Yaxin Wang, Yuan Yuan, Shuaipeng Zhang, Long Chen, Yulan Chen
{"title":"Cholesterol Decorated Diazocine Gelator with Photo- and Thermo-Responsive Properties for Smart Window","authors":"Yaxin Wang, Yuan Yuan, Shuaipeng Zhang, Long Chen, Yulan Chen","doi":"10.1002/cjoc.202400527","DOIUrl":"10.1002/cjoc.202400527","url":null,"abstract":"<div>\u0000 \u0000 <p>A new gelator (<b>BAzo-Chol</b>) comprising a diazocine core and two cholesterol units linked via carbamate groups has been designed and synthesized. Its gelation ability in several kinds of organic solvents is identified. Investigations with scanning electron microscopy (SEM), transmission electron microscopy (TEM), rheological measurements, and UV<b>-</b>vis absorption and <sup>1</sup>H NMR spectroscopy reveal that <b>BAzo-Chol</b> can self-assemble into elastically interpenetrating one-dimensional nanostructures in organogels through a cooperative effect of the π-π interactions, hydrogen-bonding, and van der Waals forces. Moreover, the unconventional <i>Z</i>/<i>E</i> conformational transitions of these organogels, due to the inclusion of diazocine, endow the <b>BAzo-Chol</b> gels with excellent photo-responsive gel-sol transition and remarkable visible light-induced chromic properties. Lastly, due to its sensitive response to visible light accompanied by distinct changes in both colour and transparency of the gel-sol transitions, the potential application of the current gelator in smart windows is signified.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3278-3282"},"PeriodicalIF":5.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195516","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":"Hyperkouytones A—O, New Polyprenylated Acylphloroglucinols from Hypericum kouytchense with Multidrug Resistance Reversal Activity","authors":"Hua-Yong Lou, Mei-Jun Chen, Ping Yi, Jun Jin, Yan-Rong Zeng, Wei Gu, Zhan-Xing Hu, Jue Yang, Xiao-Jiang Hao, Chun-Mao Yuan","doi":"10.1002/cjoc.202400739","DOIUrl":"10.1002/cjoc.202400739","url":null,"abstract":"<div>\u0000 \u0000 <p>Given the lack of systematic polyprenylated acylphloroglucinols (PPAPs) research on traditional Chinese medicine of <i>Hypericum kouytchense</i>, this plant was applied for the phytochemical study, which led to fifteen new PPAPs (<b>1</b>—<b>15</b>, PPAPs), along with 36 known PPAP derivatives. Their structures and absolute configurations were established by comprehensive spectral analysis and theoretical ECD and NMR calculations. Structurally, compound <b>1</b> possesses a rare fused 6/6/6/5/5 pentacyclic ring system. Eleven compounds exhibited good multidrug resistance reversal activity (RF ranging from 5 to 53) in HepG2/ADR cells. Importantly, compound <b>34</b>, the most potential MDR modulator, showed better reversal effect (RF: 53) than positive control, verapamil. The primary mechanistic study of compound <b>34</b>, implied that this compound could prohibit the function of P-gp transport rather than its expression. The possible recognition mechanism between compound <b>34</b> and P-gp was predicted by molecular docking.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3293-3307"},"PeriodicalIF":5.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195515","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}
Min Liu, Qihuan Han, Lan Wang, Xi Chen, Xue Zhang, Hongchao Guo
{"title":"Amide-Based Morita–Baylis–Hillman Carbonates for Phosphine-Catalyzed Asymmetric (4+2) Annulation†","authors":"Min Liu, Qihuan Han, Lan Wang, Xi Chen, Xue Zhang, Hongchao Guo","doi":"10.1002/cjoc.202400657","DOIUrl":"10.1002/cjoc.202400657","url":null,"abstract":"<div>\u0000 \u0000 <p>Chiral phosphine-catalyzed asymmetric (4+2) annulation of the amide-based Morita–Baylis–Hillman (MBH) carbonates with β,γ-unsaturated butenolides has been developed to give enantiomer-enriched bicyclic δ-lactam γ-butyrolactone compounds. The amide-based MBH carbonates were first used as acceptor and aza-C4 synthon in phosphine catalysis. Under mild reaction conditions, a variety of amide-based MBH carbonates and unsaturated butenolides were well tolerated to provide chiral bicyclic δ-lactam γ-butyrolactone derivatives in high yields with excellent enantioselectivities as well as diastereoselectivities. A plausible reaction mechanism was also proposed based on control experiments and DFT calculations.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3269-3277"},"PeriodicalIF":5.5,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195528","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}
Chun-Lan Xie, Tai-Zong Wu, Duo Zhang, Yuan Wang, Ting Lin, Hai-Feng Chen, Xiao-Kun Zhang, Xian-Wen Yang
