Shuixiu Su, Ying Chen, Qiyu Wang, Jian Zhang, Yang-Zi Liu, Wei-Ping Deng
{"title":"Enantioselective Construction of Spirooxindole-γ-butyrolactones via NHC-Bound Isobenzofulvene [10π+2π] Cycloaddition","authors":"Shuixiu Su, Ying Chen, Qiyu Wang, Jian Zhang, Yang-Zi Liu, Wei-Ping Deng","doi":"10.1002/cjoc.70071","DOIUrl":"https://doi.org/10.1002/cjoc.70071","url":null,"abstract":"<div>\u0000 \u0000 <p>We report an <i>N</i>-heterocyclic carbene (NHC)-catalyzed [10π+2π] cycloaddition between indene-2-carbaldehydes and isatins, delivering spirooxindole-γ-butyrolactones with moderate yields (up to 68%) and excellent enantioselectivity (up to 93% ee). This transformation proceeds via NHC-bound isobenzofulvene intermediates and represents the first successful application of all-carbon higherene in NHC-catalyzed [10π+2π] cycloadditions.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1983-1987"},"PeriodicalIF":5.5,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144624226","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":"Photoinduced Ring-Opening Functionalization of α-Imino-Oxy Acids and Alkanols Enabled by Phthalate-Derived Proton-Coupled Electron Transfer Mediator","authors":"Chao Tian, Lei Shi","doi":"10.1002/cjoc.70074","DOIUrl":"https://doi.org/10.1002/cjoc.70074","url":null,"abstract":"<div>\u0000 \u0000 <p>A dual catalytic manifold that combines photoredox catalysis and phthalate-catalyzed hydrogen-atom abstraction process has been developed to realize diverse fragmentation-functionalization reactions. Key to success is photocatalytic generation of tether-tunable distonic radical anions (TDRAs) as proton-coupled electron transfer mediators, enabling polarity-matching-based formation of heteroatom-centered radicals that allows for further controlled exploration of chemical space via C–C <i>β</i>-scission. These reactions feature exceptionally broad substrate generality, gram-scale synthesis, potential biocompatibility and late-stage modification of complex molecules, while obviating the use of stoichiometric and often unsafe peroxides in our previous studies. Mechanistic studies support a redox-neutral radical relay pathway enabled by <i>in situ</i>-generated, catalytic TDRAs.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1988-1996"},"PeriodicalIF":5.5,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144624286","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":"Interfacial Microenvironment Engineering Based on Ordered TiO2 Porous Films for Enhanced Visible Light Driven Photocatalysis","authors":"ZhaoYue Tan, Xi Chen, Zhiping Liu, JingYu Lu, Xia Sheng, Xinjian Feng","doi":"10.1002/cjoc.70069","DOIUrl":"https://doi.org/10.1002/cjoc.70069","url":null,"abstract":"<div>\u0000 \u0000 <p>Visible-light-driven photocatalysis has great potential in environmental remediation and organic synthesis. Rational design and regulation of the reaction interfacial microenvironment is critical for photocatalytic performance, yet challenging. We report here a highly efficient photocatalytic system based on hydrophobic TiO<sub>2</sub> porous (H-OTP) film for visible-light-driven dye-sensitized photo-oxidation. Such interface architecture design enhances the adsorption capability of organic dyes and enables the formation of air trapped triphase reaction interface microenvironment as confirmed via three-dimensional (3D) laser scanning confocal microscopy. Based on this interface architecture, the concentrations of O<sub>2</sub> and organic molecule at the local reaction zone are both significantly increased, which promotes the generation of reactive oxygen species (•O<sub>2</sub><sup>−</sup> and •OH), and enhances the photocatalytic performance in terms of both kinetics and organic mineralization efficiency. This study highlights the importance of interface microenvironment design and reveals an effective way to develop highly efficient photocatalytic systems.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1961-1967"},"PeriodicalIF":5.5,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144624273","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}
Pan Qi, Xiaobing Li, Houguo Fei, Zijie Wang, Cunlan Guo
