{"title":"Synthesis of 1,7-Annulated Indazole Derivatives via Bifunctional Brønsted Base Catalyzed Cascade Reaction","authors":"Pengcheng Shao, Weiwu Ren","doi":"10.1002/cjoc.70010","DOIUrl":"https://doi.org/10.1002/cjoc.70010","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel method for the asymmetric synthesis of 1,7-annulated indazoles has been developed via bifunctional Brønsted base catalyzed cascade reaction. This process enabled the formation of multiple chiral centers including a quaternary carbon center in high yields with excellent diastereoselectivities and enantioselectivities. The reaction exhibited broad functional group tolerance and mild reaction conditions.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 12","pages":"1373-1378"},"PeriodicalIF":5.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074396","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Nitrogen-Doped Engineering in Covalent Organic Frameworks for Photocatalytic Synthesis of Hydrogen Peroxide†","authors":"Wenbo Dong, Zhiying Qin, Xiangyang Liu, Longyu Li","doi":"10.1002/cjoc.70009","DOIUrl":"https://doi.org/10.1002/cjoc.70009","url":null,"abstract":"<div>\u0000 \u0000 <p>Photocatalytic synthesis of hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>) from air and water presents a sustainable and efficient alternative to the traditional anthraquinone method. Therefore, the design and synthesis of efficient photocatalysts for H<sub>2</sub>O<sub>2</sub> production are important. In this work, we apply a nitrogen-site engineering strategy to achieve high-performance photocatalysts by synthesizing three imine- linked oligo(phenylenevinylene)-based covalent organic frameworks (OPV-COFs) doped with different numbers of nitrogen atoms (denoted as COF-920-<i>n</i>N, <i>n</i> = 0, 1, 3). Comprehensive characterization confirmed the high crystallinity and porosity of the COFs, critical for efficient photocatalysis. Each OPV-COF exhibited the ability to rapidly synthesize H<sub>2</sub>O<sub>2</sub> using air and water, with COF-920-1N achieving the highest rate of 4288 μmol·g<sup>–1</sup>·h<sup>–1</sup> under visible light, higher than those of most of other reported COFs. Mechanism studies demonstrated that the introduction of pyridine nitrogen atoms at the junction changes the electronic structure and electron transfer path within the COFs, enhancing the photogenerated electron mobility and reducing the rate of electron-hole recombination. This study not only pioneers the class of OPV-COFs for photocatalytic synthesis of H<sub>2</sub>O<sub>2</sub>, but also sets a foundational strategy for the rational design of COFs in photocatalytic applications.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 13","pages":"1504-1512"},"PeriodicalIF":5.5,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144191218","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Pyridine-Based Rigidochromic Fluorescent Security Ink","authors":"Mengdi Zuo, Cong Zeng, Jie Liu, Huacan Wu, Shiyu Feng, Yu Dong, Weiguo Huang","doi":"10.1002/cjoc.70013","DOIUrl":"https://doi.org/10.1002/cjoc.70013","url":null,"abstract":"<div>\u0000 \u0000 <p>Traditional fluorescent probes typically display blueshifted emission in rigidifying media; however, a newly developed class of rigidochromic fluorophores derived from phenanthridine demonstrates remarkable redshifted emission under similar conditions. Pyridine, with similar N-heterostructure to those of phenanthridine group, is considered a promising candidate for achieving comparable rigidity-induced redshift behavior. In this work, we synthesized eight organic fluorophores featuring diverse functional units and substitutes by systematically combining pyridine with carbazole, triazatruxene (TAT), and tetraphenylethylene (TPE), respectively. These molecules exhibit significant emission redshifts (up to 225 nm, a record high value ever reported) or notable emission intensity changes as the rigidity of the polymer matrix increases, along with unique acid responsiveness. The differences in polar-π interactions between fluorophores and polymers diversify the emission behavior, advancing the development of secure printing and intelligent optical materials. By embedding these fluorophores into polymer films with helical phase structures, redshifted emission with tunable chirality was achieved. Notably, leveraging the acid-responsive properties of these fluorophores, a time-dependent light-controlled dynamic encryption system was constructed, successfully enabling multi-level information encryption. This research greatly expands the scope of rigidochromic fluorophores, and their applications in anti-counterfeiting and information storage.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 12","pages":"1405-1416"},"PeriodicalIF":5.5,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074451","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shichao Yang, Xiangwen Tan, Dan Liu, Huanfeng Jiang, Wanqing Wu
