Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou
{"title":"Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion","authors":"Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou","doi":"10.1016/j.cclet.2024.110174","DOIUrl":"10.1016/j.cclet.2024.110174","url":null,"abstract":"<div><div>Diradicaloid polycyclic hydrocarbons (PHs) own unique open-shell electronic structures and exhibit potential utility in the fields of organic electronics and spintronics. Herein, we disclose precise fusion of B/O-heterocycles onto PHs for control over their electronic structures and diradical properties. We designed and synthesized four B/O-containing diradicaloid isomers that feature the fluoreno[3,2-<em>b</em>]fluorene and fluoreno[2,1-<em>a</em>]fluorene <em>π</em>-skeletons, respectively. The precise B/O-heterocycle fusion modes along with the changed conjugation patterns lead to their modulated electronic structures and properties, such as diradical and aromatic structures, energy levels and band gaps, as well as magnetic, electrochemical and photophysical properties. Notably, the mode A may decrease the open-shell extent, whereas the mode B can enhance the diradical nature, leading to their well-tuned diradical characters in the range of 0.46‒0.70. Moreover, the mode A stabilizes the LUMOs and the mode B obviously increases the HOMO levels, which are remarkably contributed by the B and O atoms, respectively, further giving rise to the decreased band gaps and redshifted absorptions. This study clearly illustrates the electronic effects of B/O-heterocycle fusion on PHs and gains insight into B/O-type organic diradicaloids. These findings will provide an important guideline for the design of more fascinating heteroatom-containing diradicaloids.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 1","pages":"Article 110174"},"PeriodicalIF":9.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142552832","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}
Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma
{"title":"Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine","authors":"Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma","doi":"10.1016/j.cclet.2024.109791","DOIUrl":"10.1016/j.cclet.2024.109791","url":null,"abstract":"<div><p>Reported here is the synthesis of a new macrocycle bearing anionic carboxylate groups with water-soluble aggregation-induced emission (AIE). The water-soluble macrocycle without typical AIE luminogens is constructed based on the building block of benzothiadiazole. It exhibits a remarkable AIE effect. This water-soluble macrocycle can selectively bind different types of biogenic amines in aqueous media with the tightest binding towards spermine. The fluorescence enhancement induced by supramolecular encapsulation is used to detect spermine.</p></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"35 11","pages":"Article 109791"},"PeriodicalIF":9.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141954566","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}
Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi
{"title":"Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones","authors":"Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi","doi":"10.1016/j.cclet.2024.110112","DOIUrl":"10.1016/j.cclet.2024.110112","url":null,"abstract":"<div><p>A facile visible-light-induced 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) catalyzed four-component reaction of alkenes, quinoxalin-2(1<em>H</em>)-ones, P<sub>4</sub>S<sub>10</sub> and alcohols has been developed at room temperature. This tandem reaction provides an efficient strategy for the construction of various phosphorodithioate-containing quinoxalin-2(1<em>H</em>)-ones with moderate to good yields by using air (dioxygen) as the green oxidant. Experimental studies revealed a radical process was involved in this photochemical reaction.</p></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"35 11","pages":"Article 110112"},"PeriodicalIF":9.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141954567","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}
Qinghong Pan , Huafang Zhang , Qiaoling Liu , Donghong Huang , Da-Peng Yang , Tianjia Jiang , Shuyang Sun , Xiangrong Chen
