Article
Chemistry, Multidisciplinary
Da-Liang Zhu, Shan Jiang, David James Young, Qi Wu, Hai-Yan Li, Hong-Xi Li
Summary: In this study, a catalyst-free visible-light-driven C(sp(2))-H arylation of unprotected phenols with arylbromides was developed to obtain 2-arylated phenols. This reaction occurs through the excitation of an electron donor-acceptor complex between a phenolate and an arylbromide, electron transfer, and debrominative C(sp(2))-C(sp(2)) coupling.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xiao-Di Su, Bei-Bei Zhang, Qiang Liu, Jin-Tang Cheng, Zhi-Xiang Wang, Xiang-Yu Chen
Summary: Enamides are useful precursors for the synthesis of bioactive compounds. A simple alternative method for their alkylation has been proposed in this study, which involves using visible light to irradiate a mixture of N-hydroxyphthalimide esters and enamides without the need for additives. The reaction is based on the photoactivation of a pi-pi stacking EDA complex between the substrates.
Article
Chemistry, Multidisciplinary
Chen Li, Bin Chen, Xiaodong Ma, Xueling Mo, Guozhu Zhang
Summary: A catalytic asymmetric alkylation of azoles with secondary 1-arylalkyl bromides through direct C-H functionalization was reported. The reaction, under blue-light photoexcitation, showed good reactivity and high stereoselectivity, providing an efficient strategy for the construction of chiral alkyl azoles at low temperature. The reactions are compatible with a wide range of azoles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Tanumoy Mandal, Sanju Das, Rohan Maji, Suman De Sarkar
Summary: An EDA-triggered HAT process has been developed for the efficient synthesis of alpha-alkoxy radicals from cyclic ethers, leading to the exclusive formation of exocyclic alkenylated ethers with E-selectivity. The judicious choice of a donor-acceptor pair as the HAT reagent, along with visible light irradiation, eliminates the need for photocatalysts or peroxides. Mechanistic studies reveal a radical reaction pathway under oxidative conditions.
Article
Chemistry, Multidisciplinary
Long-Yong Xie, Sha Peng, Li-Hua Yang, Cun Peng, Ying-Wu Lin, Xianyong Yu, Zhong Cao, Yu-Yu Peng, Wei-Min He
Summary: Aryl radicals were successfully generated from affordable aryl acyl peroxides in eco-friendly ethyl acetate under visible-light illumination without the need for any additive, metal catalyst, or external photosensitizer. The arylation of quinoxalin-2(1H)-ones was chemoselective and regioselective, allowing for good access to various 3-arylquinoxalin-2(1H)-ones.
Article
Chemistry, Organic
Yushi Tan, Wu Xuekun, Ya-Ping Han, Yuecheng Zhang, Hong-Yu Zhang, Jiquan Zhao
Summary: An efficient and convenient method for synthesizing 6-oxyalkylated 1,2,4-triazine-3,5(2H, 4H)-diones has been developed using a visible-light-induced cross-dehydrogenative coupling reaction. This reaction allows for a wide range of functional groups and uses a cheap and low-toxic photocatalyst and air as an oxidant. Additionally, the reaction can be driven by sunlight as a clean energy resource and has demonstrated utility in gram-scale reactions and the synthesis of key intermediates for bioactive molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Cui-Lian Zeng, Hao Wang, Di Gao, Zhen Zhang, Dong Ji, Wei He, Cheng-Kou Liu, Zhao Yang, Zheng Fang, Kai Guo
Summary: This study presents a green and gentle Minisci-type reaction method, in which the cross-dehydrogenative coupling of heteroarenes with aliphatic C(sp(3))-H bonds is achieved under visible-light irradiation. This method does not require oxidants or transition metal catalysts, and only the catalytic equivalent of CF3SO2Na and room temperature are needed to ensure an efficient reaction.
Article
Chemistry, Organic
Jaspreet Kaur, Ahmed Shahin, Joshua P. Barham
Summary: The study introduces a photocatalyst-free and mild visible light photochemical procedure for C(sp(3))-H arylation of amides. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant, leading to selective C(sp(3))-H arylation of the amide with the most electron-rich arene substrate. Mechanistic studies confirm the reaction takes place in a solvent cage holding components in close proximity.
