85111-44-0Relevant academic research and scientific papers
A time-resolved near-infrared phosphorescent iridium(iii) complex for fast and highly specific peroxynitrite detection and bioimaging applications
Li, Yuanyan,Wu, Yongquan,Chen, Luyan,Zeng, Hong,Chen, Xiaoyong,Lun, Weican,Fan, Xiaolin,Wong, Wai-Yeung
, p. 7612 - 7618 (2019)
Peroxynitrite (ONOO-), one of the reactive oxygen/nitrogen species (ROS/RNS) found in vivo, plays crucial roles in many physiological and pathological processes. The ability to selectively and sensitively determine ONOO-in vivo is im
Photo- and electroluminescence from deep-red- and near-infrared- phosphorescent tris-cyclometalated iridium(III) complexes bearing largely π-extended ligands
Ikawa, Shigeru,Yagi, Shigeyuki,Maeda, Takeshi,Nakazumi, Hiroyuki,Fujiwara, Hideki,Koseki, Shiro,Sakurai, Yoshiaki
, p. 14 - 19 (2013)
Deep-red- and near-infrared-phosphorescent tris-cyclometalated iridium(III) complexes bearing largely π-extended cyclometalated (C^N) ligands were newly synthesized, and their photo- and electroluminescence properties were investigated. When 2-(benzo[b]furan-2-yl)quinoline and 2-(benzo[b]thiophen-2-yl) quinoline were employed as C^N ligands, deep-red photoluminescence was obtained (Ir-1a and Ir-1b; λPL in CH2Cl2, 647 and 652 nm, respectively). In the case of the isoquinoline analogues of Ir-1a and Ir-1b, emission maxima were further red-shifted, ranging from deep-red to near-infrared regions (Ir-2a and Ir-2b; λPL in CH 2Cl2, 696 and 690 nm, respectively). Especially, Ir-2b showed an excellent photoluminescence quantum yield (ΦPL = 0.15), and a polymer light-emitting diode doped with Ir-2b exhibited deep-red-near-infrared electroluminescence with a high external quantum efficiency (λEL = 694 nm, ηext max = 1.41%).
Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls
Blakemore, David C.,Cervantes-Reyes, Alejandro,Chinigo, Gary M.,Smith, Aaron C.,Szostak, Michal
supporting information, p. 1678 - 1683 (2022/03/14)
Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.
Phenothiazine-containing iridium complex as well as preparation method and application thereof
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Paragraph 0072; 0076, (2021/08/21)
The invention provides a phenothiazine-containing iridium complex as well as a preparation method and application thereof, and belongs to the technical field of photosensitizers. On the basis that a central iridium atom of the metal iridium complex is a heavy atom, the long-life triplet excitation state of the metal iridium complex is regulated and controlled through phenothiazine, the emission spectrum of the designed iridium complex containing the phenothiazine structure is located in a near-infrared region, and the iridium complex belongs to near-infrared phosphorescence emission iridium complexes. The phenothiazine structure is introduced into the N^N ligand of the iridium complex, so that the capability of generating O2 by the iridium complex can be improved. The iridium complex provided by the invention can generate singlet oxygen in both a solution and tumor cells under the illumination condition of more than 470nm, has the capability of photodynamically killing cancer cells, and provides possibility for photodynamic therapy.
Dicyano-containing iridium complex as well as preparation method and application thereof
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Paragraph 0056-0058, (2021/09/04)
The invention provides a dicyano-containing iridium complex as well as a preparation method and application thereof, and belongs to the technical field of photosensitizers. According to the invention, based on the fact that the central iridium atom of the metal iridium complex is a heavy atom, a dicyano structure is introduced into an N^N ligand to regulate and control the triplet excited state with long service life of the metal iridium complex, which is beneficial to inducing generation of active oxygen species (such as singlet oxygen and hydroxyl radicals), and the ability of the metal iridium complex to generate active oxygen is increased; under the illumination condition, the iridium complex containing the dicyano group can generate singlet oxygen, hydroxyl free radicals and other active oxygen species in a solution and tumor cells, and has the capability of photodynamically killing tumor cells, so that the possibility is provided for constructing the iridium complex containing the dicyano group for photodynamic therapy.
Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
, p. 10747 - 10754 (2021/08/16)
This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
Modifications to the Aryl Group of dppf-Ligated Ni σ-Aryl Precatalysts: Impact on Speciation and Catalytic Activity in Suzuki-Miyaura Coupling Reactions
Mohadjer Beromi, Megan,Banerjee, Gourab,Brudvig, Gary W.,Charboneau, David J.,Hazari, Nilay,Lant, Hannah M. C.,Mercado, Brandon Q.
supporting information, p. 3943 - 3955 (2018/10/24)
There is currently significant interest in the development of efficient nickel precatalysts for cross-coupling. In this work, 14 nickel(II) precatalysts of the form (dppf)Ni(aryl)(X) (dppf = 1,1′-bis(diphenylphosphino)ferrocene, X = Cl, Br) were synthesiz
Substituents engineered deep-red to near-infrared phosphorescence from tris-heteroleptic iridium(iii) complexes for solution processable red-NIR organic light-emitting diodes
Kim, Hae Un,Sohn, Sunyoung,Choi, Wanuk,Kim, Minjun,Ryu, Seung Un,Park, Taiho,Jung, Sungjune,Bejoymohandas
, p. 10640 - 10658 (2018/10/24)
Research on near-infrared- (NIR-) emitting materials and devices has been propelled by fundamental and practical application demands surrounding information-secured devices and night-vision displays to phototherapy and civilian medical diagnostics. However, the development of stable, highly efficient, low-cost NIR-emitting luminophores is still a formidable challenge owing to the vulnerability of the small emissive bandgap toward several nonradiative decay pathways, including the overlapping of ground- and excited-state vibrational energies and high-frequency oscillators. Suitable structural designs are mandatory for producing an intense NIR emission. Herein, we developed a series of deep-red to NIR emissive iridium(iii) complexes (Ir1-Ir4) to explore the effects of electron-donating and electron-withdrawing substituents anchored on the quinoline moiety of (benzo[b]thiophen-2-yl)quinoline cyclometalating ligands. These substituents help engineer the emission bandgap systematically from the deep-red to the NIR region while altering the emission efficiencies drastically. Single-crystal X-ray structures authenticated the exact coordination geometry and intermolecular interactions in these new compounds. We also performed an in-depth and comparative photophysical study in the solution, neat powder, doped polymer film, and freeze matrix at 77 K states to investigate the effects of substitution on the excited-state properties. These studies were conducted in conjunction with density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations. Most importantly, the -CH3 substituted Ir1, unsubstituted Ir2, and -CF3 substituted complex (Ir4) were promising novel compounds with bright phosphorescence quantum efficiency in doped polymer films. Using these novel molecules, deep-red to NIR emissive organic light-emitting diodes (OLEDs) were fabricated using a solution-processable method. The unoptimized device exhibited maximum external quantum efficiency (EQE) values of 2.05% and 2.11% for Ir1 and Ir2, respectively.
A phosphorescence iridium complex synthesis and its used for cercarian fluorescence-labeled
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Paragraph 0065, (2018/01/11)
The invention belongs to the field of photobiology labeling for preventing and treating parasitic diseases, and relates to synthesis of a phosphorescent iridium complex and the purpose of the phosphorescent iridium complex for the fluorescence labeling of
Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles
Kojima, Masahiro,Kanai, Motomu
, p. 12224 - 12227 (2016/10/13)
Catalytic acceptorless dehydrogenation is an environmentally benign way to desaturate organic compounds. This process is traditionally accomplished with transition-metal-based catalysts. Herein, a borane-catalyzed, metal-free acceptorless dehydrogenation of saturated N-heterocycles is disclosed. Tris(pentafluorophenyl)borane was identified as a versatile catalyst, which afforded several synthetically important N-heteroarenes in up to quantitative yield. Specifically, the present metal-free catalytic system exhibited a uniquely high tolerance toward sulfur functionalities, and demonstrated superior reactivity in the synthesis of benzothiazoles compared to conventional metal-catalyzed systems. This protocol can thus be regarded as the first example of metal-free acceptorless dehydrogenation in synthetic organic chemistry.
