Review
Chemistry, Multidisciplinary
Yixin Zhang, Jiawei Tan, Yiyun Chen
Summary: Chemical labeling of proteins in live cells with aryl azides induced by visible-light irradiation has become a burgeoning field in chemical biology. Visible light irradiation activates aryl azides to generate highly reactive intermediates, enabling protein labeling for functionalization, crosslinking, and profiling. The activation mechanism of aryl azides by light irradiation is categorized as photolysis, energy-transfer, and electron-transfer. The applications of aryl azides in extracellular and intracellular protein labeling in live cells induced by visible light are discussed, including recent advances in red-light-induced extracellular protein labeling.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Chuan Wan, Yuena Wang, Chenshan Lian, Qi Chang, Yuhao An, Jiean Chen, Jinming Sun, Zhanfeng Hou, Dongyan Yang, Xiaochun Guo, Feng Yin, Rui Wang, Zigang Li
Summary: This study develops a novel visible-light-driven thioacetal activation reaction for facile modification of histidine residues. The method allows chemo-selective modification on peptides and proteins, enabling efficient histidine-proteome profiling. 78 histidine containing proteins were found for the first time, most of which function in metal accumulation in brain related diseases.
Article
Chemistry, Multidisciplinary
Rafael D. C. Gallo, Guilherme Cariello, Tales A. C. Goulart, Igor D. Jurberg
Summary: Considering the rapid advancement of synthetic technologies using visible light in the past 15 years, the use of photocatalysts has been justified. It has been observed that certain classes of organic molecules are capable of directly absorbing visible light. This includes diazo compounds, which can be photolytically activated by visible light, leading to free carbene intermediates and potential new reactivities. This article presents the contributions of various research groups in this area, providing an overview of the current state of the art.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Chao Pei, Claire Empel, Rene M. Koenigs
Summary: C-H functionalization is a rapidly advancing field in organic synthesis and is crucial for minimizing the ecological and economic impact. However, the ubiquity and low reactivity of C-H bonds present challenges, often requiring harsh conditions. Recent research has revealed a new approach, using a single transition-metal complex as both a photosensitizer and catalyst, to achieve C-H functionalization without an exogenous photosensitizer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Can Xu, Shang Gong, Xiang Wu, Yuwei Wu, Qiuyan Liao, Ying Xiong, Zhen Li, Hongding Tang
Summary: The development of carbazole-based photo-bleachable dyes as free radical initiators for visible light polymerization showed promising results in effectively initiating the photopolymerization of thick materials. Carbazole-based dyes like CM-2 and CI-2 demonstrated better free radical initiating efficiencies and successful polymerization of thick films under visible light irradiation. These findings suggest great potential for deep photocuring of thick materials using these dyes.
Article
Chemistry, Organic
Siyu Liang, Kaijie Wei, Yajun Lin, Tuming Liu, Dian Wei, Bing Han, Wei Yu
Summary: This paper describes two new visible-light-promoted radical reactions of alpha-azido amides. N-aryl alpha-azido tertiary amides were transformed into aminyl radicals through reduction of the azido group, followed by N-to-N aryl migration to form alpha-anilinyl-functionalized amides; on the other hand, alpha-azido secondary amides reacted with ethanol and i-Pr2NEt to yield imidazolinone products.