Article
Chemistry, Organic
Ze-Yu Tian, Cheng-Pan Zhang
Summary: This study reported an efficient visible-light-induced cross-coupling reaction of arylsulfonium triflate with [Me4N][SeCF3] for the synthesis of various aryl trifluoromethyl selenoethers. The reaction exhibits operational simplicity, high efficiency, catalyst- and additive-free conditions, wide substrate scope, and good yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Rajesh T. T. Bhawale, Umesh A. A. Kshirsagar
Summary: A metal-catalyst-free, organic dye-catalyzed C3-H arylation of pyrido[1,2-a]pyrimidin-4-ones using visible light irradiation was developed. This simple and direct C-H functionalization approach effectively produced biologically significant C3 arylated pyrido[1,2-a]pyrimidin-4-one and thiazolo[3,2-a]pyrimidin-5-one derivatives, including medicinally important endothelial cell dysfunction inhibitor and anti-inflammatory agents with good functional group tolerance. The photoinduced direct C3-H arylation approach is suitable for scale-up synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Bholanath Maity, Sayan Dutta, Luigi Cavallo
Summary: C-sp3-C cross-coupling, a dream reaction in the chemical community, can be achieved by activating C-sp3-H bonds through visible light-induced transition metal-catalysis under mild reaction conditions. However, this research area is still in its early stages due to the chemical and technical complexity of this catalysis. Complementary experimental and theoretical mechanistic studies are essential for rational advances, as each approach alone is inadequate to clarify the operative mechanisms. In this tutorial review, we summarize representative experimental and computational mechanistic studies, highlighting the weaknesses, strengths, and synergies between the two approaches.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Yu Liu, Jia-Li Sui, Wen-Qin Yu, Bi-Quan Xiong, Ke-Wen Tang, Long-Jin Zhong
Summary: An efficient strategy for the visible-light-promoted decarboxylative alkylation of vinylcyclopropanes with alkyl N-(acyloxy)phthalimide esters has been developed using triphenylphosphine and lithium iodide as the photoredox system. This method involves the cleavage of dual C-C bonds and a single N-O bond and leads to the synthesis of 2-alkylated 3,4-dihydronaphthalenes. Additionally, when using Na-2-EosinY as the photocatalyst, the vinyl transfer products are obtained when vinylcyclobutanes or vinylcyclopentanes are utilized as alkyl radical receptors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qiao-Lin Wang, Zhaozhao Sun, Huawen Huang, Guojiang Mao, Guo-Jun Deng
Summary: A visible-light/nickel dual catalyzed stoichiometric coupling of methylarenes via bromine radical-enhanced HAT has been developed, demonstrating high synthetic utility in late-stage arylation or benzylation of drug-like and complex molecules.
Article
Chemistry, Physical
Chao Liu, Hui Liu, Xuan Zheng, Shanyi Chen, Qihong Lai, Changlong Zheng, Mingqiang Huang, Kaicong Cai, Zhixiong Cai, Shunyou Cai
Summary: A practical and efficient method for the direct oxidation of allylic C-H bonds has been established using visible-light-enabled photoredox agents. This metal-free protocol utilizes oxygen as the sole oxidant to produce functionalized enones at room temperature. When combined with acid-promoted dehydration, it enables the production of meta-functionalized phenols from simple cyclohexenols.
Article
Chemistry, Multidisciplinary
Lisa-Marie Altmann, Viviane Zantop, Pia Wenisch, Nina Diesendorf, Markus R. Heinrich
Summary: Metal and catalyst-free carbohydroxylations and carboetherifications have been achieved at room temperature through the combination of high aryl diazonium concentration and visible light irradiation. The weak charge transfer interactions between diazonium salt and alkene significantly influence the reaction course, offering potential for aryldiazonium-based radical arylations without the need for a photocatalyst or particular additive.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Limnology
Xu Yan, Min Cao, Qiang Fu, Ning Yang, Ningning Wang, Lin Song, Chao Li
Summary: In this study, lncRNAs in the intestine of black rockfish after Edwardsiella tarda infection were identified and analyzed. Results showed that these lncRNAs were significantly regulated and involved in metabolic and immune-related pathways. Co-expression of lncRNAs and mRNAs with metabolic and immunity functions were also found. This research provides a foundation for further investigation of the regulatory roles of lncRNAs in the intestinal immune response of black rockfish.