{"title":"A self-powered cathodic molecular imprinting ultrasensitive photoelectrochemical tetracycline sensor via ZnO/C photoanode signal amplification","authors":"Qinghong Pan , Huafang Zhang , Qiaoling Liu , Donghong Huang , Da-Peng Yang , Tianjia Jiang , Shuyang Sun , Xiangrong Chen","doi":"10.1016/j.cclet.2024.110169","DOIUrl":"10.1016/j.cclet.2024.110169","url":null,"abstract":"<div><div>Quantitative determination of tetracycline (TC) in environment and foods is of great importance, as excessive residues might have negative effects on human health and environmental risks. Herein, a self-powered molecularly imprinted photoelectrochemical (PEC) sensor based on the ZnO/C photoanode and the Fe-doped CuBi<sub>2</sub>O<sub>4</sub> (CBFO) photocathode is developed for the sensitive detection of TC. The photocathodic current can be amplified by the efficient electron transfer caused by the Fermi energy level gap between the photoanode and photocathode. Furthermore, molecularly imprinted polymers (MIPs) at photocathode can selectivity identify the TC templates and thus improve the specificity. Under the optimal conditions, the sensor has a linear range of 10<sup>‒2</sup>–1.0 × 10<sup>5</sup> nmol/L, and a limit of detection (LOD) of 0.007 nmol/L (S/N = 3). More crucially, the milk sample detection is carried out using the as-prepared sensor, and the outcome is satisfactory. The research gives us a novel sensing platform for quick and accurate antibiotic (like TC) in environment and food monitoring.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 1","pages":"Article 110169"},"PeriodicalIF":9.4,"publicationDate":"2024-06-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592840","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}
Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao
{"title":"Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer","authors":"Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao","doi":"10.1016/j.cclet.2024.110167","DOIUrl":"10.1016/j.cclet.2024.110167","url":null,"abstract":"<div><div>Pyridyl-based ketones and 1,6-diketones are both attractive and invaluable scaffolds which play pivotal roles in the construction and structural modification of a plethora of synthetically paramount natural products, pharmaceuticals, organic materials and fine chemicals. In this context, we herein demonstrate an unprecedented, robust and generally applicable synthetically strategy to deliver these two crucial ketone frameworks <em>via</em> visible-light-induced ring-opening coupling reactions of cycloalcohols with vinylazaarenes and enones, respectively. A plausible mechanism involves the selective <em>β</em>-C-C bond cleavage of cycloalcohols enabled by proton-coupled electron transfer and ensuing Giese-type addition followed by single electron reduction and protonation. The synthetic methodology exhibits broad substrate scope, excellent functional group compatibility as well as operational simplicity and environmental friendliness.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 2","pages":"Article 110167"},"PeriodicalIF":9.4,"publicationDate":"2024-06-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657005","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 Xiong, Li-Jun Hu, Jian-Guo Song, Di Zhang, Yi-Shuang Peng, Xiao-Jun Huang, Jian Hong, Bin Zhu, Wen-Cai Ye, Ying Wang
{"title":"Structure elucidation of plumerubradins A–C: Correlations between 1H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives","authors":"Yu Xiong, Li-Jun Hu, Jian-Guo Song, Di Zhang, Yi-Shuang Peng, Xiao-Jun Huang, Jian Hong, Bin Zhu, Wen-Cai Ye, Ying Wang","doi":"10.1016/j.cclet.2024.110149","DOIUrl":"https://doi.org/10.1016/j.cclet.2024.110149","url":null,"abstract":"[2+2]-Type cyclobutane derivatives comprise a large family of natural products with diverse molecular architectures. However, the structure elucidation of the cyclobutane ring, including its connection mode and stereochemistry, presents a significant challenge. Plumerubradins A–C (–), three novel iridoid glycoside [2+2] dimers featuring a highly functionalized cyclobutane core and multiple stereogenic centers, were isolated from the flowers of Plumeria rubra. Through biomimetic semisynthesis and chemical degradation of compounds –, synthesis of phenylpropanoid-derived [2+2] dimers –, combined with extensive spectroscopic analysis, single-crystal X-ray crystallography, and microcrystal electron diffraction experiments, the structures with absolute configurations of – were unequivocally elucidated. Furthermore, quantum mechanics-based H NMR iterative full spin analysis successfully established the correlations between the signal patterns of cyclobutane protons and the structural information of the cyclobutane ring in phenylpropanoid-derived [2+2] dimers, providing a diagnostic tool for the rapid structural elucidation of [2+2]-type cyclobutane derivatives.","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"539 1","pages":""},"PeriodicalIF":9.1,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141529545","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}