Article
Chemistry, Multidisciplinary
Qiang Liu, Yu Lu, He Sheng, Chao-Shen Zhang, Xiao-Di Su, Zhi-Xiang Wang, Xiang-Yu Chen
Summary: The sigma-hole effect is utilized to facilitate the photolysis of phosphonium iodide salts, selectively generating fluoromethyl radicals, allowing for mono-, di-, and trifluoromethylation reactions using fluoromethylphosphonium salts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Julie A. Peterson, Ding Yuan, Arthur H. Winter
Summary: By mixing different photoremovable protecting groups, independent optical control over a mixture of photocaged substrates can be achieved through wavelength-selective activation using long-wavelength light.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinrui Bai, Shijia Li, Dan Qi, Zhuoheng Song, Bin Li, Lin Guo, Lijuan Song, Wujiong Xia
Summary: In this article, a visible-light-induced trifluoromethylsulfonylation reaction of diazo compounds is reported. The developed synthetic method utilizes the coordination of relatively rare trifluoromethyl sulfone radicals to the Mn(acac)(3) catalyst, leading to the formation of alpha-trifluoromethyl sulfone esters in good to moderate yields (up to 82%). The reaction exhibits broad substrate scope and can be easily conducted under mild conditions. Furthermore, the plausible mechanism of the reaction was investigated through DFT calculations.
Article
Chemistry, Organic
Jinrui Bai, Shijia Li, Dan Qi, Zhuoheng Song, Bin Li, Lin Guo, Lijuan Song, Wujiong Xia
Summary: A visible-light-induced trifluoromethylsulfonylation reaction of diazo compounds is presented. The reaction captures relatively rare trifluoromethyl sulfone radicals through coordination to the Mn(acac)3 catalyst, resulting in the synthesis of alpha-trifluoromethyl sulfone esters in good to moderate yields (up to 82%). The protocol demonstrates broad substrate scope and can be conducted under mild reaction conditions. Additionally, a plausible reaction mechanism was investigated through DFT calculations.
Article
Chemistry, Physical
Maria P. S. Rodrigues, Andre H. B. Dourado, Antonio G. Sampaio de Oliveira-Filho, Ana P. de Lima Batista, Moritz Feil, Katharina Krischer, Susana Cordoba de Torresi
Summary: This paper describes the application of gold-rhodium core-shell nanoflowers (Au@Rh NFs) as a model system for the electrochemical CO2 reduction reaction. The nanoparticles consist of a gold nucleus surrounded by rhodium branches, combining Au localized surface plasmon resonance (LSPR) and Rh catalytic properties. The influence of LSPR excitation on the catalytic properties was evaluated for different excitation wavelengths and various Au@Rh NF metallic ratios. Our catalysts showed enhanced activity upon LSPR excitation, demonstrating that LSPR excitation may lead to improved performance even with a low content of metallic NFs (2% Au + Rh in Carbon Vulcan). Electrochemical impedance spectroscopy (EIS) experiments performed under LSPR excitation suggest that the superior activity under illumination is related to lower energetic barriers that facilitate the desorption of adsorbed species compared to dark conditions.
Article
Chemistry, Physical
Maria Paula de Souza Rodrigues, Andre H. B. Dourado, Leonardo de O. Cutolo, Luanna S. Parreira, Tiago Vinicius Alves, Thomas J. A. Slater, Sarah J. Haigh, Pedro H. C. Camargo, Susana Ines Cordoba de Torresi
Summary: The study presents a mechanism for enhancing the hydrogen evolution reaction (HER) performance using gold-rhodium core-shell nanoflowers (Au@Rh NFs), demonstrating how LSPR excitation from Au NPs can improve the catalytic properties of Rh. This offers insights into optimizing catalytic performance for future applications.
Article
Chemistry, Organic
Xiao-Hong Xu, Jing-Song Zhen, Xian Du, Han Yuan, Yi-Hui Li, Man-Hei Chu, Yong Luo
Summary: A visible-light-mediated late-stage sulfonylation of anilines with sulfonamides under simple reaction conditions is demonstrated. Various primary or secondary sulfonamides, including several pharmaceuticals, were successfully incorporated through N-S bond activation and C-H bond sulfonylation. The synthetic utility of this strategy is highlighted by the construction of complex anilines bearing diverse bioactive groups.