{"title":"Unveiling the Mechanisms of Apoptosis Induction by Deep-Sea-Derived Polyketide-Terpenoid Hybrids from Penicillium allii-sativi: A Focus on Mitochondrial and mTOR Pathways","authors":"Chun-Lan Xie, Tai-Zong Wu, Duo Zhang, Yuan Wang, Ting Lin, Hai-Feng Chen, Xiao-Kun Zhang, Xian-Wen Yang","doi":"10.1002/cjoc.202400752","DOIUrl":"10.1002/cjoc.202400752","url":null,"abstract":"<div>\u0000 \u0000 <p>A chemical investigation of the deep-sea-derived fungus <i>Penicillium allii-sativi</i> MCCC 3A00580 resulted in the discovery of four new meroterpenoids (<b>1</b>—<b>4</b>) and one related known co-metabolite (<b>5</b>). These meroterpenoids showcase unique carbon skeletons featuring a common drimane sesquiterpene part with highly diverse polyketide units. Particularly, compound <b>1</b> incorporates a salicylic acid moiety while <b>2</b> possesses a rare peroxide bridge in the polyketide part. The structures of new compounds were assigned by extensive spectroscopic analysis, quantum calculations, and biogenetic considerations. Notably, <b>3</b> significantly blocked the mTOR signaling pathway, resulting in the arrest of cell cycle at G0-G1 phase and triggering mitochondrial apoptosis in Hela cells. While the previously reported co-metabolite macrophorin A (MPA) effectively triggered cell death in MDA-MB-231 cancer cells by activating apoptosis pathways involving death receptors, mitochondria, mTOR, and TNF.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3283-3292"},"PeriodicalIF":5.5,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195518","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":"Synthetic Investigation toward Acyl Group-Free Escin Derivatives","authors":"Xin Lv, Jin-Xi Liao, Zhen-Qiang Li, Zhi-Sheng Xiong, Qi-Shuang Yin, Hui Liu, Yuan-Hong Tu, Jian-Song Sun","doi":"10.1002/cjoc.202400778","DOIUrl":"10.1002/cjoc.202400778","url":null,"abstract":"<div>\u0000 \u0000 <p>With protoescigenin as starting material and through orchestrated application of Yu and Schmidt glycosylation protocols, the synthesis of acyl group-free escin derivatives was achieved for the first time. As the undesired non-specific toxicity, originating from the existence of acyl groups on aglycone, prohibits the wide application of escins, the established strategies toward non-acylated protoescigenin-type saponins would dramatically ease the access to escin derivatives dispense of acyl groups, thereby speeding up the pace of pharmaceutical use of these valuable compounds.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3263-3268"},"PeriodicalIF":5.5,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195519","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}
Panqi Sun, Chenggong Yang, Fei Peng, Junbo Dang, Wentao Wang, Daiwu Deng, Ning-Ning Zhang, Yang Yang, Kun Liu
{"title":"Free-Radical Polymerization Induced Grafting-to of Polymer Chains onto Aluminum Nanoparticles†","authors":"Panqi Sun, Chenggong Yang, Fei Peng, Junbo Dang, Wentao Wang, Daiwu Deng, Ning-Ning Zhang, Yang Yang, Kun Liu","doi":"10.1002/cjoc.202400510","DOIUrl":"10.1002/cjoc.202400510","url":null,"abstract":"<div>\u0000 \u0000 <p>Aluminum nanoparticles (Al NPs) have significant potential applications in various fields due to their unique LSPR. Significant advancements have been achieved in controlling the size and morphology of Al NPs. However, the efficient modification of Al NPs with polymers has not been implemented. Herein, we report a facile and efficient free-radical polymerization induced grafting-to (FRPIGt) method for grafting polymer chains onto Al NPs. By optimizing polymerization conditions, we were able to achieve a polymer brush layer with a weight loss fraction of up to 43.3%, which was higher than those of other polymers with carboxyl or primary amine end groups. Moreover, a broad range of vinyl monomers, including styrene, methacrylate, and methyl methacrylate, can be applied using the FRPIGt method to modify Al NPs. In addition, the FRPIGt method can be extended to photoinduced organocatalyzed atom-transfer-radical polymerization. This work paves a new path for the preparation of a wide range of polymer-functionalized Al NPs and their polymer composites to be utilized in various fields.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3193-3200"},"PeriodicalIF":5.5,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195517","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}
Xu Wang, Jing Tian, Zuhao You, Le Lei, Aokang Ge, Yao Liu
{"title":"Electroactive and Self-healing Polyurethane Doped Tin Oxide Interlayers for Efficient Organic Solar Cells†","authors":"Xu Wang, Jing Tian, Zuhao You, Le Lei, Aokang Ge, Yao Liu","doi":"10.1002/cjoc.202400692","DOIUrl":"10.1002/cjoc.202400692","url":null,"abstract":"<div>\u0000 \u0000 <p>Tin oxide (SnO<sub>2</sub>) has been widely used as an electron transport layer (ETL) in optoelectronic devices. However, there are numerous surface or bulk defects in SnO<sub>2</sub>, working as charge recombination centers to degrade device. Here, an electroactive and self-healing polyurethane (PHNN) was designed by integrating conjugated unit – naphthalene diimide (NDI) into a typical polyurethane backbone. Numerous hydrogen bonds and π interactions in PHNN work as non-covalent interactions to endow this polymer with superior self-healing properties. PHNN