Shenglan Zhou , Haijian Li , Hongyi Gao , Ang Li , Tian Li , Shanshan Cheng , Jingjing Wang , Jitti Kasemchainan , Jianhua Yi , Fengqi Zhao , Wengang Qu
{"title":"Recent advances in metal-loaded MOFs photocatalysts: From single atom, cluster to nanoparticle","authors":"Shenglan Zhou , Haijian Li , Hongyi Gao , Ang Li , Tian Li , Shanshan Cheng , Jingjing Wang , Jitti Kasemchainan , Jianhua Yi , Fengqi Zhao , Wengang Qu","doi":"10.1016/j.cclet.2024.110142","DOIUrl":"10.1016/j.cclet.2024.110142","url":null,"abstract":"<div><div>Photocatalysis is widely regarded as a highly promising sustainable technique for addressing the challenges posed by environmental pollution and energy provision. In recent years, metal-loaded MOFs has become a rising star within the domain of photocatalysis due to its high specific surface area and porosity, adjustable structure, diverse and abundant catalytic components, which has exhibited excellent photocatalytic activity and exhibit great potential in a range of disciplines. In this paper, the principles for evaluating the photocatalytic performance of MOFs-based materials were firstly introduced, and some typical examples were also listed accordingly. Along with this, particular emphasis is paid to the main factors affecting the photocatalytic performance of metal-loaded MOFs. Then the synthesis and design strategies of MOFs loaded metal entities of varying sizes (single atoms, nanoclusters, and nanoparticles), and their applications in photocatalytic CO<sub>2</sub> reduction, hydrogen production, photooxidation and photocatalytic hydrogenation were summarized and discussed. Finally, the opportunities and challenges faced in this kind of MOFs-based composites were analyzed from different perspectives. This report is expected to help researchers design and develop high-performance MOFs-based photocatalytic materials.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 1","pages":"Article 110142"},"PeriodicalIF":9.4,"publicationDate":"2024-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142552831","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":"Light-controlled protein imprinted nanospheres with variable recognition specificity","authors":"Mingqi Wang, Shixin Fa, Jiate Yu, Guoxian Zhang, Yi Yan, Qing Liu, Qiuyu Zhang","doi":"10.1016/j.cclet.2024.110124","DOIUrl":"10.1016/j.cclet.2024.110124","url":null,"abstract":"<div><div>This work develops a protein imprinted nanosphere with varied recognition specificity for bovine serum albumin (BSA) and lysozyme (Lyz) under different UV light through a gradient dual crosslinked imprinting strategy (<em>i.e.</em>, covalent crosslinking and dynamic reversible crosslinking). The imprinting cavities are initially constructed using irreversible covalent crosslinking to specifically recognize BSA, and then the coumarin residues in the imprinting cavities are crosslinked under 365 nm UV light to further imprint Lyz, because Lyz has smaller size than BSA. Since the photo-crosslinking of coumarin is a reversible reaction, the imprinting cavities of Lyz can be de-crosslinked under 254 nm UV light and restore the imprinting cavities of BSA. Moreover, the <em>N</em>-isopropyl acrylamide (NIPAM) and pyrrolidine residues copolymerized in the polymeric surface of the nanospheres are temperature- and pH-responsive respectively. Therefore, the protein rebinding and release behaviors of the nanospheres are controlled by external temperature and pH. As a result, the materials can selectively separate BSA from real bovine whole blood and Lyz from egg white under different UV light. This study may provide a new strategy for construction of protein imprinted materials with tunable specificity for different proteins.</div></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"36 2","pages":"Article 110124"},"PeriodicalIF":9.4,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656944","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}
Sinong Wang , Shanshan Jin , Xue Yang , Yanyan Huang , Peng Liu , Yi Tang , Yuliang Yang
