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Advanced pH Indicators Consisting of BODIPY and Coumarin Fluorophores with a Guanidinyl Structure Capable of Methanol Recognition
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400605
Dr. Tomohiro Umeno , Mio Tanaka , Moeka Fujihara , Naoko Iizuka , Shota Matsumoto , Dr. Kazuteru Usui , Prof. Satoru Karasawa
{"title":"Advanced pH Indicators Consisting of BODIPY and Coumarin Fluorophores with a Guanidinyl Structure Capable of Methanol Recognition","authors":"Dr. Tomohiro Umeno ,&nbsp;Mio Tanaka ,&nbsp;Moeka Fujihara ,&nbsp;Naoko Iizuka ,&nbsp;Shota Matsumoto ,&nbsp;Dr. Kazuteru Usui ,&nbsp;Prof. Satoru Karasawa","doi":"10.1002/ajoc.202400605","DOIUrl":"10.1002/ajoc.202400605","url":null,"abstract":"<div><div>Guanidine is strongly basic and has a high molecular recognition ability. We previously developed a guanidine‐bearing benzoquinoline for the fluorescence detection of MeOH by exploiting the strong basicity of guanidine. The benzoquinoline fluorophore quantitatively detected MeOH in EtOH with moderate sensitivity and a limit of detection (LOD) of 16.5 %. In this study, we developed two guanidinyl boron dipyrromethene (BODIPY) and two guanidinyl coumarin fluorophores. These fluorophores have higher molar extinction coefficients (ϵ) than those of benzoquinolines, which suggests that they could have improved detection sensitivity. The BODIPY fluorophores exhibited acid‐responsive turn‐on fluorescence for MeOH, similar to the benzoquinoline fluorophore. Their high ϵ values led to an enhanced MeOH detection sensitivity of 1.3 % in EtOH. The coumarin derivatives exhibited acid‐responsive turn‐off fluorescence. In addition, the absorbance spectral shift of the protonated and neutral forms of coumarin enabled the ratiometric detection of MeOH (LOD=0.85 % and 0.57 %, respectively). This study demonstrates the utility of guanidine‐based fluorophores in molecular recognition and promotes the development of similar fluorophores in analytical chemistry.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400605"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424257","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
Alkylated Quinolines through Benzylic sp3 C−H Functionalization: Sequential Synthesis and Photophysical Studies
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400607
Sundararajan Suresh , Pari Keerthana , Prof. Dr. Fazlurrahman Nawaz Khan
{"title":"Alkylated Quinolines through Benzylic sp3 C−H Functionalization: Sequential Synthesis and Photophysical Studies","authors":"Sundararajan Suresh ,&nbsp;Pari Keerthana ,&nbsp;Prof. Dr. Fazlurrahman Nawaz Khan","doi":"10.1002/ajoc.202400607","DOIUrl":"10.1002/ajoc.202400607","url":null,"abstract":"<div><div>An efficient method has been developed for the green synthesis of alkylated quinolines <em>via</em> Cu‐TEMPO catalyzed dehydrogenation, and DEP/DES‐assisted benzylic C−H functionalization followed by cross Rauhut‐Currier type reaction. The reaction mechanism is elucidated through control experiments and <sup>1</sup>H NMR reaction monitoring. This transformation offers several advantages, including moderate to good yields of the desired products, mild reaction conditions, use of a cost‐effective metal catalyst, good functional group tolerance, and applicability to gram‐scale synthesis. Additionally, the synthetic utility and the photophysical properties of the synthesized alkylated quinoline derivatives were investigated.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400607"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423677","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
Diphenylperylene Isomers as Novel Emissive Organic Semiconductors
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400608
Liangliang Chen , Ying Wang , Zitong Liu
