Chemistry - An Asian Journal最新文献

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Synthesis of 5-Selenosubstituted Spirocyclopenta[b]pyridine-2,5-dien-4-ones and Benzo[h]quinolines via Radical Cyclization of Arylethynylpyridines 通过芳炔基吡啶的自由基环化合成 5-硒代螺环戊并[b]吡啶-2,5-二烯-4-酮和苯并[h]喹啉类化合物

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-19 DOI: 10.1002/asia.202400974

Ricardo H. Bartz, Rafaela R. S. A. Santos, Paola S. Hellwig, Márcio S. Silva, Eder Joao Lenardao, Raquel G. Jacob, Gelson Perin

A practical strategy for obtaining novel 5-seleno-substituted spirocyclopenta[b]pyridines-2,5-dien-4-ones and benzo[h]quinolines via radical cyclization is reported. The synthetic protocol explores the reaction between arylethynylpyridines and diorganyl diselenides in acetonitrile as solvent and Oxone® as oxidant at 82 °C. This easy-to-handle, eco-friendly metal-free approach was carried out under an open atmosphere, affording functionalized organoselenium compounds in good to excellent yields. Control experiments and scale-up test were performed to demonstrate the efficiency of this methodology.

报告了一种通过自由基环化获得新型 5-硒代螺环戊并[b]吡啶-2,5-二烯-4-酮和苯并[h]喹啉的实用策略。合成方案探讨了芳基乙炔基吡啶和二芳基二硒化物在乙腈（溶剂）和 Oxone® （氧化剂）中于 82 ℃ 发生的反应。这种易于处理、环保的无金属方法是在开放气氛下进行的，可获得良好至极佳产率的官能化有机硒化合物。为证明该方法的有效性，还进行了对照实验和放大试验。

引用次数: 0

Creation of Excitation-Driven Hypervalent Tin(IV) Compounds For Aggregation-Induced Emission and Application to Thermoresponsive Luminescent Films below Freezing Point. 创建激发驱动的高价锡(IV)化合物，用于聚合诱导发光并将其应用于冰点以下的热致发光薄膜。

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-19 DOI: 10.1002/asia.202401094

Kazuo Tanaka, Masayuki Gon, Keisuke Shibahara, Kazuya Tanimura

Although many researchers have devoted their much effort to establish the strategy for developing a stimuli-responsive molecule and tuning of their properties according to the preprogrammed design, it is still challenging to create desired molecules from the scratch. We recently demonstrated that the molecules with a large structural difference between the theoretically optimized structures in the ground and excited states have a potential to exhibit stimuli-responsive luminescent properties. We defined these molecules as an excitation-driven molecule and have shown that they are a versatile platform for designing stimuli-responsive luminescent molecules. Herein, based on the concept of excitation-driven molecules, we show that the hypervalent tin-fused azomethine (TAm) compounds possessing aggregation-induced emission (AIE) properties can be obtained by simple chemical modification with a methyl group although conventional TAm derivatives are well known to be highly luminescent compounds in solution. Furthermore, by combining the solid-state luminescence property of AIE and the coordination number shifts of the hypervalent tin atom, the thermoresponsive films operating below the freezing point are fabricated with the polymer. In this study, we apply the concept of excitation-driven molecules to the hypervalent compounds and demonstrate to obtain the novel functional materials.

尽管许多研究人员已经投入大量精力，建立了开发刺激响应分子的策略，并根据预编程设计调整其特性，但要从零开始创造出理想的分子仍具有挑战性。我们最近证明，理论上优化的基态和激发态结构差异较大的分子有可能表现出刺激响应发光特性。我们将这些分子定义为激发驱动分子，并证明它们是设计刺激响应型发光分子的多功能平台。在此，基于激发驱动分子的概念，我们展示了具有聚集诱导发光（AIE）特性的高价锡融合偶氮亚甲基（TAm）化合物，尽管传统的 TAm 衍生物在溶液中是众所周知的高发光化合物，但通过简单的甲基化学修饰即可获得。此外，通过将 AIE 的固态发光特性与超价锡原子的配位数移动相结合，还能用聚合物制造出在冰点以下工作的热容性薄膜。在这项研究中，我们将激发驱动分子的概念应用到了超价化合物中，并展示了如何获得新型功能材料。

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引用次数: 0

Singlet Oxygen-Triggered Release of Nitric Oxide in an Endoperoxide-Arginine Conjugate 内过氧化物-精氨酸共轭物中单氧触发的一氧化氮释放

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-18 DOI: 10.1002/asia.202400759

Engin Umut Akkaya, Lei Wang, Guangyu Zhang, Yuan Qiao, Ziang Liu, Rensong Sun

Nitric oxide (NO) is an important signaling molecule in both healthy and pathological processes. In this work, we present the first example of a novel class of organic NO-donor compounds with minimal toxicity. The release is driven by the reaction of singlet oxygen spontaneously produced by the cycloreversion reaction of the endoperoxide. Cell culture and imaging data confirms the release of NO in this bimodular system.