JOURNAL OF OCEANOLOGY AND LIMNOLOGY
(2023)
Correction
Chemistry, Applied
Luo Yang, Camille A. A. Correia, Chao-Jun Li
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Tao Wang, Abhishek Kumar Gupta, Sen Wu, Alexandra M. Z. Slawin, Eli Zysman-Colman
Summary: We discovered a general design principle for materials that exhibit multiple room-temperature phosphorescence (RTP) processes. By modulating the hybridization between donor and acceptor groups, we achieved multiple RTP processes in sp3 C-linked donor-acceptor compounds. However, in sp2 C-linked counterparts, only one locally excited triplet state phosphorescence was observed due to enhanced excitonic coupling. Our findings provide insights into the dynamics of higher-lying triplet excited states and offer a fundamental design principle for compounds with multiple RTP.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Materials Science, Biomaterials
Juan Ye, Yaling Qi, Jiao Chen, Shihu Zhang, Boyuan Liu, Yinjuan Zhao, Xianwen Yuan, Qi Cheng, Yang Yang, Furong Zhang, Hongliang Gao, Haoran Wang, Jing Wu, Feng Zhu, Chaojun Li, Peng Cao, Bin Xue
Summary: Currently, there are no approved pharmacotherapies for non-alcoholic fatty liver disease (NAFLD) in clinical practice. Despite evidence suggesting that geranylgeranyl diphosphate synthase (GGPPS) could be a potential therapeutic target for NAFLD, research on corresponding drug screening is limited. In this study, a GGPPS-targeted inhibitor, 4-AZ, was identified using a structure-based virtual small molecule screening method. The inhibitory effect of 4-AZ on GGPPS was confirmed through various assays, and its ability to attenuate hepatic steatosis and improve liver injury in mice was demonstrated. These findings highlight the potential of GGPPS inhibition as a novel strategy for the treatment of NAFLD.
Article
Nanoscience & Nanotechnology
Pagidi Sudhakar, Suman Kuila, Kleitos Stavrou, Andrew Danos, Alexandra M. Z. Slawin, Andrew Monkman, Eli Zysman-Colman
Summary: Extensive research has been conducted to develop thermally activated delayed fluorescence (TADF) emitters with pure-blue emission. In this study, a novel weak donor, 1,4-azaborine (AZB), was synthesized and combined with a triazine acceptor to create high-performance TADF emitters. The results showed that the AZB-Ph-TRZ emitter had a photoluminescence quantum yield (phi(PL)) of 27% and emitted at 415 nm, while the shortened analogue AZB-TRZ exhibited red-shifted emission and fast reverse intersystem crossing. These findings expand the toolkit for designing blue TADF materials in the future.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Subeesh Madayanad Suresh, Le Zhang, Tomas Matulaitis, David Hall, Changfeng Si, Gaetano Ricci, Alexandra M. Z. Slawin, Stuart Warriner, David Beljonne, Yoann Olivier, Ifor D. W. Samuel, Eli Zysman-Colman
Summary: Two multiresonant thermally activated delayed fluorescence (MR-TADF) emitters are demonstrated. The borylation of a deep-blue MR-TADF emitter, DIDOBNA-N, results in a new near-UV MR-TADF emitter, MesB-DIDOBNA-N, with a blueshifted and narrowed emission. DIDOBNA-N emits bright blue light with high efficiency, while the OLED based on MesB-DIDOBNA-N shows the highest efficiency and the bluest emission among MR-TADF OLEDs reported to date.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Ruofei Cheng, Chao-Jun Li
Summary: A novel method for the formation of Csp(3)-P-III bonds via the nickel-catalyzed cross-coupling of Umpolung carbonyls and phosphine chlorides is reported, resulting in alkylphosphines characterized as sulfides or borane-phosphine complexes with moderate to good yields. Valuable free alkylphosphines can be obtained by desulfurization or deboration of the products. The article also discusses a possible mechanistic pathway and represents the first example of using renewable carbonyls as latent organometallic reagents for cross-coupling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Cell Biology
Yiping Liu, Xuefeng Ge, Chao Li, Ting Xue
Summary: A continuous intestine cell line named SMI was established from turbot using tissue explant technique and had undergone more than 60 subcultures. The SMI cell line had a diploid chromosome number of 44 and showed characteristics of epidermal cells. It could be used as an ideal platform to explore gene function in vitro and exhibited immune functions similar to the intestinal epithelium in vivo.
