636-41-9Relevant articles and documents
Symmetry-breaking intramolecular charge transfer in the excited state of meso-linked BODIPY dyads
Whited, Matthew T.,Patel, Niral M.,Roberts, Sean T.,Allen, Kathryn,Djurovich, Peter I.,Bradforth, Stephen E.,Thompson, Mark E.
, p. 284 - 286 (2012)
We report the synthesis and characterization of symmetric BODIPY dyads where the chromophores are attached at the meso position, using either a phenylene bridge or direct linkage. Both molecules undergo symmetry-breaking intramolecular charge transfer in the excited state, and the directly linked dyad serves as a visible-light-absorbing analogue of 9,9′-bianthryl.
Mechanisms of the Au- and Pt-catalyzed intramolecular acetylenic schmidt reactions: A DFT study
Xia, Yuanzhi,Huang, Genping
, p. 7842 - 7854 (2010)
The reaction mechanisms of the PtCl4- and Au(I)-catalyzed intramolecular acetylenic Schmidt reactions were analyzed by means of hybrid density functional calculations at the B3LYP/6-31G*(LANL2DZ) level of theory for better understanding of the
Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols
Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Manna, Kuntal
supporting information, p. 9029 - 9039 (2021/06/28)
Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.
Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction
Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae
supporting information, p. 23743 - 23749 (2021/10/14)
Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.
Thermal Behavior Analysis of Two Synthesized Flavor Precursors of N-alkylpyrrole Derivatives
Ai, Lvye,Liu, Mengzhen,Ji, Xiaoming,Lai, Miao,Zhao, Mingqin,Ren, Tianbao
, p. 2389 - 2397 (2019/08/01)
To expand the library of pyrrole-containing flavor precursors, two new flavor precursors—methyl N-benzyl-2-methyl-5-formylpyrrole-3-carboxylate (NBMF) and methyl N-butyl-2-methyl-5-formylpyrrole-3-carboxylate (NUMF)—were synthesized by cyclization, oxidation, and alkylation reactions. Thermogravimetry (TG), differential scanning calorimeter, and pyrolysis–gas chromatography/mass spectrometry were utilized to analyze the thermal degradation behavior and thermal degradation products of NBMF and NUMF. The TG-DTG curve indicated that the maximum mass loss rates of NBMF and NUMF appear at 310 and 268°C, respectively. The largest peaks of NBMF and NUMF showed by the differential scanning calorimeter curve were 315 and 274°C, respectively. Pyrolysis–gas chromatography/mass spectrometry detected small molecule fragrance compounds appeared during thermal degradation, such as 2-methylpyrrole, 1-methylpyrrole-2-carboxylic acid methyl ester, limonene, and methyl formate. Finally, the thermal degradation mechanism of NBMF and NUMF was discussed, which provided a theoretical basis for their application in tobacco flavoring additives.
Synthesis, electrochemical/photophysical properties and computational investigation of 3,5-dialkyl BODIPY fluorophores
Derin, Yavuz,Y?lmaz, Ra?it Fikret,Baydilek, ?brahim Halil,Atalay, Vildan Eniso?lu,?zdemir, Abdil,Tutar, Ahmet
, p. 130 - 135 (2018/06/14)
A series of 3,5 dimethyl and diethyl BODIPY with different substitutions at meso position are synthesized and characterized. Photophysical and electrochemical features of the 3,5 dialkyl BODIPY fluorophores are investigated using experimental and computational approaches. All fluorophores display absorption maxima around at 510 nm and emission maxima around at 520 nm which correspound to very narrow Stokes shift. Among the fluorophores, 3,5,8 alkylated BODIPYs are found to have high fluorescence quantum yield (1.00–0.93). 4-Bromophenyl group at meso position decreases fluorescence quantum yield of the dye while it increases with 4-methoxyphenyl group at meso position. The HOMO-LUMO energies of synthesized fluorophore compounds were calculated by B3LYP/6-31G(d,p) and B3LYP/6-311+G(d,p) levels in chloroform phase. Electron donating and accepting groups show increasing and decreasing effect on the band gaps of the fluorophores respectively.
BACKGROUND-FREE FLUORESCENT PROBES FOR LIVE CELL IMAGING
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Page/Page column 25, (2017/06/24)
BODIPY (boron-dipyrromethene) containing fluorescent compounds for use in live cell intracellular imaging are described. Methods of producing the compounds, methods of labeling tagged organelles, and methods of live cell intracellular imaging using the compounds/probes are described herein.
A General Copper Catalyst for Photoredox Transformations of Organic Halides
Michelet, Bastien,Deldaele, Christopher,Kajouj, Sofia,Moucheron, Cécile,Evano, Gwilherm
supporting information, p. 3576 - 3579 (2017/07/17)
A broadly applicable copper catalyst for photoredox transformations of organic halides is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl halides were shown to be smoothly activated through a rare Cu(I)/Cu(I)?/Cu(0) catalytic cycle. This complex efficiently catalyzes a series of radical processes, including reductions, cyclizations, and direct arylation of arenes.
Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules
Palao, Eduardo,Slanina, Tomá?,Muchová, Lucie,?olomek, Tomá?,Vítek, Libor,Klán, Petr
, p. 126 - 133 (2016/01/25)
Carbon monoxide-releasing molecules (CORMs) are chemical agents used to administer CO as an endogenous, biologically active molecule. A precise spatial and temporal control over the CO release is the major requirement for their applications. Here, we report the synthesis and properties of a new generation of transition-metal-free carbon monoxide-releasing molecules based on BODIPY chromophores (COR-BDPs) activatable by visible-to-NIR (up to 730 nm) light. We demonstrate their performance for both in vitro and in vivo experimental settings, and we propose the mechanism of the CO release based on steady-state and transient spectroscopy experiments and quantum chemical calculations.
Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane
Trofimov, Boris A.,Mikhaleva, Al'Bina I.,Ivanov, Andrei V.,Shcherbakova, Viktoria S.,Ushakov, Igor A.
, p. 124 - 128 (2015/02/02)
2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2-4 h), the yields of pyrroles ranging 11-85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions.
