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Theoretical analysis on the formation and nitric oxide release of N-heterocyclic carbene nitric oxide radicals 关于 N-杂环碳一氧化氮自由基的形成和一氧化氮释放的理论分析
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-03-18 DOI: 10.1002/bkcs.12837
Junbeom Park, Hayoung Song, Yong Ho Lee, Eunsung Lee
{"title":"Theoretical analysis on the formation and nitric oxide release of N-heterocyclic carbene nitric oxide radicals","authors":"Junbeom Park,&nbsp;Hayoung Song,&nbsp;Yong Ho Lee,&nbsp;Eunsung Lee","doi":"10.1002/bkcs.12837","DOIUrl":"10.1002/bkcs.12837","url":null,"abstract":"<p>The theoretical study on the fixation and release of nitric oxide (NO) by <i>N</i>-heterocyclic carbenes (NHCs) is explored by utilizing a multivariate linear regression approach. We utilized data-driven tools to establish correlations between molecular descriptors of NHC and reaction outputs of the formation and NO release of NHC nitric oxide radicals (NHCNOs). A key electronic parameter, the singlet-triplet energy gap (ΔE<sub>ST</sub>), plays a pivotal role in the thermodynamics of NHCNO formation (ΔG<sub>f</sub>) and NO release (ΔG<sub>r</sub>). The activation energy models highlight HOMO energy level (E<sub>HOMO</sub>), C–N bond length (<i>d</i><sub>C–N</sub>), and NBO charge on N atom (<i>q</i><sup>NBO</sup><sub>N</sub>) as crucial factors for the formation of NHCNO (ΔG<sup>‡</sup><sub>f</sub>), while the activation energy for the NO release (ΔG<sup>‡</sup><sub>r</sub>) significantly correlates with free energy difference (ΔG<sub>r</sub>), resulting a strong ΔE<sub>ST</sub> dependency. This study provides valuable insights into the thermodynamics and kinetics of NHCNO processes, offering predictive capabilities to design NHCs tailored for NO release.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 5","pages":"404-411"},"PeriodicalIF":1.7,"publicationDate":"2024-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140147976","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Solid-phase synthetic method for N-alkyl-7-alkylamino-2-aryloxazolo[5,4-d]pyrimidine-5-carboxamide derivatives N-烷基-7-烷基氨基-2-芳基恶唑并[5,4-d]嘧啶-5-甲酰胺衍生物的固相合成方法
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-03-11 DOI: 10.1002/bkcs.12834
Min Ju Cho, Hye Won Yang, Moon-Kook Jeon
{"title":"Solid-phase synthetic method for N-alkyl-7-alkylamino-2-aryloxazolo[5,4-d]pyrimidine-5-carboxamide derivatives","authors":"Min Ju Cho,&nbsp;Hye Won Yang,&nbsp;Moon-Kook Jeon","doi":"10.1002/bkcs.12834","DOIUrl":"10.1002/bkcs.12834","url":null,"abstract":"<p>Oxazolo[5,4-<i>d</i>]pyrimidine derivatives have been reported to exhibit interesting biological activities. Herein, we described a solid-phase synthetic method to produce <i>N</i>-alkyl-7-alkylamino-2-aryloxazolo[5,4-<i>d</i>]pyrimidine-5-carboxamide derivatives. The strategy consists of loading the template compounds (i.e., 2-aryl-6,7-dihydrooxazolo[5,4-<i>d</i>]pyrimidin-7-one-5-carboxylic acids) onto aminated acid-sensitive methoxybenzaldehyde (AMEBA) resins, the subsequent benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP)-mediated direct amination with primary/secondary amines, and the final cleavage from the solid support to afford the target compounds. The template 2-aryl-6,7-dihydrooxazolo[5,4-<i>d</i>]pyrimidin-7-one-5-carboxylic acids were prepared using a five-step solution-phase synthetic route from ethyl 2-cyano-2-(hydroxyimino)acetate. BOP-mediated direct amination conditions were optimized by a solution-phase model study. The solid-phase synthetic method provided the 17 target compounds in 16%–92% five-step overall isolated yields from the Merrified resin for selected template compounds and primary/secondary amines.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 5","pages":"460-471"},"PeriodicalIF":1.7,"publicationDate":"2024-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/bkcs.12834","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140115094","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Trifluoroacetyl-effect on amino-single benzene-based fluorophores: Synthesis, optical properties, and cytotoxicity 氨基单苯基荧光团的三氟乙酰效应：合成、光学特性和细胞毒性
