Article
Chemistry, Organic
Andrey Bubyrev, Ksenia Malkova, Grigory Kantin, Dmitry Dar'in, Mikhail Krasavin
Summary: A three-component synthesis of 1,5-disubstituted 1,2,3-triazoles can be achieved from alpha-acetyl-alpha-diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes. The synthesis can proceed in two alternative variants based on the substitutions in the diazo reagent. Depending on the variant, the intermediates are either isolated and subjected to aromatization, or both transformations take place in a single step at room temperature.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Tomas Opsomer, Wim Dehaen
Summary: This article provides an overview of the latest developments in metal-free synthesis of non-benzo-fused N-functionalized and NH-1,2,3-triazoles, including oxidative and eliminative azide-dipolarophile cycloadditions, diazo transfer reactions, and N-tosylhydrazone-mediated syntheses. These newly developed methods have significantly contributed to the field of 1,2,3-triazole synthesis by exploring novel reactions and utilizing existing methodologies for structural variation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Mohammad Sadegh Asgari, Saeed Bahadorikhalili, Aram Ghaempanah, Parviz Rashidi Ranjbar, Rahmatollah Rahimi, Alireza Abbasi, Bagher Larijani, Mohammad Mahdavi
Summary: In this study, novel amide linked 1,2,3-triazoles containing aryloxy derivatives were synthesized efficiently via copper-catalyzed one-pot sequential reaction, with high isolated yields.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Tayyala Kiranmye, Murugan Vadivelu, Sugirdha Sampath, Kesavan Muthu, Kesavan Karthikeyan
Summary: This strategy for the synthesis of 1-substituted-4-acyl-1,2,3-triazoles and 1,5-disubstituted-1,2,3-triazoles via eliminative [3 + 2] cycloaddition of azides with beta-enaminones/nitroolefins is catalyst free and utilizes ultrasound irradiation, offering features such as broad substrate scope, short reaction time, simple work-up, high regioselectivity and suitability for large-scale synthesis.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Organic
Cong Dong, Shaoyu Mai, Shuai Wang, Xin Li, Qiuling Song
Summary: A sustainable intramolecular reaction strategy using alkali-promoted, transition-metal-free and oxidant-free method has been developed for the construction of 4,5-disubstituted-1,2,3-thiadiazoles from N-tosylhydrazone-bearing thiocarbamates. This method shows high efficiency, good functional group compatibility, readily available starting materials, and valuable products. It has great potential in the synthesis of natural products, pharmaceuticals, and materials.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Atul Kumar, Navaneet Kumar, Deepak Bhadoria
Summary: The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to efficiently synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. This reaction offers high regioselectivity, scalability, and good functional group tolerance among its advantages.
Article
Chemistry, Organic
R. Rengasamy, K. Vijayalakshmi, N. Punitha, J. Paul Raj, K. Karthikeyan, J. Elangovan
Summary: A collection of 1,4-disubstituted 1,2,3-triazoles was synthesized via decarboxylative [3 + 2] cycloaddition of organic azides and cinnamic acids. The protocol features metal-free conditions, high regioselectivity, and easy accessibility of starting materials.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Ranadeep Talukdar, Vikram Singh, Hemlata Mourya, Malik Nasibullah, Bhoopendra Tiwari
Summary: The new method reported in this study synthesizes 1,2,3-triazole-fused polyaromatic frameworks through a three-step reaction. Under mild conditions, the target products are obtained, along with the corresponding dihydrocarbocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ksenia Malkova, Andrey Bubyrev, Saeed Balalaie, Dmitry Dar'in, Mikhail Krasavin
Summary: This Digest Article reviews the recently emerged metal-free methods for synthesizing 1,5-disubstituted 1,2,3-triazoles, which show great potential compared to traditional metal-catalyzed methods.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Shanguang Qiu, Yuxue Chen, Xinming Song, Li Liu, Xi Liu, Luyong Wu
Summary: In this study, intermolecular cycloaddition of tosylhydrazones with nitriles was investigated. t-BuOK was found to be an excellent base for increasing reaction effectiveness, while using xylene as a solvent significantly inhibited homocoupling of the tosylhydrazones. As a result, a variety of 4,5-diaryl-2H-1,2,3-triazoles were prepared in good to excellent yields and high purities, with the process being azide-free and transition-metal-free.
