European Journal of Organic Chemistry最新文献

Photochemical Synthesis of 2,6‐Linked Anthracene Oligomers without Introducing Extra Substituents 不引入额外取代基的2,6 -链蒽低聚物光化学合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-29 DOI: 10.1002/ejoc.202500490

Hironobu Hayashi, Noburu Tsunoda, Shoma Kasahara, Chie Negoro, Yee Seng Chan, Naoki Aratani, Hiroko Yamada

{"title":"Photochemical Synthesis of 2,6‐Linked Anthracene Oligomers without Introducing Extra Substituents","authors":"Hironobu Hayashi, Noburu Tsunoda, Shoma Kasahara, Chie Negoro, Yee Seng Chan, Naoki Aratani, Hiroko Yamada","doi":"10.1002/ejoc.202500490","DOIUrl":"https://doi.org/10.1002/ejoc.202500490","url":null,"abstract":"Photoconvertible precursors of 2,6‐linked anthracene oligomers (trimer, tetramer, and pentamer) were synthesized through repeated Suzuki‐Miyaura cross‐coupling reactions. Upon exposure of these precursors to light at 450 nm, which correspond to the n–π* transition of diketone moieties, yellow precipitates were formed, suggesting the conversion to the corresponding anthracene oligomers from the precursors. The disappearance of 1H NMR peaks after photoirradiation indicated the formation of anthracene oligomers with less solubility. High‐resolution mass spectrometry evidently indicated the oligomer formations, and infrared spectral analysis for thin films showed the disappearance of peaks originating from the carbonyl groups, also supporting the conversion. The absorption spectra after photoirradiation indicated a red‐shift in the absorption peaks accompanying oligomer formations, suggesting an extension of the π‐conjugated system. The low solubility of the resulting anthracene oligomers in organic solvents highlights the effectiveness of this synthetic strategy using the photoconvertible precursor. This study provides a practical method to synthesize acene oligomers without the introduction of extra substituents.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144165009","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Cover Feature: Amphiphilic Fluoro-Functionalized Cellulosic Materials: Synthesis, Characterization, and Organic Dye Adsorption Properties (Eur. J. Org. Chem. 20/2025) 封面特征：两亲性氟功能化纤维素材料：合成，表征和有机染料吸附性能(Eur。j . Org。化学20/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-28 DOI: 10.1002/ejoc.202582002

Davide Ricci, Andrea Maio, Christian Jahns, Elena Piacenza, Delia Francesca Chillura Martino, Roberto Scaffaro, Margit Schulze, Andrea Pace, Carla Rizzo, Ivana Pibiri

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9,9-Bis(4-diphenylaminophenyl)fluorene Modified Naphthothiadiazoles as Ambipolar Non-doped Near-Infrared Emitters for High-Efficiency Electroluminescent Devices 9,9-双（4-二苯基氨基苯基）芴修饰的双极性非掺杂近红外高效电致发光器件

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-28 DOI: 10.1002/ejoc.202500413

Vinich Promarak, Phatsathorn Chonlateeroj, Rattanasiri Wannapakdee, Wijitra Waengdongbung, Phakjira Chaimongkol, Trirath Sukthawee, Taweesak Sudyoadsuk, Pisist Kumnorkaew

{"title":"9,9-Bis(4-diphenylaminophenyl)fluorene Modified Naphthothiadiazoles as Ambipolar Non-doped Near-Infrared Emitters for High-Efficiency Electroluminescent Devices","authors":"Vinich Promarak, Phatsathorn Chonlateeroj, Rattanasiri Wannapakdee, Wijitra Waengdongbung, Phakjira Chaimongkol, Trirath Sukthawee, Taweesak Sudyoadsuk, Pisist Kumnorkaew","doi":"10.1002/ejoc.202500413","DOIUrl":"https://doi.org/10.1002/ejoc.202500413","url":null,"abstract":"Herein, we report the synthesis and characterization of efficient ambipolar charge-carrier transporting deep-red to near-infrared (NIR) fluorophores, namely MNTFT, PNTFT, and BMNTFT, based on an asymmetric donor-acceptor-donor' (D-A-D') structure, as well as their application as non-doped emitters in NIR organic light-emitting diodes (OLEDs). The molecules comprise naphtho[2,3-c][1,2,5]thiadiazole (Nz) as a strong A, bis(4-diphenylaminophenyl)fluorene as D, and either diphenylamine or dimethylaminophenyl as D'. Both experimental and theoretical investigations confirm that they exhibit hybridized local and charge-transfer (HLCT) excited states, which enable the pathways for harvesting triplet hot exciton via high-lying reverse intersystem crossing (hRISC) with intense NIR emissions (∼708 nm). Their asymmetrical D-A-D' features benefit well-balanced hole and electron mobilities, resulting in a successful application as a non-doped emissive layer in the OLEDs with decent performance. Particularly, the MNTFT-based non-doped device shows an NIR emission with a peak at 710 nm, a high maximum external quantum efficiency (EQEmax) of 2.51%, and a low turn-on voltage of 3.2 V. These results represent a significant advancement in the development of NIR fluorescent materials and OLED devices, meeting key requirements for various applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154291","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Metal‐Free HFIP‐Promoted Synthesis of Benzhydryl Derivatives from Stilbenes as Masked Electrophiles under Oxidative Conditions 在氧化条件下，无金属HFIP促进二苯乙烯作为掩蔽亲电试剂合成苯甲酸衍生物

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-28 DOI: 10.1002/ejoc.202500547

Francisco J. Sierra-Molero, Alejandro Baeza, Diego A. Alonso, Hernan Rico-Trilles