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-03-10 DOI: 10.1002/bkcs.12836
Ji Hye Jin, Dopil Kim, Jisoo Kang, Sangho Lee, Jong Min An, Min Kim, Dokyoung Kim
{"title":"Trifluoroacetyl-effect on amino-single benzene-based fluorophores: Synthesis, optical properties, and cytotoxicity","authors":"Ji Hye Jin,&nbsp;Dopil Kim,&nbsp;Jisoo Kang,&nbsp;Sangho Lee,&nbsp;Jong Min An,&nbsp;Min Kim,&nbsp;Dokyoung Kim","doi":"10.1002/bkcs.12836","DOIUrl":"10.1002/bkcs.12836","url":null,"abstract":"<p>Amino-single benzene-based fluorophores (SBBFs) are representative small-size fluorescent dyes that have an electron push-pull structure within the benzene core. In this work, a new library of amino-SBBFs, which have trifluoroacetyl moiety at the electron-pushing amine group (named SBBF-TFA), featuring a variety of methylamines, dimethylamines, as well as acetyl. To explore the SBBF-TFA library, we conducted (i) library synthesis, (ii) assessment of various photophysical properties in nine different types of organic/aqueous solvents, and (iii) evaluation of cytotoxicity in the HeLa cell line. We believe that our findings provide valuable insights for advancing novel small-molecule fluorescent probes and materials with diverse applications across pharmacochemical fields.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 5","pages":"451-455"},"PeriodicalIF":1.7,"publicationDate":"2024-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140099089","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent interlayer and separator design approaches for high-performance Li–S batteries 用于高性能锂-S 电池的最新层间和隔膜设计方法
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-03-07 DOI: 10.1002/bkcs.12833
Hyo-Yeol Choi, Si-Hwan Lee, Hyuk-Joon Yu, Seung-Ho Yu
{"title":"Recent interlayer and separator design approaches for high-performance Li–S batteries","authors":"Hyo-Yeol Choi,&nbsp;Si-Hwan Lee,&nbsp;Hyuk-Joon Yu,&nbsp;Seung-Ho Yu","doi":"10.1002/bkcs.12833","DOIUrl":"10.1002/bkcs.12833","url":null,"abstract":"<p>Lithium–sulfur batteries (LSBs) have attracted attention as promising next-generation batteries due to their remarkably high capacity compared to lithium-ion batteries and the low cost of sulfur. However, one of the inherent problems of LSBs is the “shuttle effect,” which causes lithium metal anode instability and capacity fading. This is still a major barrier that must be overcome before it is used in the industry. Therefore, to commercialize LSBs, it is essential to suppress this shuttle effect. From this point of view, this review focuses on the categorization of the methods and materials for interlayer and separator modification, which is one of the effective ways to address the shuttle effect.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 5","pages":"382-397"},"PeriodicalIF":1.7,"publicationDate":"2024-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140258555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Development of a machine-learning model for microplastic analysis in an FT-IR microscopy image 开发用于傅立叶变换红外显微镜图像中微塑料分析的机器学习模型
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-03-07 DOI: 10.1002/bkcs.12835
Eunwoo Choi, Yejin Choi, Hyoyoung Lee, Jae-Woo Kim, Han Bin Oh
{"title":"Development of a machine-learning model for microplastic analysis in an FT-IR microscopy image","authors":"Eunwoo Choi,&nbsp;Yejin Choi,&nbsp;Hyoyoung Lee,&nbsp;Jae-Woo Kim,&nbsp;Han Bin Oh","doi":"10.1002/bkcs.12835","DOIUrl":"10.1002/bkcs.12835","url":null,"abstract":"<p>The escalating concern regarding microplastics (MPs) in the environment has recently accentuated the need for comprehensive analyses across various matrices. Fourier Transfrom Infrared (FT-IR) microscopy is widely used method for MP identification, but challenges arise due to the presence of secondary materials on real samples, causing inaccuracies in spectral matching. To tackle this issue, we propose a solution: a 1D-convolution neural network (1D-CNN) machine-learning model classifying FT-IR spectra into 16 polymer species. Using a dataset of 5413 spectra, with 80% (4330) for training and 20% (1083) for external testing, our method achieved 98.59% accuracy for cross-validation and 92.34% for external validation. This study underscores the efficacy of machine learning in discerning polymer types among MPs, even in real samples tainted by secondary materials. The implementation of our 1D-CNN model marks a significant leap in overcoming conventional method limitations, providing a robust tool for accurately unraveling MPs intricacies in environmental matrices.