Article
Chemistry, Multidisciplinary
Claire Empel, Chao Pei, Rene M. Koenigs
Summary: This article provides a concise overview of photolysis reactions of diazoalkanes in photochemistry. It covers the discoveries in physical organic chemistry, examples of singlet carbene intermediates in organic synthesis, advances in cascade reactions and unusual protonation reactions under photochemical conditions. It also discusses the electronic control of singlet and triplet carbene intermediates and the recent advances in using weakly colored diazoalkanes in dye-sensitized reactions to access radical or triplet carbene intermediates.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hua Sheng, Hongna Zhang, Wenjing Song, Hongwei Ji, Wanhong Ma, Chuncheng Chen, Jincai Zhao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Yuchao Zhang, Shiqi Jiang, Wenjing Song, Peng Zhou, Hongwei Ji, Wanhong Ma, Weichang Hao, Chuncheng Chen, Jincai Zhao
ENERGY & ENVIRONMENTAL SCIENCE
(2015)
Article
Chemistry, Multidisciplinary
Hai-Ying Jiang, Peng Zhou, Yuanyuan Wang, Ran Duan, Chuncheng Chen, Wenjing Song, Jincai Zhao
ADVANCED MATERIALS
(2016)
Article
Chemistry, Physical
Yanhui Lv, Xiaofeng Cao, Haiying Jiang, Wenjing Song, Chuncheng Chen, Jincai Zhao
APPLIED CATALYSIS B-ENVIRONMENTAL
(2016)
Review
Biochemistry & Molecular Biology
Yuchao Zhang, Hongwei Ji, Wanhong Ma, Chuncheng Chen, Wenjing Song, Jincai Zhao
Article
Chemistry, Physical
Hongna Zhang, Peng Zhou, Zuofeng Chen, Wenjing Song, Hongwei Ji, Wanhong Ma, Chuncheng Chen, Jincai Zhao
JOURNAL OF PHYSICAL CHEMISTRY C
(2017)
Article
Chemistry, Multidisciplinary
Qian Zhu, Ran Duan, Hongwei Ji, Wenjing Song, Chuncheng Chen, Wanhong Ma, Jincai Zhao
RESEARCH ON CHEMICAL INTERMEDIATES
(2017)
Article
Chemistry, Physical
Yuanyuan Wang, Qian Zhu, Yan Wei, Yanjun Gong, Chuncheng Chen, Wenjing Song, Jincai Zhao
APPLIED CATALYSIS B-ENVIRONMENTAL
(2018)
Article
Chemistry, Physical
Anan Liu, Yuchao Zhang, Wanhong Ma, Wenjing Song, Chuncheng Chen, Jincai Zhao
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2018)
Article
Chemistry, Physical
M. Kyle Brennaman, Melissa K. Gish, Leila Alibabaei, Michael R. Norris, Robert A. Binstead, Animesh Nayak, Alexander M. Lapides, Wenjing Song, Robert J. Brown, Javier J. Concepcion, Joseph L. Templeton, John M. Papanikolas, Thomas J. Meyer
JOURNAL OF PHYSICAL CHEMISTRY C
(2018)
Article
Chemistry, Multidisciplinary
Yuchao Zhang, Hongna Zhang, Anan Liu, Chuncheng Chen, Wenjing Song, Jincai Zhao
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Multidisciplinary Sciences
Meng Li, Fengxia Bao, Yue Zhang, Wenjing Song, Chuncheng Chen, Jincai Zhao
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2018)
Article
Chemistry, Multidisciplinary
Wei Chang, Chunyan Sun, Xibin Pang, Hua Sheng, Yue Li, Hongwei Ji, Wenjing Song, Chuncheng Chen, Wanhong Ma, Jincai Zhao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Review
Chemistry, Physical
Yuanyuan Wang, Yan Wei, Wenjing Song, Chuncheng Chen, Jincai Zhao
Article
Chemistry, Physical
Qian Zhu, Yuanyuan Wang, Hongna Zhang, Ran Duan, Chuncheng Chen, Wenjing Song, Jincai Zhao
APPLIED CATALYSIS B-ENVIRONMENTAL
(2017)