{"title":"Structural Factors Tuning Peptide Proton Transport via Self-Assembly Monolayers","authors":"Pan Qi, Xiaobing Li, Houguo Fei, Zijie Wang, Cunlan Guo","doi":"10.1002/cjoc.70067","DOIUrl":"https://doi.org/10.1002/cjoc.70067","url":null,"abstract":"<div>\u0000 \u0000 <p>Proton transport (PT) in solid-state materials is crucial for applications in energy conversion and protonic devices. Nevertheless, the highly complex and disordered structures of conventional proton-conducting materials, such as polymers and proteins, hinder a clear understanding of the mechanisms underlying PT, particularly the formation of hydrogen bond (H-bond) networks and their role in mediating PT. Here, we show that self-assembling monolayers (SAMs) of oligopeptides provide a promising platform for elucidating the key factors that modulate PT related H-bonds, including amide bond interactions, peptide sequence, and chain length. Combined with structural characterizations of SAMs, the electrical measurements under both direct and alternating current modes demonstrate that longer and more extended oligopeptide chains in SAMs result in an ordered molecular arrangement, leading to a more pronounced response of current density (<i>J</i>) to increasing relative humidity (RH). Moreover, this increase in molecular order also shifts the transition from electron-dominated to proton-dominated charge transport to a higher RH. The synergy between carrier concentration and mobility is a key factor contributing to the increase in <i>J</i>. This study not only elucidates the critical role of ordered H-bonds in PT but also expands the application of SAM technology in controlling molecular conformation and enhancing proton conduction.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1924-1930"},"PeriodicalIF":5.5,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144624716","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}
Ren-Jie Yu, Rui-Rui Zhao, Fang Hu, Zhen Su, Ke Gao, Liang-Qiu Lu, Wen-Jing Xiao
{"title":"Heterogeneous Organic Polymers Embedded with Chiral Bisoxazoline Ligands for Photoinduced Cu-Catalyzed Asymmetric Cyanation","authors":"Ren-Jie Yu, Rui-Rui Zhao, Fang Hu, Zhen Su, Ke Gao, Liang-Qiu Lu, Wen-Jing Xiao","doi":"10.1002/cjoc.70052","DOIUrl":"https://doi.org/10.1002/cjoc.70052","url":null,"abstract":"<div>\u0000 \u0000 <p>Chiral bisoxazoline (box) ligands with indene groups at C4 and C5 are highly potent in asymmetric catalysis, but face challenges in terms of cost and recyclability. To address this, we have designed polystyrene-supported box ligands by modifying the indene moiety instead of the traditional methylene bridge. This design preserves the necessary steric environment for copper coordination, enabling high efficiency and excellent enantioselectivity as examined in photoinduced asymmetric cyanation reactions. The resulting copper complexes are robust and recyclable, maintaining performance over five cycles. This approach provides a sustainable and practical solution for asymmetric catalysis with chiral box ligands.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1931-1937"},"PeriodicalIF":5.5,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144624225","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}
Ke Li, Shiliang Zhu, Ying Peng, Ling Qiu, Jianguo Lin
{"title":"A Self-immobilizing PET Tracer for Imaging of H2O2 Level \u0000in the Brain","authors":"Ke Li, Shiliang Zhu, Ying Peng, Ling Qiu, Jianguo Lin","doi":"10.1002/cjoc.70059","DOIUrl":"https://doi.org/10.1002/cjoc.70059","url":null,"abstract":"<div>\u0000 \u0000 <p>Reactive oxygen species (ROS) are involved in the onset and development of neurodegenerative diseases, such as Alzheimer's disease (AD) and Parkinson's disease (PD). Hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>), a key type of ROS, is overexpressed in the early stages of AD and PD and is involved in the disease progression. Assessing H<sub>2</sub>O<sub>2</sub> levels in the brain is considered to be a valuable tool for detecting neurodegenerative diseases and exploring their pathogenesis. In this study, we developed two self-immobilizing PET tracers (<b>[</b><sup><b>18</b></sup><b>F]HYAS</b> and <b>[</b><sup><b>18</b></sup><b>F]HYAT</b>) based on a quinone methide (QM) scaffold for non-invasive imaging of H<sub>2</sub>O<sub>2</sub> in the brain. Both tracers can respond to H<sub>2</sub>O<sub>2</sub> by forming a QM intermediate, which rapidly reacts with nucleophiles. <b>[</b><sup><b>18</b></sup><b>F]HYAT</b>, with proper physicochemical properties, is able of crossing the blood-brain barrier. Increased uptake of <b>[</b><sup><b>18</b></sup><b>F]HYAT</b> was observed in the brains of mice treated with 1-methyl-4-phenyl- l,2,3,6-tetrahydropyridine (MPTP), indicating that <b>[</b><sup><b>18</b></sup><b>F]HYAT</b> is a useful tracer for PET imaging of H<sub>2</sub>O<sub>2</sub> in the brain.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1938-1944"},"PeriodicalIF":5.5,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144624198","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}