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Front Cover: Recent Developments for the Ring Opening of Pyrrolidines and Unstrained Cyclic Amines via C−N Bond Cleavage (Eur. J. Org. Chem. 20/2025) 封面：通过C - N键裂解吡咯烷和非张力环胺开环的最新进展。j . Org。化学20/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-28 DOI: 10.1002/ejoc.202582001

Eisuke Ota, Junichiro Yamaguchi

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Nitrile N‐Oxide‐based Fluorescent Probe to Impart Aggregation‐Induced Emission to Alkenes 腈- N -氧化物基荧光探针对烯烃的聚集诱导发射

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-28 DOI: 10.1002/ejoc.202500526

Yuki Oku, Ayaka Ito, Noriyuki Nakajima, Masahiro Hamada, Yasuhito Koyama

{"title":"Nitrile N‐Oxide‐based Fluorescent Probe to Impart Aggregation‐Induced Emission to Alkenes","authors":"Yuki Oku, Ayaka Ito, Noriyuki Nakajima, Masahiro Hamada, Yasuhito Koyama","doi":"10.1002/ejoc.202500526","DOIUrl":"https://doi.org/10.1002/ejoc.202500526","url":null,"abstract":"Fluorescent probes have been used extensively in chemical biology, allowing the visual observation of bioactive compounds. While many variations of fluorescent probes that react to polar functional groups have been developed, there are few fluorescent probes that directly modify less polar compounds. In this paper, pyrene‐containing nitrile N‐oxide (Pyrene‐NO) has been designed and synthesized as a fluorescent dye clickable to alkenes without a catalyst. Pyrene‐NO shows good reactivity to a terminal alkene, a polymer methacrylate, and a natural unsaturated lipid with internal alkenes to give the corresponding cycloadducts with pyrene as the fluorescent dye. The cycloadducts show aggregation‐induced emission (AIE) behaviors in a poor solvent. While the adducts to 1‐hexene or polymer methacrylate show AIE in water, the adduct to castor oil as a natural glycerolipid shows AIE in MeOH. The AIE behaviors are evidenced by the dependence of fluorescence intensity on the concentration and the enhanced fluorescence at 77 K compared with that at room temperature. It is suggested that aggregation of the cycloadduct in the poor solvent would kinetically suppress the non‐radiative deactivation of the excited state of pyrene based on interactions with oxygen, leading to an increase in fluorescence intensity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"134 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144165010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Front Cover: O-C Glycoside Rearrangement through Time-Controlled Electrochemical Flow Strategy: Switching between Kinetics and Thermodynamics (Eur. J. Org. Chem. 19/2025) 前封面：通过时间控制电化学流动策略的O-C糖苷重排：在动力学和热力学之间切换。j . Org。化学19/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-27 DOI: 10.1002/ejoc.202581901

Dr. Yosuke Ashikari, Yiyue Yao, Takuma Kudo, Dr. Masahiro Takumi, Prof. Dr. Aiichiro Nagaki

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Synthesis of β-N-Heterocyclic-Cyclobutane-Fused Bicyclic γ-Lactones from 2-Hydroxycyclobutanone and Carboxamide-Bearing Wittig Reagents 由2-羟基环丁酮和含羧胺的Wittig试剂合成β- n -杂环-环丁烷-融合双环γ-内酯

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-26 DOI: 10.1002/ejoc.202500332

Stefano Barranco, Mauro Uras, Veronica Frau, Pierluigi Caboni, Régis Guillot, David J. Aitken, Angelo Frongia

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Front Cover: Recent Advances in Chalcogenation of α-Amino Acids/Peptides: Synthetic and Mechanistic Aspects (Eur. J. Org. Chem. 18/2025) 封面：α-氨基酸/多肽硫代化的最新进展：合成和机制方面。j . Org。化学18/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-24 DOI: 10.1002/ejoc.202581801

Raghunath Bag, Malobika Kar, Nagendra K. Sharma

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Front Cover: Multigram Synthesis of 3-Azabicyclo[3.1.1]heptane Derivatives Including Bicyclic Thalidomide Analogs (Eur. J. Org. Chem. 17/2025) 封面：包括双环沙利度胺类似物在内的3-氮杂双环[3.1.1]庚烷衍生物的多元合成。j . Org。化学17/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-05-22 DOI: 10.1002/ejoc.202581701

Viacheslav Lysenko, Anton Portiankin, Oleh Shyshlyk, Timur Savchenko, Kostiantyn Nazarenko, Alexander Kostyuk, Oleksandr V. Golovchenko, Volodymyr S. Brovarets, Oleksandr O. Grygorenko

{"title":"Front Cover: Multigram Synthesis of 3-Azabicyclo[3.1.1]heptane Derivatives Including Bicyclic Thalidomide Analogs (Eur. J. Org. Chem. 17/2025)","authors":"Viacheslav Lysenko, Anton Portiankin, Oleh Shyshlyk, Timur Savchenko, Kostiantyn Nazarenko, Alexander Kostyuk, Oleksandr V. Golovchenko, Volodymyr S. Brovarets, Oleksandr O. Grygorenko","doi":"10.1002/ejoc.202581701","DOIUrl":"https://doi.org/10.1002/ejoc.202581701","url":null,"abstract":"<p><b>The Front Cover</b> shows a wizard casting a conformational restriction spell onto a molecule of thalidomide. The magical transformation leads to a 3-azabicyclo[3.1.1]heptane derivative—a promising scaffold for potential drug-discovery applications. In their Research Article (DOI: 10.1002/ejoc.202400938), O. O. Grygorenko and co-authors describe a multigram synthetic approach toward such molecules (with almost no magic involved). In particular, a series of 1-substituted 3-azabicyclo[3.1.1]heptanes, that is, monoprotected diamine building blocks, thalidomide analogs, and troxipide mimetics, were prepared with high efficiency. Artwork by Vitalii Boklashchuk.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144108950","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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