{"title":"Diphenylperylene Isomers as Novel Emissive Organic Semiconductors","authors":"Liangliang Chen ,&nbsp;Ying Wang ,&nbsp;Zitong Liu","doi":"10.1002/ajoc.202400608","DOIUrl":"10.1002/ajoc.202400608","url":null,"abstract":"<div><div>Emissive organic semiconductors are crucial for integrated optoelectronic devices, yet only a limited number of materials exhibit high mobility and high photoluminescence quantum yield because of the contradictory requirements for molecular stacking. In this study, two diphenylperylene isomers, <strong>39P‐Ph</strong> and <strong>310P‐Ph</strong>, were successfully synthesized through a one‐step process by varying the positions of the substituent phenyl groups on the perylene core. Both compounds were comprehensively characterized and demonstrated excellent hole transport capabilities and moderate photoluminescence quantum yield (PLQY), along with long‐wavelength emission, establishing them as effective emissive organic semiconductors. <strong>39P‐Ph</strong> emits orange‐yellow fluorescence in crystalline powder with an absolute PLQY of 15.4 % and <strong>310P‐Ph</strong> shows orange‐red emission with an emissive wavelength of up to 612 nm in 17.5 % PLQY. Moreover, the carrier mobilities of <strong>39P‐Ph</strong> and <strong>310P‐Ph</strong> are up to 3.05 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup> and 1.36 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively, based on the single‐crystal devices. These results reveal that <strong>39P‐Ph</strong> and <strong>310P‐Ph</strong> are promising candidates as emissive semiconductors, offering a balance between efficient charge transport and light emission for integrated optoelectronic applications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400608"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423678","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
Microcrystalline Cellulose and Cellulose Nanocrystals: Ecofriendly and Sustainable Support Materials in Heterogeneous Nanocatalysis for Green Organic Transformations
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400586
Vinay S. Sharma , Saloni Mishra , Anuj S. Sharma , Neha Sharma , Rajender S. Varma , Pranav S. Shrivastav , Achalkumar Ammathnadu Sudhakar
{"title":"Microcrystalline Cellulose and Cellulose Nanocrystals: Ecofriendly and Sustainable Support Materials in Heterogeneous Nanocatalysis for Green Organic Transformations","authors":"Vinay S. Sharma ,&nbsp;Saloni Mishra ,&nbsp;Anuj S. Sharma ,&nbsp;Neha Sharma ,&nbsp;Rajender S. Varma ,&nbsp;Pranav S. Shrivastav ,&nbsp;Achalkumar Ammathnadu Sudhakar","doi":"10.1002/ajoc.202400586","DOIUrl":"10.1002/ajoc.202400586","url":null,"abstract":"<div><div>The utilization of microcrystalline cellulose (MCC) and cellulose nanocrystals (CNC) as supports for nanocatalysts has garnered considerable interest in recent research due to their unique properties and several advantages. In this regard, we present a review of the use of MCC or CNC‐based nanocatalysts and their catalytic performance in organic reactions under milder and sustainable reaction conditions. The inherent advantages of MCC, such as its abundance, biocompatibility, and versatile surface, make it more attractive support material for nanocatalysts. Similarly, CNCs, with their high surface area, tunable surface chemistry, and sustainable nature, offer promising prospects for enhancing catalytic processes. The synergy between the cellulose‐based material and nanoparticles exhibits several novel properties. This review highlights the key features, advantages, and catalytic applications of MCC as well as CNC‐supported nanocatalysts, emphasizing their role in promoting more sustainable and efficient organic transformations.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400586"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423703","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
TEMPO‐Mediated Cross‐Dehydrogenative Coupling for the Synthesis of Bis(indolyl)methanes TEMPO 介导的交叉脱氢偶联合成双(吲哚基)甲烷
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400484
You‐Qiang Guo , Long Liang , Dr. Zhen‐Yu Wang , Prof. Xiang Wu , Prof. You‐Gui Li