{"title":"Development of Mg-Al LDH and LDO as novel protective materials for deacidification of paper-based relics","authors":"Sinong Wang , Shanshan Jin , Xue Yang , Yanyan Huang , Peng Liu , Yi Tang , Yuliang Yang","doi":"10.1016/j.cclet.2024.109890","DOIUrl":"https://doi.org/10.1016/j.cclet.2024.109890","url":null,"abstract":"<div><p>Acidification of paper-based relics is a common problem, leading to their degradation and eventual loss. Paper deacidification is highly dependent on a limited variety of alkaline materials, and the development of new materials that are safe, efficient and easy-to-prepare is highly demanded to ensure a high level of safety and effective protection of paper-based relic. This study proposes the introduction of layered double hydroxide (LDH) and its calcined product, mixed metal oxide (layered double oxide (LDO)), as innovative protective materials for the deacidification of paper with varying levels of acidity. The results demonstrate that treatment with Mg-Al LDH/LDO can effectively modify the pH of acidic paper (<em>e.g.</em>, pH ∼ 4.0–6.4) to a neutral or weakly basic state, maintaining this desirable pH range even under long-term accelerated aging condition. Remarkably, LDH proves to be well-suited for the protection of slightly acidified paper (<em>e.g</em>., pH > 5.5), while LDO serves as an especially option for the deacidification of severely acidified paper (<em>e.g</em>., pH ≤ 5.5). During aqueous deacidification, due to the memory effect of the LDH-based materials, LDO is converted to rehydrated LDH, which creates a mild and appropriate alkaline retention in the paper, avoiding damage caused by strong alkalinity such as cellulose degradation and pigment fading during subsequent long-term natural preservation of the paper. Furthermore, Mg-Al LDH/LDO materials also exhibit flame-retardant and bacteriostatic properties. This opens up opportunities for the safe, efficient and multifunctional protection of acidified paper-based relics.</p></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"35 9","pages":"Article 109890"},"PeriodicalIF":9.1,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141424078","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":"2D photocatalysts for hydrogen peroxide synthesis","authors":"Liyong Ding , Zhenhua Pan , Qian Wang","doi":"10.1016/j.cclet.2024.110125","DOIUrl":"10.1016/j.cclet.2024.110125","url":null,"abstract":"<div><p>Photocatalytic hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>) synthesis, driven by solar energy, offers a sustainable and cleaner alternative for producing green H<sub>2</sub>O<sub>2</sub> from water and oxygen. 2D photocatalysts have emerged as powerful materials for this purpose due to their unique physiochemical properties such as a flexible planar structure and large surface area. This review provides a comprehensive overview of the latest advances in 2D photocatalytic materials employed in H<sub>2</sub>O<sub>2</sub> synthesis, including metal oxides, metal chalcogenides, bismuth-based materials, graphitic carbon nitrides (g-C<sub>3</sub>N<sub>4</sub>), metal−organic frameworks (MOFs), and covalent organic frameworks (COFs). Beginning with an extensive introduction to possible reaction routes for photocatalytic H<sub>2</sub>O<sub>2</sub> synthesis, we summarize the common methods for H<sub>2</sub>O<sub>2</sub> detection, crucial for obtaining reliable results in H<sub>2</sub>O<sub>2</sub> studies. Additionally, we highlight molecular-level modification strategies for 2D photocatalysts, such as surface modification, ion doping, defect engineering, and heterojunction construction, which promote high-efficiency solar-to-chemical conversion for sustainable H<sub>2</sub>O<sub>2</sub> photosynthesis. Furthermore, we discuss key issues and provide perspective outlooks for the efficient and sustainable generation of H<sub>2</sub>O<sub>2</sub> in scale-up industrial production. This review offers in-depth insights into different reaction pathways of H<sub>2</sub>O<sub>2</sub> synthesis and provides design principles for 2D photocatalysts to enhance H<sub>2</sub>O<sub>2</sub> production, guiding the development of efficient photocatalysts for H<sub>2</sub>O<sub>2</sub> synthesis.</p></div>","PeriodicalId":10088,"journal":{"name":"Chinese Chemical Letters","volume":"35 12","pages":"Article 110125"},"PeriodicalIF":9.4,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142149322","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}