Asian Journal of Organic Chemistry最新文献

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Direct In Situ Polymer Modification of Titania Nanomaterial Surfaces via UV‐irradiated Radical Polymerization 通过紫外线辐射辐射聚合对二氧化钛纳米材料表面进行直接原位聚合物改性

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400270

Polymer modification of titania nanomaterials can provide media dispersibility and various functionalities onto the titania surface. Herein, we report the direct in situ polymer modification of the surface of titania nanotubes (TNTs) and titania nanoparticles (TNPs) via ultraviolet (UV)‐irradiated radical polymerization without any pretreatment of titania. The resulting polymer‐modified TNTs and TNPs dispersed well in solvents. The characterization of the products using various techniques including Fourier transform infrared spectroscopy, thermogravimetric analysis, and scanning electron microscopy‐energy dispersive X‐ray spectroscopy confirmed the successful modification of the TNT and TNP surfaces by the polymers produced via UV‐irradiated radical polymerization. The polymers on the titania surface were isolated by dissolving titania using hydrofluoric acid and analyzed by means of size exclusion chromatography and matrix‐assisted laser desorption/ionization‐time of flight‐mass spectrometry. The polymer‐modified TNTs and TNPs maintained their photocatalytic activity in dye degradation under UV irradiation. Moreover, glycopolymer‐modified TNTs were successfully prepared using the UV‐irradiated polymerization system. The glycopolymer retained its lectin biding affinity on the TNT surface.

对二氧化钛纳米材料进行聚合物改性可在二氧化钛表面提供介质分散性和各种功能。在此，我们报告了在不对二氧化钛进行任何预处理的情况下，通过紫外线（UV）辐照自由基聚合对二氧化钛纳米管（TNTs）和二氧化钛纳米颗粒（TNPs）表面进行直接原位聚合物改性的方法。所得到的聚合物改性 TNTs 和 TNPs 在溶剂中分散良好。利用傅立叶变换红外光谱、热重分析和扫描电子显微镜-能量色散 X 射线光谱等多种技术对产品进行的表征证实，通过紫外光照射自由基聚合产生的聚合物成功地改性了 TNT 和 TNP 的表面。使用氢氟酸溶解二氧化钛，分离出二氧化钛表面的聚合物，并通过尺寸排阻色谱法和基质辅助激光解吸/电离飞行时间质谱法进行分析。在紫外线照射下，聚合物改性的 TNTs 和 TNPs 在降解染料方面保持了光催化活性。此外，利用紫外辐照聚合体系还成功制备了糖聚合物改性 TNTs。糖聚合物在 TNT 表面保持了凝集素的亲和性。

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引用次数: 0

Current Developments in Michael Addition Reaction using Heterocycles as Convenient Michael Donors 利用杂环作为方便的迈克尔供体进行迈克尔加成反应的最新进展

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400193

The Michael addition reaction, a cornerstone of contemporary organic synthesis, has witnessed a resurgence of interest owing to its ability to forge intricate carbon‐carbon and carbon‐heteroatom bonds. In the past few years, heterocyclic compounds have been rigorously used as Michael donors, owing to their architectural diversity and distinct reactivity with or without the presence of base/transition metals/organocatalysts. This review encapsulates the latest breakthroughs in chemistry involving Michael addition reaction using heterocyclic compounds as Michael donors. It delivers a comprehensive update on developments in Michael addition reaction triggered by potent heterocycles since 2017, highlighting novel and innovative methodologies, with strategic insights.

迈克尔加成反应是当代有机合成的基石，由于它能够形成复杂的碳-碳键和碳-异原子键，因此再次引起了人们的兴趣。在过去几年中，杂环化合物因其结构的多样性和独特的反应活性，无论是否存在碱/过渡金属/有机催化剂，都被严格用作迈克尔供体。本综述囊括了以杂环化合物为迈克尔供体进行迈克尔加成反应的最新化学突破。它全面介绍了 2017 年以来由强效杂环引发的迈克尔加成反应的最新进展，重点介绍了新颖和创新的方法，并提出了战略性见解。

引用次数: 0

Dinitropyridines: Synthesis and Reactions 二硝基吡啶：合成与反应

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400304

Dinitropyridines are one of the promising classes of heterocyclic compounds. They are considered as useful precursors of explosives and energetic compounds, agrochemicals, biosensors and biologically active compounds with diverse properties: antitumor, antiviral, anti‐neurodegenerative. Preliminary analysis of literature data shows that the chemistry of polynitropyridines has been actively developing over the past few decades. This is evidenced by the steadily growing annual number of publications. In this review the literature on the synthesis, reactions and practical application of isomeric dinitropyridines over a period of 2010–2024 is analyzed.