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 5","pages":"472-481"},"PeriodicalIF":1.7,"publicationDate":"2024-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140073493","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Au nanoparticle-catalyzed electron transfer from ammonia-borane to Ru(NH3)63+ for sensitive biosensing 金纳米粒子催化电子从氨硼烷转移到 Ru(NH3)63+ 以实现灵敏的生物传感
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-03-05 DOI: 10.1002/bkcs.12831
Seonhwa Park, Aman Bhatia, Ponnusamy Nandhakumar, Jihyeon Kim, Haesik Yang
{"title":"Au nanoparticle-catalyzed electron transfer from ammonia-borane to Ru(NH3)63+ for sensitive biosensing","authors":"Seonhwa Park,&nbsp;Aman Bhatia,&nbsp;Ponnusamy Nandhakumar,&nbsp;Jihyeon Kim,&nbsp;Haesik Yang","doi":"10.1002/bkcs.12831","DOIUrl":"https://doi.org/10.1002/bkcs.12831","url":null,"abstract":"<p>Metal nanoparticle (NP)-catalyzed electron transfer (ET) from a reducing agent to a metal complex is useful for signal amplification in biosensors. For efficient ET, the metal complex must undergo rapid outer-sphere reactions, be highly water-soluble, and effectively penetrate bio/organic layers on metal NPs. Our study identifies Ru(NH<sub>3</sub>)<sub>6</sub><sup>3+</sup> as well-suited for this purpose. Among reducing agents, ammonia-borane (AB) enables rapid metal NP-catalyzed ET, with Au, Pt, and Pd NPs displaying similar catalytic activities. The pseudo second-order rate constant for 20-nm Au NP-catalyzed ET from AB to Ru(NH<sub>3</sub>)<sub>6</sub><sup>3+</sup> (1.4 × 10<sup>8</sup> M<sup>−1</sup> s<sup>−1</sup>) approaches the diffusion-controlled rate constant. Despite immunoglobulin G and bovine serum albumin passively adsorbed on Au NPs, catalytic activity remains largely unaffected. Applying Au NP-catalyzed ET to prostate-specific antigen detection in human serum achieves a low detection limit of 10 pg/mL. These findings highlight the potential of Ru(NH<sub>3</sub>)<sub>6</sub><sup>3+</sup> and AB in designing biosensors based on rapid catalytic reaction.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 4","pages":"366-372"},"PeriodicalIF":1.7,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140556160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total synthesis of cypripedin 氰戊菊酯的全合成
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-02-28 DOI: 10.1002/bkcs.12832
Hyun Jung Kim, Bok Yun Kang, Jung-Hyun Shim, Seung-Sik Cho, Eunae Kim, Goo Yoon
{"title":"Total synthesis of cypripedin","authors":"Hyun Jung Kim,&nbsp;Bok Yun Kang,&nbsp;Jung-Hyun Shim,&nbsp;Seung-Sik Cho,&nbsp;Eunae Kim,&nbsp;Goo Yoon","doi":"10.1002/bkcs.12832","DOIUrl":"10.1002/bkcs.12832","url":null,"abstract":"<p>The first facile synthesis of cypripedin (<b>1</b>) was achieved using commercially available 2,3-dihydroxybenzaldehyde (<b>2</b>) and 5-bromovanillin (<b>4</b>) via a convergent strategy involving the Mizoroki–Heck reaction and photocyclization as key steps.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 4","pages":"359-361"},"PeriodicalIF":1.7,"publicationDate":"2024-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139988114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cover Picture: Molecular Structural Descriptor-Assisted Machine Learning for Organic Photovoltaics with Perylenediimide Acceptors (BKCS 1/2024) Gyu-Hee Kim, Keonho Yoon, Chihyung Lee, Minwoo Nam, Doo-Hyun Ko 封面图片：使用过二亚胺受体的有机光伏分子结构描述符辅助机器学习 (BKCS 1/2024) Gyu-Hee Kim、Keonho Yoon、Chihyung Lee、Minwoo Nam、Doo-Hyun Ko
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-02-23 DOI: 10.1002/bkcs.12726
