 | Fang, Xin , Geng, Xuebing , Wang, Peng et al. FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones [J]. | SYNTHESIS-STUTTGART , 2023 , 56 (11) : 1727-1734 . |
| MLA | Fang, Xin et al. "FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones" . | SYNTHESIS-STUTTGART 56 . 11 (2023) : 1727-1734 . |
| APA | Fang, Xin , Geng, Xuebing , Wang, Peng , Zhang, Honghai , Liao, Saihu . FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones . | SYNTHESIS-STUTTGART , 2023 , 56 (11) , 1727-1734 . |
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