Article
Chemistry, Multidisciplinary
Vladimir Motornov, Petr Beier
Summary: An efficient one-pot method has been developed for the synthesis of 2-fluoroalkyloxazoles. This method offers a mild and high-yielding approach to prepare structurally diverse fluoroalkylated oxazoles from readily available starting reagents. Furthermore, an alternative direct method using acetonitrile as the solvent has been described for the synthesis of fluoroalkylated oxazoles from electron-rich NH-triazoles.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Kotaro Ishihara, Kazuki Ishihara, Yamato Kato, Shota Shibuya, Takayuki Shioiri, Masato Matsugi
Summary: In this study, 4-aryl-NH-1,2,3-triazoles were efficiently synthesized from benzyl-type ketones using diphenyl phosphorazidate (DPPA) and 1,8-diazabicyclo[5.4.0]undec-7-ene under solvent-free conditions. This method offers a rapid and non-toxic alternative for the preparation of NH-1,2,3-triazoles.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Wan-Yu Chen, Wei-Han Lin, Chia-Jou Kuo, Chien-Fu Liang
Summary: N-Sulfonylthioimidate is converted to ketenimine under basic conditions. The reaction with vinyl/aryl azides induces dipolar cycloaddition to form 5-amino-1-vinyl/aryl-1,2,3-triazoles. The method boasts high efficiency, diverse product structures, favorable yields, and applicability to gram-scale operations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Dominik Jankovi, Miha Virant, Martin Gazvoda
Summary: In this study, we report a sustainable copper-catalyzed reaction that forms 4-substituted-1H-1,2,3-triazoles through a cycloaddition of hydrogen azide with terminal alkynes. The reaction proceeds under mild conditions, using polydentate N-donor chelating ligands and mild organic acids. High yields of the desired triazoles are achieved with low catalyst loadings. This method shows excellent functional group tolerance and is applicable for late-stage functionalization in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Leiyang Lv, Ge Gao, Yani Luo, Kuantao Mao, Zhiping Li
Summary: The study developed a three-component assembly method under transition-metal-free and open-air conditions for the construction of various 5-amino NH-1,2,3-triazoles, offering a simple and widely applicable approach. It was also demonstrated that NH-1,2,3-triazoles can be smoothly converted to regiospecific N-2 alkylated 1,2,3-triazole products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiaohui Chen, Niu Niu, Dan Li, Zicong Zhang, Zeyan Zhuang, Dingyuan Yan, Jiangao Li, Zujin Zhao, Dong Wang, Ben Zhong Tang
Summary: Through molecular engineering, an optimized photoactivatable agent, TPA-DHPy-Py, with low oxidation potential, high photoactivation efficiency, and excellent type I/II combined photodynamic activity has been developed. It is capable of precisely identifying cancer cells, monitoring intracellular lipid droplets and endoplasmic reticulum alterations, and achieving highly contrasted fluorescent visualization of tumors in vivo. Furthermore, it demonstrates significant inhibition of tumor growth, showcasing its unprecedented performance in photodynamic cancer therapy.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Review
Chemistry, Multidisciplinary
Haoxuan Li, Bingqi Jin, Yuanwei Wang, Bingyao Deng, Dong Wang, Ben Zhong Tang
Summary: Aggregation-induced emission luminogens (AIEgens) have made rapid progress in the field of organic luminescent materials due to their superior properties, yet the transformation of AIEgens from molecules to materials remains a challenge. Integration of AIEgens into fiber has been achieved, resulting in fiber with prominent fluorescence and/or photosensitizing capacities. AIEgens and fiber complement each other in flexible smart materials, opening new application possibilities for fiber and providing an ideal platform for studying the aggregate state of AIEgens.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Junyao Xie, Niu Niu, Xinyao Fu, Xiang Su, Dong Wang, Anjun Qin, Ting Han, Ben Zhong Tang
Summary: The development of facile polymerizations is important for the synthesis of functional heterocyclic polymers. In this study, a catalyst-free multicomponent polymerization method was used to synthesize functional polyoxadiazoles (PODs) with well-defined and diversified topological structures. The obtained PODs possess good solubility, high thermal and morphological stability, and excellent film-forming ability. The introduction of aggregation-induced emission (AIE) moieties enables these polymers to be used as promising lysosome-specific fluorescent probes in biological imaging.