{"title":"Cover Picture: Molecular Structural Descriptor-Assisted Machine Learning for Organic Photovoltaics with Perylenediimide Acceptors (BKCS 1/2024) Gyu-Hee Kim, Keonho Yoon, Chihyung Lee, Minwoo Nam, Doo-Hyun Ko","authors":"","doi":"10.1002/bkcs.12726","DOIUrl":"https://doi.org/10.1002/bkcs.12726","url":null,"abstract":"<p>The cover picture illustrates the artificial intelligence model that predicts the performance of organic photovoltaics. This model predicts how organic photovoltaics will perform under 1 sun AM 1.5 G illumination by using only the molecular structure of the organic semiconductors within the bulk heterojunction photoactive layer. The organic semiconductors of the target organic photovoltaics comprise polymer donors and bay-position-linked diperylenediimide acceptors. More details are available in the article Gyu-Hee Kim, Keonho Yoon, Chihyung Lee, Minwoo Nam, Doo-Hyun Ko<figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 2","pages":"89"},"PeriodicalIF":1.7,"publicationDate":"2024-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/bkcs.12726","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139937243","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Rise of atomically dispersed metal catalysts: Are they a new class of catalysts? 原子分散金属催化剂的兴起：它们是一类新型催化剂吗？
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-02-22 DOI: 10.1002/bkcs.12830
Jae Hyung Kim, Sang Hoon Joo
{"title":"Rise of atomically dispersed metal catalysts: Are they a new class of catalysts?","authors":"Jae Hyung Kim,&nbsp;Sang Hoon Joo","doi":"10.1002/bkcs.12830","DOIUrl":"10.1002/bkcs.12830","url":null,"abstract":"<p>Atomically dispersed metal catalysts or single-atom catalysts have made great strides during the past decade in the catalysis field. While an initial vision of atomically dispersed metal catalysts was to combine the advantages of homogeneous and heterogeneous catalysts, their unexpected potentials continue to be discovered. In this account, we introduce historical backgrounds underpinning the emergence of atomically dispersed metal catalysts. Next, we illustrate some recent examples demonstrating the unusual reactivities of atomically dispersed metal catalysts, which are hard to realize by homogeneous or heterogeneous catalysts. We conclude the account by suggesting the remaining challenges in this exciting field.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 4","pages":"350-358"},"PeriodicalIF":1.7,"publicationDate":"2024-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139953536","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of C21-C41 fragment of the reported structure of Neaumycin B 合成新霉素 B 已报告结构的 C21-C41 片段
IF 1.7 4区 化学
Bulletin of the Korean Chemical Society Pub Date : 2024-02-22 DOI: 10.1002/bkcs.12825
Eun Gyeong Choi, Eun Bi Kim, Duck Hyung Lee
{"title":"Synthesis of C21-C41 fragment of the reported structure of Neaumycin B","authors":"Eun Gyeong Choi,&nbsp;Eun Bi Kim,&nbsp;Duck Hyung Lee","doi":"10.1002/bkcs.12825","DOIUrl":"10.1002/bkcs.12825","url":null,"abstract":"<p>Stereoselective synthesis of the C<sub>21</sub>-C<sub>41</sub> fragment <b>4</b> of the reported structure of Neaumycin B(<b>1</b>), a 28-membered macrolide compound with 19-chiral centers and 6,6-spiroketal structure, has been described. C<sub>21</sub>-C<sub>27</sub> fragment <b>5</b> was synthesized from the commercially available <i>(S)</i>-Roche ester <b>7</b> using stereoselective allylation and Brown <i>anti</i>-crotylation as key steps. C<sub>28</sub>-C<sub>41</sub> fragment <b>6</b> was constructed from chiral oxazolidinone auxiliary <b>13</b> using Evans <i>syn</i>-aldol reaction, diastereoselective epoxidation, and <i>(S)</i>-CBS reduction as key steps. Finally, boron-mediated acetate aldol reaction of <b>5</b> and <b>6</b> led to the synthesis of C<sub>21</sub>-C<sub>41</sub> fragment <b>4</b> for the reported structure of Neaumycin B (<b>1</b>).</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":"45 4","pages":"362-365"},"PeriodicalIF":1.7,"publicationDate":"2024-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139953135","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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