二硝基吡啶是一类前景广阔的杂环化合物。它们被认为是炸药、高能化合物、农用化学品、生物传感器和生物活性化合物的有用前体，具有多种特性：抗肿瘤、抗病毒、抗神经退行性病变。对文献数据的初步分析表明，在过去几十年中，多硝基吡啶化学一直在积极发展。每年发表的论文数量稳步增长就证明了这一点。本综述分析了 2010-2024 年间有关异构二硝基吡啶的合成、反应和实际应用的文献。

引用次数: 0

Synthesis and Performance of Bithiophene Isoindigo Organic Semiconductors with Side‐Chain Functionality in Transistors 晶体管中具有侧链功能的噻吩异靛蓝有机半导体的合成与性能

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400250

The isoindigo and its derivatives have rapidly garnered attention as widely employed electron‐deficient moieties, finding extensive applications in organic field‐effect transistors. In this study, four different isoindigo‐based organic semiconductor polymers were synthesized via a Stille coupling reaction of four isoindigo molecules with varying side chains serving as acceptors and bithiophene as donors. Furthermore, their optical, electrochemical, thermal stability, and other relevant properties were comprehensively evaluated. These polymers exhibited remarkable electrochemical and thermal stability attributed to their low LUMO energy level, which facilitates effective electrical contact between the semiconductor layer and the source/drain while ensuring excellent air stability for the semiconductor polymers. Additionally, solution‐gate field‐effect transistors prepared using these polymers achieved hole mobilities of 10⁻² cm² V⁻¹ S⁻¹ along with an I_on/I_off ratio of 8.39×10³, demonstrating exceptional field‐effect performance.

异靛蓝及其衍生物作为广泛应用的缺电子分子，在有机场效应晶体管中得到了广泛的应用，并迅速引起了人们的关注。本研究通过四种不同侧链的异靛蓝分子作为受体和噻吩作为供体的 Stille 偶联反应，合成了四种不同的异靛蓝基有机半导体聚合物。此外，还对它们的光学、电化学、热稳定性和其他相关特性进行了全面评估。这些聚合物的 LUMO 能级较低，有利于半导体层与源极/漏极之间的有效电接触，同时确保了半导体聚合物在空气中的出色稳定性，因此表现出了出色的电化学和热稳定性。此外，利用这些聚合物制备的溶液栅场效应晶体管的空穴迁移率达到了 10-2 cm2V-1S-1，离子/间隙比为 8.39×103，显示出卓越的场效应性能。

引用次数: 0

Phenylboronic Acid‐Functionalized Hyaluronic Acid as Polysaccharide Carriers for Diol‐Containing Drugs Delivery 苯基硼酸官能化透明质酸作为多糖载体用于含二醇药物的输送

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400182

Packaging hydrophobic drugs into polysaccharide carriers can improve their aqueous solubility, biocompatibility, tumor‐specific accumulation, and therapeutic effect. In this work, phenylboronic acid (PBA) was anchored onto the chain of biocompatible polysaccharide hyaluronic acid (HA) by an amide condensation reaction, which could be used to fabricate stimuli‐responsive targeted drug delivery systems. A series of pH‐responsive conjugated hyaluronic acid nanoparticles composed of a hydrophobic drug core and hydrophilic hyaluronic acid shell were prepared by the boronate‐crosslink of the PBA with diol‐containing anticancer drugs such as capecitabine (CAPE) and aloin (Al). Satisfactory targeted drug release behavior at acidic pH, lower cytotoxicity, and higher anticancer effect were realized by using this polysaccharide carrier. It is believed that this strategy has great potential for polysaccharide modification and anticancer‐associated applications.