Article
Chemistry, Multidisciplinary
Jianxing Wang, Jie Li, Zipeng Shen, Dong Wang, Ben Zhong Tang
Summary: In this study, phospholipid-mimetic aggregation induced emission luminogens (AIEgens) were developed to selectively eliminate both Gram-positive and Gram-negative bacteria. By utilizing the different structure of two bacterial membranes and the regulated length of substituted alkyl chains of AIEgens, these AIEgens can anchor onto the bacterial membrane and kill bacteria. AIEgens with short alkyl chains exhibit selective ablation to Gram-positive bacteria, while AIEgens with long alkyl chains selectively destroy the membranes of Gram-negative bacteria. Fluorescent imaging and in vitro/in vivo experiments confirm the extraordinary antibacterial selectivity of these AIEgens towards both types of bacteria. This research could contribute to the development of species-specific antibacterial agents.
Article
Chemistry, Multidisciplinary
Bin Li, Wei Wang, Lu Zhao, Dingyuan Yan, Xiaoxue Li, Qiuxia Gao, Judun Zheng, Sitong Zhou, Shanshan Lai, Yi Feng, Jie Zhang, Hang Jiang, Chengmin Long, Wenjun Gan, Xiaodong Chen, Dong Wang, Ben Zhong Tang, Yuhui Liao
Summary: The inappropriate use of antibiotics has caused the rise of drug-resistant bacteria, posing a significant threat to global health. Researchers have developed a self-assembled aggregation-induced emission (AIE) nanosphere with near-infrared region II (NIR-II) fluorescence, photothermal, and photodynamic properties for the theranostics of drug-resistant bacterial infections. The nanosphere, encapsulated with teicoplanin and ammonium bicarbonate, forms a laser-activated nanobomb that enables multimodal imaging and synergistic therapeutic effects on multidrug-resistant bacteria strains.
Article
Chemistry, Multidisciplinary
Haitao Hu, Dan Li, Wenbin Dai, Qiao Jin, Dong Wang, Jian Ji, Ben Zhong Tang, Zhe Tang
Summary: Compared to conventional PTT, mild-temperature PTT is a more promising antitumor strategy with lower phototoxicity. However, the thermoresistance of cancer cells limits its efficacy. In this study, a supramolecular nanocarrier is developed to co-deliver NO and DCTBT for mild-temperature PTT. The generated ONOO- can enhance the therapeutic efficacy by reducing the thermoresistance of cancer cells. The antitumor performance of this strategy is validated on HCC models.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Jie Cui, Fei Zhang, Dingyuan Yan, Ting Han, Lei Wang, Dong Wang, Ben Zhong Tang
Summary: This study successfully developed a versatile molecule DHTDP with aggregation-induced emission, which can simultaneously exhibit second near-infrared (NIR-II) fluorescence emission and efficient photothermal conversion. By camouflaging DHTDP nanoparticles with cancer cell membrane, the resultant biomimetic nanoparticles not only have facilitated delivery efficiency and homologous targeting capability, but also provide precise imaging guidance through NIR-II fluorescence imaging, photoacoustic imaging, and photothermal imaging. This study presents a new approach to explore superior phototheranostics for practical cancer theranostics using biomimetic multimodal phototheranostics loaded by homogeneity-targeting cell membrane.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Runfeng Lin, Junkai Liu, Weilin Xu, Zicheng Liu, Xiang He, Canze Zheng, Miaomiao Kang, Xue Li, Zhijun Zhang, Hai-Tao Feng, Jacky W. Y. Lam, Dong Wang, Ming Chen, Ben Zhong Tang
Summary: In this work, a pyrazine-based near-infrared type I photosensitizer (PS) with remarkable donor-acceptor effect and efficient intramolecular motions was developed. The PS exhibited high photothermal conversion efficiency and strong hydroxyl radical generation due to its vigorous intramolecular motions. It also demonstrated excellent imaging-guided cancer synergistic therapy, stimulating the development of advanced PS and solid-state intramolecular motions for biomedical applications.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Jiangao Li, Miaomiao Kang, Zhijun Zhang, Xue Li, Weilin Xu, Dong Wang, Xike Gao, Ben Zhong Tang
Summary: In this study, a precise dual-acceptor engineering strategy is used to integrate ultralong excitation wavelength, high extinction coefficient, and prominent photothermal conversion ability into a single photothermal agent. The optimized polymer SP4 shows desirable second near-infrared (NIR-II) absorption, an extremely high extinction coefficient, and satisfactory photothermal conversion behavior. SP4 NPs demonstrate unprecedented performance in 1064 nm laser-excited photoacoustic imaging (PAI)-guided photothermal therapy (PTT), enabling precise tumor diagnosis and complete tumor elimination.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yufeng Xiao, Kaibo Zheng, Nuonuo Zhang, Yanlan Wang, Jiaying Yan, Dong Wang, Xiang Liu