{"title":"TEMPO‐Mediated Cross‐Dehydrogenative Coupling for the Synthesis of Bis(indolyl)methanes","authors":"You‐Qiang Guo ,&nbsp;Long Liang ,&nbsp;Dr. Zhen‐Yu Wang ,&nbsp;Prof. Xiang Wu ,&nbsp;Prof. You‐Gui Li","doi":"10.1002/ajoc.202400484","DOIUrl":"10.1002/ajoc.202400484","url":null,"abstract":"<div><div>A TEMPO‐mediated method has been developed for the synthesis of bis(indolyl)‐methane derivatives by the cross‐dehydrogenative coupling between C(sp<sup>3</sup>)−H of <em>para‐</em>cresol derivatives and C(sp<sup>2</sup>)−H of indoles in moderate yields under aqueous conditions. This method utilizes toluene derivatives as starting materials, allowing for coupling without the need for further functionalization. The use of environmentally friendly water as a solvent minimizes waste generation. Electron‐donating groups such as methyl and methoxy, as well as halogens like fluorine, chlorine, and bromine, exhibit good tolerance in this process. Furthermore, a possible reaction mechanism is proposed to elucidate the formation of BIMs.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400484"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665592","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
An Unconventional Redox‐Neutral Regioselective Iodoamination of Allenamides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400667
Zhe Tian , Zhaoxuan Zeng , Hongqiang Xie , Prof. Qing Liu , Dr. Fachao Yan , Prof. Hui Liu
{"title":"An Unconventional Redox‐Neutral Regioselective Iodoamination of Allenamides","authors":"Zhe Tian ,&nbsp;Zhaoxuan Zeng ,&nbsp;Hongqiang Xie ,&nbsp;Prof. Qing Liu ,&nbsp;Dr. Fachao Yan ,&nbsp;Prof. Hui Liu","doi":"10.1002/ajoc.202400667","DOIUrl":"10.1002/ajoc.202400667","url":null,"abstract":"<div><div>A novel unconventional redox‐neutral regioselective iodoamination of allenamides was developed. In the absence of metal catalyst, base and oxidant, the selective iodoamination of allenamides was achieved by using iodide salt in combination with morpholine/imidazole. The Iodide‐substituted <em>Z</em>‐enamides were synthesized under mild reaction conditions, and the products were stable and highly amenable to further modification.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400667"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423907","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 γ‐Alkenylated δ‐Sultones Via Brønsted Base‐Catalyzed Annulative SuFEx Reaction of Allyl Ketones and Ethenesulfonyl Fluorides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400619
Qichao Zhang , Fang Zhang , Zhihang Wei , Xiangyi Shi , Lin He , Jichang Liu , Guangfen Du
{"title":"Synthesis of γ‐Alkenylated δ‐Sultones Via Brønsted Base‐Catalyzed Annulative SuFEx Reaction of Allyl Ketones and Ethenesulfonyl Fluorides","authors":"Qichao Zhang ,&nbsp;Fang Zhang ,&nbsp;Zhihang Wei ,&nbsp;Xiangyi Shi ,&nbsp;Lin He ,&nbsp;Jichang Liu ,&nbsp;Guangfen Du","doi":"10.1002/ajoc.202400619","DOIUrl":"10.1002/ajoc.202400619","url":null,"abstract":"<div><div>A tandem annulation reaction of allyl ketones and β‐aryl ethenesulfonyl fluorides has been described. Under the catalysis of Brønsted base, allyl ketones reacted with β‐aryl ethenesulfonyl fluorides through a tandem intermolecular Michael addition‐intramolecular SuFEx process to afford γ‐alkenylated δ‐sultones in good to excellent yields. In this reaction, no additional base was needed, and 4 Å molecular sieves were used as efficient HF scavenger to restrict the neutralization and deactivation of the Brønsted base catalyst.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400619"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424309","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
Sc(OTf)3‐Catalyzed Tunable Thio‐(3+3) Annulation Reactions of Indoline‐2‐thiones with α‐Benzylidene‐β‐tetralones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400452
Yan Jiang , Hao‐Jie Ma , Chen‐Ying Zhai , Xue‐Long Wang , Yi Yang