将疏水性药物封装到多糖载体中可提高其水溶性、生物相容性、肿瘤特异性蓄积和治疗效果。本研究通过酰胺缩合反应将苯硼酸（PBA）锚定在生物相容性多糖透明质酸（HA）的链上，从而制备出刺激响应型靶向给药系统。通过硼酸盐交联 PBA 与卡培他滨（CAPE）和阿糖胞苷（Al）等含二元醇的抗癌药物，制备了一系列由疏水性药物核心和亲水性透明质酸外壳组成的 pH 响应型共轭透明质酸纳米粒子。通过使用这种多糖载体，在酸性 pH 条件下实现了令人满意的靶向药物释放行为，降低了细胞毒性，提高了抗癌效果。相信这一策略在多糖改性和抗癌相关应用方面具有巨大潜力。

引用次数: 0

Advances in the Synthesis of 1,3‐Disubstituted Ferrocene Derivatives: From Stoichiometric to Catalytic Methods 1,3-二取代二茂铁衍生物的合成进展：从计量方法到催化方法

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400301

Functionalized ferrocene derivatives have a wide range of applications across various scientific fields. Although significant progress has been made in synthesizing 1,2‐disubstituted ferrocene derivatives, the preparation of 1,3‐disubstituted ferrocenes remains challenging. Recently, however, several powerful synthetic approaches to 1,3‐disubstituted ferrocenes have been reported. This review aims to present the evolution of these synthetic methods, from initial stoichiometric approaches to the more recent catalytic methodologies.

功能化二茂铁衍生物在各个科学领域都有广泛的应用。尽管在合成 1,2-二茂铁衍生物方面取得了重大进展，但 1,3-二茂铁的制备仍然具有挑战性。不过，最近有报道称，1,3-二取代二茂铁有几种强大的合成方法。本综述旨在介绍这些合成方法的演变，从最初的化学计量学方法到最近的催化方法。

引用次数: 0

Synthesis of 1,2,3-Triphospholenes, 1,2-Diphosphetes, and Unsymmetric Phospholes by Rhodium-catalyzed Cleavage of P–P Bonds and Addition to Alkynes 通过铑催化的 P-P 键裂解和与炔烃的加成合成 1,2,3-三磷烯、1,2-二磷烯和不对称磷烯

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-09-20 DOI: 10.1002/ajoc.202400376

Mieko Arisawa, Hiiro Otsuka, Tomoko Idogawa, Kyosuke Sawahata, Yasutaka Kawai

The rhodium-catalyzed addition reaction of cyclo-(PPh)5 to alkynes in refluxing THF efficiently provide 1,2,3-triphospholenes, in which the –PPh–PPh–PPh– group is transferred from cyclo-(PPh)5 by the cleavage of P–P bonds. In refluxing chlorobenzene, the reactions are accompanied by the formation of 1,2-diphosphetes. When the triphospholenes containing P–P bonds are reacted with reactive alkynes under rhodium-catalyzed conditions, unsymmetric phospholes are obtained. The rhodium-catalyzed reactions can be used to synthesize various phosphorus-containing heterocycles with different numbers of phosphorus atoms.

在回流四氢呋喃中，铑催化的环-(PPh)5 与炔烃的加成反应可有效地生成 1,2,3-三膦烯，其中 -PPh-PPh-PPh- 基团通过 P-P 键的裂解从环-(PPh)5 中转移出来。在回流氯苯中，反应伴随着 1,2-二磷酸盐的形成。当含有 P-P 键的三磷烯在铑催化条件下与活性炔烃反应时，会得到不对称的磷烯。铑催化反应可用于合成具有不同磷原子数的各种含磷杂环。

引用次数: 0

Facile Synthesis of Diverse 1,3,5-Trisubstituted 1,2,4-Triazole using Hydrazones with Aldehydes, Alkenes, Amines 使用肼酮与醛类、烯类和胺类轻松合成多种 1,3,5-三取代的 1,2,4- 三唑

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-09-18 DOI: 10.1002/ajoc.202400424

Yi Liu, Kunyi Zhang, Jialiang Zhang, Shuaikun Liu, Yu Song, Xinqiang Tan, Lizhen Fang

An efficient, and easy method for the synthesis of 1,3,5- substituted 1,2,4-triazole derivatives by [3+2] annulation reactions of hydrazones with aldehydes, alkenes, or amines has been established. This strategy is characterized by the use of inexpensive and readily available oxidants and starting materials, a broader substrate scope, and moderate to good yields.