一氧化氮（NO）是健康和病理过程中的重要信号分子。在这项工作中，我们首次展示了一类毒性极低的新型有机一氧化氮供体化合物。其释放是由内过氧化物的环氧化反应自发产生的单线态氧反应驱动的。细胞培养和成像数据证实了这种双模系统中 NO 的释放。

引用次数: 0

Catalyzing Knoevenagel Condensation and Radioiodine Sequestration with Tuned Porous Organic Polymers to Decipher the Role of Surface Area, Pore Volume, and Heteroatom 利用调谐多孔有机聚合物催化克诺文纳格尔缩合和放射性碘封存，破解表面积、孔体积和杂原子的作用

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-18 DOI: 10.1002/asia.202400969

Argha Chakraborty, Sayantan Sarkar, Ritika Munjal, Jagannath Majhi, Anasuya Bandyopadhyay, Suman Mukhopadhyay

The impact of surface area, pore volume, and heteroatom type on the performance of porous organic polymers (POPs) in various applications remains unclear. To investigate this, three isoreticular POPs were employed having one common building block, resulting in varying surface areas, pore volumes, and heteroatom compositions. This study aimed to establish a correlation between the structural features of POPs (surface area, pore volume, and heteroatom type) with their adsorption capacity, and catalytic efficiency. To explore this relationship, the Knoevenagel condensation reaction was used as a model system, testing various substituted aldehydes to further validate our findings. Additionally, the capture of radioactive iodine vapor at 75°C was simulated to examine the correlation with adsorption capacity, comparing the gravimetric iodine uptake capacity of each POP to gain insights into this relationship.

表面积、孔体积和杂原子类型对多孔有机聚合物（POPs）在各种应用中的性能的影响尚不清楚。为了研究这个问题，我们采用了三种具有一个共同结构单元的异构多孔有机聚合物，它们的表面积、孔体积和杂原子组成各不相同。本研究旨在建立持久性有机污染物的结构特征（表面积、孔体积和杂原子类型）与其吸附能力和催化效率之间的相关性。为了探究这种关系，我们使用 Knoevenagel 缩合反应作为模型系统，测试了各种取代醛，以进一步验证我们的发现。此外，我们还模拟了在 75°C 温度下捕获放射性碘蒸气的过程，以研究其与吸附能力之间的关系，并比较了每种持久性有机污染物的重量吸附碘能力，从而深入了解这种关系。

引用次数: 0

Stereoselective Electrochemical Synthesis of E‐Tetrasubstituted Haloalkenyl Chalcogenides E-Tetrasubstituted Haloalkenyl Chalcogenides 的立体选择性电化学合成

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-17 DOI: 10.1002/asia.202400960

Eric F. Lopes, Rodrigo Costa e Silva, Rafael A. C. Souza, Pablo Sebastian Fernandez, Julio Cezar Pastre

Herein, we describe an electrochemical method for the synthesis of haloalkenyl chalcogenides from internal alkynes using hydrobromic and hydrochloric acids as halogenating agents, with the sole byproduct being hydrogen gas. This e‐halochalcogenation protocol generates electrophilic chalcogenium species under mild conditions in a simple, undivided cell setup, enabling the synthesis of 25 examples of chloro‐ and bromovinyl selenides and sulfides with yields ranging from 10% to 94%, predominantly as the E‐isomer. The synthetic utility of the halovinyl chalcogenides was demonstrated through various transformations, yielding densely functionalized tetra‐substituted olefins. This underscores the versatility and efficiency of our method in assembling intricate molecular frameworks.