{"title":"Sc(OTf)3‐Catalyzed Tunable Thio‐(3+3) Annulation Reactions of Indoline‐2‐thiones with α‐Benzylidene‐β‐tetralones","authors":"Yan Jiang ,&nbsp;Hao‐Jie Ma ,&nbsp;Chen‐Ying Zhai ,&nbsp;Xue‐Long Wang ,&nbsp;Yi Yang","doi":"10.1002/ajoc.202400452","DOIUrl":"10.1002/ajoc.202400452","url":null,"abstract":"<div><div>A Sc(OTf)<sub>3</sub>‐catalyzed tunable thio‐Michael addition/nucleophilic addition/dehydration reaction of indoline‐2‐thiones with α‐benzylidene‐β‐tetralones was realized, leading to biologically important tetrahydrobenzo[7,8]isothiochromeno[3,4‐b]indoles and thiazino[3,2‐a]indoles in moderate to good yields. Moreover, by extending the reaction time, the dehydrogenated cycloadducts dihydrobenzo[7,8]isothiochromeno[3,4‐b]indoles were also obtained from the reaction of indoline‐2‐thiones with α‐benzylidene‐β‐tetralones.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400452"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424029","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
A Comprehensive Review on Construction of Biologically Active α‐Carbolines From Synthetic And Natural Origin.
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400570
Ankur Gupta , Pratiksha Khanal , Joydev K. Laha
{"title":"A Comprehensive Review on Construction of Biologically Active α‐Carbolines From Synthetic And Natural Origin.","authors":"Ankur Gupta ,&nbsp;Pratiksha Khanal ,&nbsp;Joydev K. Laha","doi":"10.1002/ajoc.202400570","DOIUrl":"10.1002/ajoc.202400570","url":null,"abstract":"<div><div>α‐Carboline is an important scaffold present in various synthetic and naturally obtained bioactive compounds possessing a wide range of pharmacological properties. Hence, in the current comprehensive review, we intend to present the main routes to the synthesis of α‐carboline analogs based on various pathways such as pyrrole, benzene, and pyridine ring annulation. The pathways include either or combinations of transition metal‐catalyzed amination/arylation, Graebe‐Ullmann reaction (thermal pyrolysis, photochemical cyclization), Diels‐Alder cycloaddition and condensation reactions, <em>N</em>‐Heterocyclic carbene catalysed reactions, decarboxylative annulation, etc. of substituted benzene, pyridine, quinoline, and indole derivatives in order to compare the potential of synthetic routes of this series and consolidate the development, current status and perspectives for the design of α‐carboline analogs. Various pharmacological and spectroscopy functions of the compounds belonging to this class are summarized herewith. It also discusses the synthesis of functionalized bioactive naturally obtained hetero‐annulated α‐carbolines.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400570"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423701","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
A Sustainable Catalyst‐Free Approach to Bipyrazoles Under Batch and Flow Chemistry Techniques
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400583
Akanksha Kumari , Anshul Jain , Dr. Nirmal K. Rana
{"title":"A Sustainable Catalyst‐Free Approach to Bipyrazoles Under Batch and Flow Chemistry Techniques","authors":"Akanksha Kumari ,&nbsp;Anshul Jain ,&nbsp;Dr. Nirmal K. Rana","doi":"10.1002/ajoc.202400583","DOIUrl":"10.1002/ajoc.202400583","url":null,"abstract":"<div><div>We have developed an efficient and sustainable approach for the synthesis of 4,4′‐bipyrazole derivatives from spirocyclopropanyl‐pyrazolone and hydrazine under mild conditions. This methodology is catalyst‐free, operating effectively in both batch and continuous flow processes. The flow synthesis allows the production of products up to 110 mg/h which provides industrial applicability and scalability. Additionally, 4,4’‐bipyraole has been transformed into a triphenyl‐substituted pyrazole derivative.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400583"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424273","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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