IN VITRO CELLULAR & DEVELOPMENTAL BIOLOGY-ANIMAL
(2023)
Article
Biochemistry & Molecular Biology
Chengbin Gao, Xin Cai, Le Ma, Ting Xue, Chao Li
Summary: In this study, the TNF alpha was characterized and its roles in the immune system of black rockfish during bacterial infections were explored. The results showed that Ss_TNF alpha was significantly up-regulated in the spleen and intestine after infections, while down-regulated in PBLs. The expression patterns of other inflammatory cytokines were also observed.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Materials Science, Multidisciplinary
Tao Wang, Abhishek Kumar Gupta, David B. Cordes, Alexandra M. Z. Slawin, Eli Zysman-Colman
Summary: This study reports the observation of emission directly from the T-2 state in multi-resonant thermally activated delayed fluorescence (MR-TADF) emitters for the first time by modulating the conjugation between the emissive center and donor substituent. Theoretical and photophysical investigations reveal that the Delta E-S1T2 difference influences the reverse intersystem crossing rate. Therefore, designing MR-TADF emitters with degenerate S-1 and T-2 states provides a possible solution to mitigate device efficiency roll-off.
ADVANCED OPTICAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Shi Tang, John Marques dos Santos, Joan Rafols-Ribe, Jia Wang, Eli Zysman-Colman, Ludvig Edman
Summary: In this study, narrowband and efficient electroluminescence from multi-resonance thermally activated delayed fluorescence (MR-TADF) organic semiconductors in light-emitting electrochemical cells (LECs) is achieved by carefully selecting materials and developing the devices. The aggregation tendency of the MR-TADF emitter is inhibited by dispersing it into a compatible blend host and an ionic-liquid electrolyte. The designed metal-free active MR-TADF material exhibits a high external quantum efficiency of 3.8% with a narrow emission profile.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Changfeng Si, Tao Wang, Abhishek Kumar Gupta, David B. Cordes, Alexandra M. Z. Slawin, Jay S. Siegel, Eli Zysman-Colman
Summary: Corannulene-derived materials have been extensively studied in energy storage and solar cells. However, their potential as emitters in light-emitting sensors and OLEDs has been largely unexplored. In this study, a family of multi-D-A motifs, TCzPhCor, TDMACPhCor, and TPXZPhCor, were developed by using corannulene as the acceptor and different donors. These materials exhibit multiple phosphorescence and show promise in temperature sensing and OLED applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Materials Science, Multidisciplinary
Xinrui Chen, Sergey Bagnich, Robert Pollice, Bing Li, Yuanyuan Zhu, Rishabh Saxena, Yixiao Yin, Weiguo Zhu, Alan Aspuru-Guzik, Eli Zysman-Colman, Anna Koehler, Yafei Wang
Summary: This study prepares compounds with emissive TSCT and/or TBCT states and discovers the phenomenon of inverted energy gap. Intense emission and high photoluminescence quantum yields are measured in PMMA films. Compound DPS-m-bAc shows the fastest reverse intersystem crossing rate constant in a PMMA film, and the solution-processed device achieves the maximum external quantum efficiency.
ADVANCED OPTICAL MATERIALS
(2023)
Article
Chemistry, Organic
Megan Amy Bryden, Marco Villa, Andrea Fermi, Paola Ceroni, Eli Zysman-Colman
Summary: In this study, the performance of a newly developed photocatalyst, pDTCz-DPmS, was evaluated in a previously documented reaction. The results showed that the catalyst significantly increased the product yield, particularly in the presence of Hantzsch ester (HE). UV-Vis absorption and quenching studies revealed the photosensitization mechanisms of the catalyst.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Green & Sustainable Science & Technology
Chao Li, Kexin Yi, Shaogang Hu, Wulin Yang
Summary: A novel microbial separator was developed for air-breathing microbial fuel cells to protect cathodic catalytic activity. This concept effectively prevents biofouling, improves the stability of the cells, enhances chemical oxygen demand removal efficiency, prolongs lifespan, and reduces economic costs.
ENVIRONMENTAL SCIENCE AND ECOTECHNOLOGY
(2023)