{"title":"Visible Light-Induced Arylation/Alkylation/Phosphorylation of Isocyanides via EDA Complex Activation","authors":"Shichao Yang, Xiangwen Tan, Dan Liu, Huanfeng Jiang, Wanqing Wu","doi":"10.1002/cjoc.70000","DOIUrl":"https://doi.org/10.1002/cjoc.70000","url":null,"abstract":"<div>\u0000 \u0000 <p>Herein, it is reported that the aryl radicals derived from aryl thianthrenium salts are used as coupling partner in the arylation reactions of isocyanides, simultaneously as initiators for the formation of alkyl and phosphoryl radicals from ethers and diarylphosphine oxides. This cascade cyclization reaction leads to diverse arylated, alkylated and phosphorylated heteroaromatic compounds. Notably, this transformation can be achieved without the aid of metals or photocatalysts, exhibiting a wide substrate applicability and operational simplicity. Mechanistic studies suggest the involvement of radical processes and electron donor-acceptor (EDA) complexes in this transformation.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 12","pages":"1379-1384"},"PeriodicalIF":5.5,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074732","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Chemoselective Csp2-H Radical Alkylation of Aryl Diazonium Salts with 1-Iodo-3-Pentafluorosulfanylbicyclo[1,1,1]pentane (SF5-BCP-I)†","authors":"Xin Zhao, Xin-Yu Li, Jia-Yi Shou, Feng-Ling Qing","doi":"10.1002/cjoc.70007","DOIUrl":"https://doi.org/10.1002/cjoc.70007","url":null,"abstract":"<div>\u0000 \u0000 <p>The reaction site of aryl diazonium salt was restricted in the position of diazonium moiety, due to the intrinsic electrophilicity of diazonium moiety. Herein, we described an unprecedented chemoselective alkylation of Csp<sup>2</sup>-H of aryl diazonium salts with 1-iodo-3-pentafluorosulfanylbicyclo[1,1,1]pentane (SF<sub>5</sub>-BCP-I). This novel alkylation of aryl diazonium salts provided an efficient access to various SF<sub>5</sub>-BCP substituted aromatics that might have great potential application in the drug discovery. Mechanistic experiments and theoretical studies revealed that the intrinsic electrophilic SF<sub>5</sub>-BCP radical resulted in the thermodynamic favorable radical addition on Csp<sup>2</sup>-H site rather than diazonium moiety of aryl diazonium salt.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 13","pages":"1523-1530"},"PeriodicalIF":5.5,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144191248","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xiaowei Wang, Jiayi Zhang, Jiajun Qu, Jun Li, Anchao Feng, Jun Liu
{"title":"Self-assembly Strategies Driven by Supramolecular RAFT Polymerization: Pseudorotaxanes and Nanosheets","authors":"Xiaowei Wang, Jiayi Zhang, Jiajun Qu, Jun Li, Anchao Feng, Jun Liu","doi":"10.1002/cjoc.70012","DOIUrl":"https://doi.org/10.1002/cjoc.70012","url":null,"abstract":"<div>\u0000 \u0000 <p>This study explores the use of supramolecular RAFT polymerization for the efficient synthesis of pseudorotaxanes and functional nanosheets through the host-guest interaction between β-cyclodextrin (β-CD) and the chain transfer agent (CTA) <i>S</i>,<i>S</i>’-bis(α,α’-dimethylacetic acid) trithiocarbonate (BDAAT). The formation of the β-CD@BDAAT complex significantly improves the water solubility of the CTA, thereby increasing the polymerization rate for <i>N</i>,<i>N</i>-dimethylacrylamide (DMA) and generating well-defined pseudorotaxane structure. In the process of aqueous polymerization-induced self-assembly (PISA), this supramolecular approach enables the rapid fabrication of functional nanosheets, reducing the required time from one week to just 5 h. The non-covalent support provided by β-CD is crucial for stabilizing the layered nanosheet assembly, while host-guest competition experiments also demonstrate the tunability of the morphology of non-covalently assembled structures. This study highlights the versatility of supramolecular RAFT polymerization, offering a promising strategy for the rapid and efficient production of complex nanostructures in aqueous media.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 13","pages":"1495-1503"},"PeriodicalIF":5.5,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144191247","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Photoresponsive Behavior of Triphenylamine-Based Organic Small Molecule Emitters Involving a Photo-Induced Charge-Transfer Complexation Mechanism under UV Light","authors":"Xu-Xu Jia, Yu-Xi Yuan, Qi Lin, Bingbing Shi, Hong Yao, Wen-Juan Qu, Tai-Bao Wei, Jin-Fa Chen","doi":"10.1002/cjoc.70005","DOIUrl":"https://doi.org/10.1002/cjoc.70005","url":null,"abstract":"<div>\u0000 \u0000 <p>Stimuli-responsive organic luminescent materials exhibit significant sensitivity to various external stimuli, among which their excellent photosensitivity is particularly prominent. This unique feature gives them great potential for applications. Herein, five organic small molecule emitters based on triphenylamine derivatives have been synthesized <i>via</i> Suzuki-coupling reaction. These small molecules have excellent fluorescence properties with fluorescence quantum yields (<i>Φ</i>) all reaching over 90%. When irradiated with a 365 nm UV lamp, interesting photochromic phenomena occurred in their chloroform solutions. This phenomenon has been studied intensively by UV-vis absorption and fluorescence spectroscopy, EPR measurements, and density functional theory calculations, and finally, the triphenylamine group was used as a photoinitiation precursor and electron donor, and the photo-induced charge transfer complex (PCTC) initiated by the donor molecule was successfully constructed.