Summary: Although progress has been made in the design and development of mono-shift mechanofluorochromic materials, it remains challenging to explore materials with opposite mechanofluorochromic behavior. In this study, two unprecedented fluorophores (X-1 and X-2) were designed and synthesized, and they exhibit completely opposite mechanofluorochromism. The opposite behavior is attributed to the transformation of order-crystalline and amorphous states, which is further explained by the pi-extended systems. Moreover, these fluorophores show excellent compatibility and fluorescence properties for bio-imaging, writable data storage, and anti-counterfeiting materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Michelle M. S. Lee, Eric Y. Y. Yu, Dingyuan Yan, Joe H. C. Chau, Qian Wu, Jacky W. Y. Lam, Dan Ding, Ryan T. K. Kwok, Dong Wang, Ben Zhong Tang
Summary: The aggregation-induced emission photosensitizer (AIEPS) has emerged as a promising option for bacterial theranostics. With the use of cationic AIEPS, it has been possible to discriminate and eliminate bacteria effectively. This study investigates the relationship between hydrophobicity variation of cationic amphiphilic AIEPS and bacterial targeting outcomes, providing insights into the design strategies for better development in bacterial theranostics.
Article
Materials Science, Multidisciplinary
Yi Qin, Xue Li, Shuai Lu, Miaomiao Kang, Zhijun Zhang, Yixiong Gui, Xiaopeng Li, Dong Wang, Ben Zhong Tang
Summary: We developed a general and straightforward protocol to formulate supramolecular cages with an aggregation-induced emission (AIE) tendency using donor-acceptor-donor (D-A-D) adducts as building blocks. A series of box-shaped cages MA-MG with adjustable fluorescence from red to the second near-infrared (NIR-II) region were successfully prepared. In particular, the emission maximum of MG was located at 981 nm, behaving like the rare NIR-II emissive supramolecular cages thus far, and the cage-loaded nanoparticles MGNPs featured a high absolute quantum yield in the NIR-II region, enabling them to perform well in blood vessel imaging.
ACS MATERIALS LETTERS
(2023)
Review
Chemistry, Multidisciplinary
Michelle M. S. Lee, Eric Y. Yu, Joe H. C. Chau, Jacky W. Y. Lam, Ryan T. K. Kwok, Dong Wang, Ben Zhong Tang
Summary: Fluorescence bioimaging is a sensitive, selective, and non-invasive method for visualizing biological processes on the microscale. However, conventional organic fluorophores have limitations in long-term monitoring and tracing of intracellular processes due to their poor photostability and low signal-to-noise ratio. On the contrary, AIE luminogens (AIEgens) possess photophysical properties that enable real-time and long-term intracellular dynamics visualization. This review summarizes the recent development of AIE probes for unveiling intracellular processes, providing inspiration and directions for the future design and development of AIEgens.
MATERIALS CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Physical
Xue Li, Hao Yang, Ping Zheng, Danmin Lin, Zhijun Zhang, Miaomiao Kang, Dong Wang, Ben Zhong Tang
Summary: This review comprehensively summarizes the major advancements of aggregation-induced emission luminogens (AIEgens) in energy transformation, including the conversion of solar, chemical, mechanical, and electrical energies, as well as representative applications relying on energy transformation. The challenges and future perspectives in this direction are also emphasized.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Review
Chemistry, Physical
Peiying Liu, Danxia Li, Miaomiao Kang, Yinzhen Pan, Ziyao Wen, Zhijun Zhang, Dong Wang, Ben Zhong Tang
Summary: The continuous threat of antibiotic-resistant bacterial biofilms due to the complex microenvironment has posed a challenge to public health. The exploration of high-performance antibiofilm systems fueled by the urgent demand for effective biofilm combating has drawn attention to aggregation-induced emission luminogens (AIEgens). This review summarizes the current progress of AIEgens in bacterial biofilm imaging and antibiofilm theranostics, highlighting their potential in fluorescence imaging, enzyme-responsive biofilm imaging, and eradication of preexisting biofilms.