contains lots of aliphatic amine and carbonyl groups, which effectively passivate the defects in SnO<sub>2</sub>. The π stacking of NDI units will facilitate electron delocalization, endowing PHNN with electrical activity compared with traditional polyurethane. Doping SnO<sub>2</sub> with PHNN can improve the conductivity and reduce the work function of SnO<sub>2</sub> layer, which is conducive to efficient charge extraction and transport. Using PHNN doped SnO<sub>2</sub> as ETL for PM6: Y6 and PM6: BTP-eC9 based inverted organic solar cells can achieve a high efficiency of 17.16% and 17.51%, respectively. Devices containing doped SnO<sub>2</sub> ETL show significantly improved efficiency and stability. Thus, the electroactive polyurethane doped SnO<sub>2</sub> interlayers show high performance interfacial modification to align energy-levels in solar cell devices, which have promising applications in organic electronics.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"2979-2986"},"PeriodicalIF":5.5,"publicationDate":"2024-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195522","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}
Kai Zhu, Jiping Xiao, Yingying Bi, Mingjun Nie, Lin Ai, Xun Feng, Siyu Lu
{"title":"Rational Design of Multi-color Phosphorescent Carbon Dots Based on Binaphthyldiamine with Chiral Signals","authors":"Kai Zhu, Jiping Xiao, Yingying Bi, Mingjun Nie, Lin Ai, Xun Feng, Siyu Lu","doi":"10.1002/cjoc.202400546","DOIUrl":"10.1002/cjoc.202400546","url":null,"abstract":"<div>\u0000 \u0000 <p>Chiral phosphorescent materials have received extensive research owing to the unique properties of optical activity in recent years. Many phosphorescent carbon dots (CDs) materials have been reported, but the research on chiral phosphorescence is still in the exploratory stage. This work designs multi-color room temperature phosphorescent (RTP) CDs with chiral signals, which are fully mixed with aromatic aldehyde precursors and chiral amino compounds precursors in a boric acid (BA) matrix and can be easily prepared by solvent-free thermal method. The prepared (<i>R</i>)-GCDs, (<i>R</i>)-YCDs and (<i>R</i>)-RCDs achieved phosphorescence emission at 545 nm, 582 nm, and 654 nm, respectively, and exhibited corresponding circular dichroism (CD) signals at 341 nm, 394 nm, 384 nm, and 380 nm, 448 nm, and 435 nm, respectively. The longest phosphorescence lifetime is up to 946 ms. Specifically, YCDs exhibit time-dependent phosphorescence under UV excitation, and the afterglow time under white light excitation can reach 40 s. This article provides a new approach to the study of chiral phosphorescence.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3255-3262"},"PeriodicalIF":5.5,"publicationDate":"2024-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195520","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":"Cobalt-Catalyzed Regioselective Methylative Coupling of Internal Alkynes with Aldehydes/Aldimines","authors":"Jiwu Zhang, Zhikun Liang, Qinglei Chong, Fanke Meng","doi":"10.1002/cjoc.202400641","DOIUrl":"10.1002/cjoc.202400641","url":null,"abstract":"<div>\u0000 \u0000 <p>Catalytic methylative coupling of internal alkynes and aldehydes/aldimines through regioselective oxidative cyclization promoted by a phosphine–Co complex is presented. Such process constitutes an unprecedented and unique approach for Co-catalyzed generation of metallacycles that reversed inherent regiochemical biases to furnish a wide range of allylic alcohols and allylic amides bearing a tetrasubstituted alkene in up to 98% yield with high regioselectivity, representing a novel and general strategy for reversal of substrate-controlled regioselectivity in metal-catalyzed oxidative cyclization.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3248-3254"},"PeriodicalIF":5.5,"publicationDate":"2024-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142225162","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":"Visible Light-Promoted Aerobic Oxidation of α-Silyl Styrenes with Alcohols","authors":"Yan Tan, Bo Yang, Jiale Ying, Bing Yu, Zhan Lu","doi":"10.1002/cjoc.202400602","DOIUrl":"10.1002/cjoc.202400602","url":null,"abstract":"<div>\u0000 \u0000 <p>A mechanistically distinctive visible-light-promoted metal-free aerobic oxidation of alkenyl silanes with alcohols was disclosed to efficiently construct <i>α</i>-alkoxy ketones under mild conditions. The primary, secondary, and tertiary alcohols could be used as reactants. The protocol could be carried out on a gram-scale. Various derivatizations of products could be conducted. Mechanistic studies indicated the reaction was initiated by single-electron oxidation of the alkenyl silanes, rather than radical addition to alkenyl silanes.</p>\u0000 <p></p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 24","pages":"3243-3247"},"PeriodicalIF":5.5,"publicationDate":"2024-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195521","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}