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 12","pages":"1385-1391"},"PeriodicalIF":5.5,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074733","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Pyrazino[2,3-f][1,10]phenanthroline Derivatives for Oxygen-Tolerant Dual Photoredox/Copper Catalyzed Atom Transfer Radical Polymerization with Ultra-low Catalyst Dosage","authors":"Wanchao Hu, Bei Liu, Shiyi Li, Changli Lü","doi":"10.1002/cjoc.70019","DOIUrl":"https://doi.org/10.1002/cjoc.70019","url":null,"abstract":"<div>\u0000 \u0000 <p>Substantial progress has been made over recent years in visible light-driven dual photoredox/copper catalyzed atom transfer radical polymerization (photo-ATRP) through the design of photocatalysts (PCs) and the optimization of reaction conditions. However, it remains challenging to achieve efficient photo-ATRP with low loadings of both photocatalyst and copper(II). In this study, two donor-acceptor organic PCs based on pyrazino[2,3-<i>f</i>][1,10]phenanthroline were successfully used to achieve efficient Cu(II)-mediated photo-ATRP. These organic PCs exhibit excellent visible light absorption capabilities and thermally activated delayed fluorescence (TADF) properties. Under blue light irradiation, the PCs facilitated highly efficient and oxygen-tolerant polymerization with an extremely low catalyst loading (50 ppb). This system demonstrated a broad applicability to various monomers, achieving successful polymerization of methacrylates, acrylates, and styrene. Additionally, efficient photo-ATRP on a large scale (250 mL) was achieved, resulting in narrow molecular weight polymers with high monomer conversions and high chain-end fidelity. This work provides an in-depth investigation into the regulatory process of photo-ATRP, offering new insights into the intricate mechanism of oxygen tolerance.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 11","pages":"1315-1324"},"PeriodicalIF":5.5,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897089","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yu Liu, Yingquan Yang, Yuchao Zhang, Jie Yi, Liqi Wan, Yang Wang, Qian Gao, Dong Xu, Pei Guo, Da Han
{"title":"Structural Basis for the GGGGCC Repeat RNA Binding to SRSF2 Protein†","authors":"Yu Liu, Yingquan Yang, Yuchao Zhang, Jie Yi, Liqi Wan, Yang Wang, Qian Gao, Dong Xu, Pei Guo, Da Han","doi":"10.1002/cjoc.70004","DOIUrl":"https://doi.org/10.1002/cjoc.70004","url":null,"abstract":"<p><b>Comprehensive Summary</b></p><p>RNA-protein interactions are crucial for regulating various cellular processes such as gene expression, RNA modification and translation. In contrast, undesirable RNA-protein interactions often cause dysregulated cellular activities associated with many human diseases. The RNA containing expanded GGGGCC repeats forms secondary structures that sequester various RNA binding proteins (RBPs), leading to the development of amyotrophic lateral sclerosis (ALS) and frontotemporal dementia (FTD). However, a gap persists in understanding the structural basis for GGGGCC repeat RNA binding to RBPs. Here, we resolve the first solution NMR structure of a natural GGGGCC repeat RNA containing a 2 × 2 GG/GG internal loop, and perform MD simulations and site-directed mutagenesis to elucidate the mechanism for GGGGCC repeat RNA binding to SRSF2, a splicing factor and key marker of nuclear speckles. We reveal that the R47/T51/R61 residues in RNA recognition motif of SRSF2 and the 2 × 2 GG/GG internal loop in GGGGCC repeat RNA are essential for binding. This work furnishes a valuable high-resolution structural basis for understanding the binding mechanism for GGGGCC repeat RNA and RBPs, and steers RNA structure-based drug design.</p><p>\u0000 </p>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 12","pages":"1348-1356"},"PeriodicalIF":5.5,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074530","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Multi-arm Branched Poly(carbazole-aryl piperidinium) Anion Exchange Membrane with High Conductivity and Good Alkaline Stability for Fuel Cells","authors":"Hui Zhang, Qiong Xiang, Xuedong Zhang, Wei Yuan, Li Li, Jianchuan Wang, Zidong Wei","doi":"10.1002/cjoc.202500023","DOIUrl":"https://doi.org/10.1002/cjoc.202500023","url":null,"abstract":"<div>\u0000 \u0000 <p>The lack of anion exchange membranes (AEMs) with good conductivity and alkaline stability has been one of the challenges for alkaline fuel cells. Introducing branched structure was a good strategy to promote conductivity and alkaline stability due to the bigger free volume of polymer and steric hindrance of cation. Herein, a series of branched AEMs with multiple arms (four and six) were successfully prepared. Multi-arm branched AEMs demonstrated obvious improvement of conductivity and alkaline stability because of the larger free volume and steric hindrance of multi-arm branched structures, respectively. Four-arm branched B4-QPPCTP-5 exhibited best comprehensive performance, including high conductivity of 242.2 mS·cm<sup>–1</sup>, a good alkaline stability of 2000 h with hardly degradation, and high mechanical property of >40 MPa. Single fuel cell based on multi-arm branched AEMs exhibited high power output of 1.2 W·cm<sup>–2</sup>. This work provides effective theoretical guidance for polymer structure design and preparation of branched AEMs.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 12","pages":"1357-1362"},"PeriodicalIF":5.5,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}