在此，我们介绍了一种利用氢溴酸和盐酸作为卤化剂，从内部炔烃合成卤代烯基瑀的电化学方法，唯一的副产物是氢气。这种电子卤代煅烧方案在温和的条件下，通过一个简单、未分割的电池装置生成亲电的钙鎓物种，从而合成了 25 例氯乙烯基和溴乙烯基硒化物和硫化物，产率从 10% 到 94%不等，主要是 E 异构体。卤代乙烯基卤化物的合成用途通过各种转化得到了证明，并产生了官能度极高的四取代烯烃。这凸显了我们的方法在组装复杂分子框架方面的多功能性和高效性。

引用次数: 0

4‐Halomethyl‐Substituted Imidazolium Salts: a Versatile Platform for the Synthesis of Functionalized NHC Precursors 4-Halomethyl-Substituted Imidazolium Salts：合成功能化 NHC 前体的多功能平台

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-17 DOI: 10.1002/asia.202400866

Victor Chernyshev, Dmitry V. Pasyukov, Maxim A. Shevchenko, Mikhail E. Minyaev, Valentine P. Ananikov

N,Nʹ‐Diarylimidazolium salts containing haloalkyl functional groups that are reactive with various nucleophiles are considered to be promising reagents for the preparation of functionalized N‐heterocyclic carbene (NHC) ligands, which are in demand in catalysis, materials science, and biomedical research. Recently, 4‐chloromethyl‐functionalized N,N'‐diarylimidazolium salts became readily available via the condensation of N,N'‐diaryl‐2‐methyl‐1,4‐diaza‐1,3‐butadienes with ethyl orthoformate and Me3SiCl, but these compounds were found to have insufficient reactivity in reactions with many nucleophiles. These chloromethyl salts were studied as precursors in the synthesis of bromo‐ and iodomethyl‐functionalized imidazolium salts by halide anion exchange. The 4‐ICH2‐functionalized products were found to be unstable, whereas a series of novel 4‐bromomethyl functionalized N,N'‐diarylimidazolium salts were obtained in good yields. These bromomethyl‐functionalized imidazolium salts were found to be significantly more reactive towards various N, O and S nucleophiles than the chloromethyl counterparts and enabled the preparation of previously inaccessible heteroatom‐functionalized imidazolium salts, some of which were successfully used as NHC proligands in the preparation of Pd/NHC and Au/NHC complexes.

含有卤代烷基官能团的N,Nʹ-二咪唑鎓盐可与各种亲核物反应，被认为是制备功能化N-杂环碳烯（NHC）配体的有前途的试剂，这种配体在催化、材料科学和生物医学研究中需求量很大。最近，通过 N,N'-二芳基-2-甲基-1,4-二氮杂-1,3-丁二烯与原甲酸乙酯和 Me3SiCl 的缩合，4-氯甲基官能化 N,N'-二芳基咪唑鎓盐变得很容易获得，但发现这些化合物在与许多亲核物反应时反应活性不足。研究人员将这些氯甲基盐作为前体，通过卤化阴离子交换合成溴和碘甲基官能化咪唑鎓盐。研究发现，4-ICH2 官能化产物并不稳定，而一系列新型 4-溴甲基官能化 N,N'-二芳基咪唑鎓盐的产率很高。研究发现，这些溴甲基官能化咪唑鎓盐对各种 N、O 和 S 型亲核物的反应活性明显高于氯甲基官能化咪唑鎓盐，从而制备出了以前无法获得的杂原子官能化咪唑鎓盐，其中一些还被成功用作制备 Pd/NHC 和 Au/NHC 复合物的 NHC 原配体。

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引用次数: 0

Drug Binding and Delivery with Supramolecular System Based on Sodium Carboxymethylcellulose and Viologen Calix[4]resorcinol 基于羧甲基纤维素钠和 Viologen Calix[4]resorcinol 的超分子系统的药物结合与输送技术

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-17 DOI: 10.1002/asia.202400709

Yuliya Razuvayeva, Ruslan Kashapov, Albina Ziganshina, Vadim Salnikov, Anastasiia Sapunova, Alexandra Voloshina, Lucia Zakharova

In the present work, a simple supramolecular approach was used to spontaneously form nanoparticles from sodium carboxymethylcellulose and viologen calix[4]resorcinol as a result of joint self‐assembly in water at room temperature. Supramolecular interactions between them led to the formation of nanoparticles, the morphology and properties of which depend on polymer/macrocycle ratio. When there is excess of macrocycle, the nanoparticles bind lipophilic oleic acid, and when there is excess of polymer, they bind hydrophilic doxorubicin. Interestingly, the solubilization of lipophilic quercetin into these nanoparticles was significantly increased compared to the pure polymer and macrocycle, regardless of their ratio. The nanoparticles of triple composition (polymer/macrocycle/drug) have a more effective penetration ability into these cells than those of double composition (polymer/drug). The presented results are the first step towards the creation of new nanotechnologies to improve the bioavailability and delivery of bioactive components.