通过肼与醛、烯或胺的[3+2]环化反应合成 1,3,5-取代的 1,2,4-三唑衍生物的高效简便方法已经建立。这种策略的特点是使用廉价易得的氧化剂和起始原料，底物范围更广，收率适中甚至很高。

引用次数: 0

Stereoselective Synthesis of AB-5,15-Porphyrinquinone Platinum(II) Complexes 立体选择性合成 AB-5,15-卟啉醌铂(II)配合物

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-09-18 DOI: 10.1002/ajoc.202400375

Ryo Inoue, Iori Yamada, Momoka Yokoyama, Yasuhiro Morisaki

5,15-Porphyrinquinone is a non-aromatic and electron-deficient porphyrinoid that acts as an important framework for the synthesis of porphyrinoid derivatives. Generally, meso-functionalized A2-porphyrinquinone is synthesized via the oxidation of A2-porphyrin. Herein, we present the stereoselective synthesis of AB-porphyrinquinone Pt(II) complexes using the corresponding dipyrrinato-Pt complexes and bisformyldipyrrins. The reaction involves cyclization and oxidative aromatization induced by the Pt template, followed by oxidation using a mild MnO2 oxidant.

5,15-卟啉醌是一种非芳香族的缺电子卟啉类化合物，是合成卟啉衍生物的重要框架。一般来说，中官能化 A2-卟啉醌是通过氧化 A2-卟啉合成的。在这里，我们利用相应的二吡咯烷铂络合物和双甲酰基二吡咯啉，立体选择性地合成了 AB-卟啉醌铂(II)络合物。反应包括铂模板诱导的环化和氧化芳香化，然后使用温和的 MnO2 氧化剂进行氧化。

引用次数: 0

Photoswitchable AIE-Active Supramolecular Self-Assemblies for Biosensing and Bioimaging 用于生物传感和生物成像的光开关 AIE 活性超分子自组装体

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-09-18 DOI: 10.1002/ajoc.202400385

Fengfan Zhu, Xiao-Fang Hou, Juping Wang, Lei Bi, Jiancheng Zhou, Xu-Man Chen

Photoswitchable fluorescent self-assemblies exhibiting aggregation-induced emission (AIE) properties have garnered widespread attention. Due to their great adaptiveness and responsiveness towards different wavelengths required by photoreaction, photo-isomerization, and photoluminescence excitation, these fluorescent self-assemblies show diverse emission behavior in a spatial, temporal, and polychromatic manner. Integrating organic photoswitches and AIE fluorophores, these photoluminescent nano-assemblies has been proven to be an effective approach, allowing the development of sophisticated systems for drug release and cell regulation that can be precisely manipulated through light or other stimuli. This review systematically encapsulates recent advances in photoswitchable fluorescent self-assemblies under multi-scenario biological applications. The construction of photoswitchable AIE fluorophores through covalent and non-covalent interactions and their multimodal regulation are detailed, along with their biological applications in biosensing, bioimaging, and drug therapy.

表现出聚集诱导发射（AIE）特性的可光开关荧光自组装体引起了广泛关注。由于对光反应、光异构化和光致发光激发所需的不同波长具有很强的适应性和响应性，这些荧光自组装体在空间、时间和多色性方面表现出多种发射行为。将有机光开关和 AIE 荧光团整合在一起，这些光致发光纳米组合体已被证明是一种有效的方法，可用于开发复杂的药物释放和细胞调控系统，并可通过光或其他刺激进行精确操控。这篇综述系统地总结了在多场景生物应用下可光电开关荧光自组装的最新进展。详细介绍了通过共价和非共价相互作用构建光开关 AIE 荧光团及其多模式调控，以及它们在生物传感、生物成像和药物治疗方面的生物学应用。

引用次数: 0

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