本研究采用一种简单的超分子方法，使羧甲基纤维素钠和紫罗兰钙[4]间苯二酚在室温水中通过联合自组装自发形成纳米颗粒。它们之间的超分子相互作用导致了纳米颗粒的形成，其形态和性质取决于聚合物/大环的比例。当大环过量时，纳米颗粒与亲脂性油酸结合，而当聚合物过量时，则与亲水性多柔比星结合。有趣的是，与纯聚合物和大环相比，无论它们的比例如何，亲脂性槲皮素在这些纳米颗粒中的溶解度都显著增加。三重成分（聚合物/大环/药物）的纳米颗粒比双重成分（聚合物/药物）的纳米颗粒对这些细胞的渗透能力更强。这些研究成果为开发新的纳米技术，提高生物活性成分的生物利用率和输送能力迈出了第一步。

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引用次数: 0

Front Cover: Photoacoustic Imaging Using Polysaccharide-Porphyrin Complexes by Photoirradiation at Long Wavelengths (Chem. Asian J. 18/2024) 封面：通过长波长光照射使用多糖-卟啉复合物进行光声成像（《亚洲化学杂志》18/2024）

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-16 DOI: 10.1002/asia.202481801

Seiya Fujita, Riku Omokawa, Dr. Keita Yamana, Dr. Riku Kawasaki, Dr. Risako Miura, Prof. Teruyuki Kondo, Prof. Atsushi Ikeda

The superior PA imaging intensity of a λ-carrageenan (CGN)–5,10,15,20-tetrakis(4-aminophenyl)porphyrin (Por) complex was observed to the retention of the porphyrin within CGN and its increased absorbance in the 680–800-nm range at pH 5.0. These findings highlight the potential of in CGN–Por as a theranostic agent for combined photodynamic therapy and PA imaging diagnostics in cancer treatment. More details can be found in article number e202400571 by Risako Miura, Atsushi Ikeda, and co-workers.

据观察，λ-卡拉胶（CGN）-5,10,15,20-四(4-氨基苯基)卟啉（Por）复合物的PA成像强度较高，这是因为卟啉保留在CGN中，而且在pH值为5.0时，CGN在680-800纳米范围内的吸光度增加。这些发现凸显了 CGN-Por 作为一种治疗剂在癌症治疗中结合光动力疗法和 PA 成像诊断的潜力。更多详情请见 Risako Miura、Atsushi Ikeda 及合作者撰写的 e202400571 号文章。

引用次数: 0

Primordial Molecular 1-Bit Magnitude Comparator in consort with Excitation-Guided mouldable Logic Systems: A guided design of Regular Interactions between Molecules 原始分子 1 位振幅比较器与激发引导的可塑逻辑系统：分子间常规相互作用的引导设计

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-16 DOI: 10.1002/asia.202400843

Monaj Karar, Suraj Pise, Nilanjan Dey

In addition to designing certain excitation modulated logic systems, we have created the first-ever genuine molecular 1-bit magnitude comparator, using acid and base guided varied absorption responses at separate channels. Designed and manufactured Bifunctional Bis(indolyl)methane Derivative (1) demonstrates distinct optical responses (in UV-visible and fluorescence mode) to a range of chemical stimuli (acid, base, Hg2+, Cu2+, EDTA, GSH, etc.) in aqueous medium. Intriguingly, the compound's excitation-modulated fluorescence responses appeared to change at different detection channels depending on whether the aforementioned analytes were present or not. We have proposed not only an excitation driven logic system with switchable molecular IMPLICATION and XNOR logic gates, but also a molecular 1-bit magnitude comparator in our proposal. A second excitation driven logic system with switchable molecular COMPLEMENT and NOR logic gates was also designed with two different optical channels and used Hg(II) & Cu(II) as chemical inputs.

除了设计某些激发调制逻辑系统外，我们还利用酸和碱在不同通道上引导的不同吸收反应，创造了有史以来第一个真正的分子 1 位幅度比较器。设计和制造的双功能双（吲哚基）甲烷衍生物 (1) 在水介质中对一系列化学刺激（酸、碱、Hg2+、Cu2+、EDTA、GSH 等）表现出独特的光学响应（紫外可见光和荧光模式）。有趣的是，根据上述分析物的存在与否，该化合物的激发-调制荧光反应似乎在不同的检测通道发生了变化。我们不仅提出了一个具有可切换的分子 IMPLICATION 逻辑门和 XNOR 逻辑门的激发驱动逻辑系统，还提出了一个分子 1 位幅度比较器。我们还设计了带有可切换分子 COMPLEMENT 和 NOR 逻辑门的第二个激发驱动逻辑系统，该系统有两个不同的光学通道，使用 Hg(II) & Cu(II) 作为化学输入。

引用次数: 0

Isostructural Oxamate Complexes with Visible Luminescence (Eu3+) and Field-Induced Single-Molecule Magnet (Nd3+) 具有可见发光（Eu3+）和场诱导单分子磁性（Nd3+）的异构草氨酸配合物

IF 4.568 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal

Pub Date : 2024-09-16 DOI: 10.1002/asia.202400887

Emilay B.T. Diogo, Eufrânio N. da Silva Júnior, Willian X. C. Oliveira, Humberto O. Stumpf, Fernando Fabris, Adriele A. de Almeida, Marcelo Knobel, Fabio F. Ferreira, Wallace C. Nunes, Emerson F. Pedroso, Miguel Julve, Cynthia L. M. Pereira

The search for new metal-organic compounds as candidates for quantum information processing technologies is in the spotlight. Several metal ions and organic linkers have been used to obtain such compounds. Herein, we describe the synthesis, crystal structures, and cryomagnetic properties of two air-stable isostructural neodymium(III) and europium(III) one-dimensional (1D) coordination polymers of formula [Nd(Hmpa)3(DMSO)2]n (1) and [Eu(Hmpa)3(DMSO)2]n (2) [Hmpa = N-(4-methylphenyl)oxamate, and DMSO = dimethylsulfoxide]. These complexes were prepared by reacting n-Bu4N(Hmpa) proligand [n-Bu4N+ = tetra-n-butylammonium] and the correspondent LnCl3·6H2O salt (Ln = Nd or Eu) in the open air and mild conditions. The crystal structures of 1 and 2 reveal the Ln3+ ion surrounded by two DMSO molecules and three oxamate ligands, one of them connecting to adjacent mononuclear entities through carboxylate bridges featuring a 1D coordination polymer, while the other two establishing double N–H···O hydrogen bonds among adjacent polymers to give a resultant supramolecular 2D network. Cryomagnetic measurements in the static (dc) and dynamic current (ac) regimes reveal that 1 behaves as a field-induced single-molecule magnet below 8.8 K. A photoluminescence study shows that Hmpa ligands efficiently sensitize the luminescence of Eu3+ complex in the visible region in the solid state at room temperature.

寻找新的金属有机化合物作为量子信息处理技术的候选材料，是目前的焦点。一些金属离子和有机连接体已被用于获得此类化合物。在此，我们介绍了两种空气稳定的等结构钕（III）和铕（III）一维（1D）配位聚合物的合成、晶体结构和低温磁性能，它们的化学式分别为[Nd(Hmpa)3(DMSO)2]n (1)和[Eu(Hmpa)3(DMSO)2]n (2)[Hmpa=N-(4-甲基苯基)草氨酸，DMSO=二甲基亚砜]。这些配合物是由 n-Bu4N(Hmpa)原配体[n-Bu4N+ = 四正丁基铵]和相应的 LnCl3-6H2O 盐（Ln = Nd 或 Eu）在露天温和条件下反应制备的。1 和 2 的晶体结构显示，Ln3+ 离子被两个二甲基亚砜分子和三个草氨酸配体包围，其中一个配体通过羧酸桥与相邻的单核实体连接，形成一维配位聚合物，而另外两个配体则在相邻聚合物之间建立双 N-H-O 氢键，形成超分子二维网络。在静态（直流）和动态电流（交流）状态下进行的低温磁性测量显示，1 在 8.8 K 以下表现为场诱导的单分子磁体。光致发光研究显示，Hmpa 配体在室温固态下有效地敏化了 Eu3+ 复合物在可见光区域的发光。

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