- Nickel-Catalyzed N, N-Diarylation of 8-Aminoquinoline with Large Steric Aryl Bromides and Fluorescence of Products
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A simple and efficient methodology for the synthesis of large sterically hindered triarylamines in a single step was developed. A direct N,N-diarylation of 8-aminoquinoline with sterically hindered bromides, making use of inexpensive nickel as a catalyst and simple sodium salt as a base, gives the products in good to excellent yields. Various bromides and substituted 8-aminoquinolines are tolerated. Preliminary fluorescence results indicate that these sterically hindered and conjugated triarylamines may have some potential in material chemistry.
- Yan, Mingpan,Zhu, Longzhi,Zhang, Xingxing,Yin, Shuang-Feng,Kambe, Nobuaki,Qiu, Renhua
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p. 2514 - 2520
(2021/04/13)
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- Nickel-Catalyzed Remote C4-H Arylation of 8-Aminoquinolines
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A useful and convenient method for C-H bond arylation of 8-aminoquinoline motifs on the remote C4 position was developed. This method shows good functional group tolerance toward various Grignard reagents and aminoquinoline via a nickel catalysis, giving
- Zhu, Longzhi,Sheng, Xinghao,Li, You,Lu, Dong,Qiu, Renhua,Kambe, Nobuaki
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p. 6785 - 6789
(2019/09/07)
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- 2,9-dichloro-4,7-diphenyl-1,10 phenanthroline
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The invention relates to 2,9-dichloro-4,7-diphenyl-1,10 phenanthroline, which belongs to the technical field of synthesis of organic chemistry. A method comprises the steps of: firstly mixing and stirring 8-nitroquinoline with sulfuric acid, dropwise adding benzene while stirring, mixing SnCl2.2H2O with acetic acid, and then adding into the reaction mixture, after stirring and mixing, inflating nitrogen gas, stirring, rising temperature, performing heat preservation, cooling to room temperature, dropwise adding sodium hydroxide under stirring, mixing with the acetic acid, adding potassium permanganate, stirring at constant temperature, adding benzoyl chloride, then slowly pouring the reaction mixture into icy water, introducing chlorine after stirring, sealing for reaction, and adding the sodium hydroxide, filtering, extracting filtrate and filtrate slag with hot benzene, combining the extract liquor, adding anhydrous sodium sulfate for drying, rotating to evaporate the benzene, and performing suction filtration. The invention has the beneficial effects of simple synthetic conditions, no secondary pollution, less side productions and a yield of more than 86%.
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Paragraph 0005; 0009
(2016/10/10)
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- A new robust and highly sensitive FRET donor-acceptor pair: Synthesis, characterization, and application in a thrombin assay
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The synthesis of a new, robust fluorescence-resonance-energy-transfer (FRET) system is described. Its donor chromophore is derived from an N-allyl-substituted quinolinone attached to 4-bromophenyl-alanine via Heck cross-coupling. The resulting Fmoc-protected derivative 11 was used as building block in solid-phase peptide synthesis (SPPS). As FRET acceptor, a sulfonylated ruthenium(II)-bathophenanthroline complex with a peripheral COOH function was prepared for covalent attachment to target molecules. The UV/VIS absorption and emission spectra of peptides bearing only the donor (D) or acceptor (A) dye showed a good overlap of the emission band of the donor with the absorption band of the acceptor. The fluorescence spectra of a peptide bearing both dyes revealed an additional emission after excitation of the donor, which is due to indirect excitation of the acceptor via FRET. The long fluorescence lifetime of the RuII complex (0.53 μs) makes it well-suited for time-resolved measurements. As a first application of this new FRET system, the peptide 18, with the recognition sequence for the protease thrombin, flanked by the two dyes, was synthesized and successfully cleaved by the enzyme. The change in the ratio of the fluorescence intensities could be determined.
- Kainmueller, Eva K.,Bannwarth, Willi
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p. 3056 - 3070
(2008/01/27)
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- Divalent osmium complexes: Synthesis, characterization, strong red phosphorescence, and electrophosphorescence
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We report new divalent osmium complexes that feature strong red metal-to-ligand-charge-transfer (MLCT) phosphorescence and electrophosphorescence. The general formula of the complexes is Os(II)(N-N)2L-L, where N-N is either a bipyridine or a phenanthroline and L-L is either a phosphine or an arsine. New polypyridyl ligands synthesized are 4,4′-di(biphenyl)-2,2′-bipyridine (15) and 4,4′-di(diphenyl ether)-2,2′-bipyridine (16), and the 1,10-phenanthroline derivatives synthesized are 4,7-bis(p-methoxyphen-yl)-1,10-phenanthroline (17), 4,7-bis(p-bromophenyl)-1,10-phenanthroline (18), 4,7-bis(4′-phenoxybiphen-4-yl)-1,10-phenanthroline (19), and 4,7-bis(4-naphth-2-ylphenyl)-1,10-phenanthroline (20). 4,4′-Diphenyl-2,2′-bipyridine (21) and 4,7-diphenyl-1,10-phenanthroline (22) were also used in these studies. Strong π-acid ligands used were 1,2-bis(diphenylarseno) ethane (23), cis- 1,2-bis(diphenylphosphino)ethylene (24), and cis-1,2-vinylenebis(diphenylarsine) (25). Ligand 25 is used for the first time in these types of luminescent osmium complexes. These compounds feature strong MLCT absorption bands in the visible region and strong red phosphorescent emission ranging from 611 to 651 nm, with quantum efficiency up to 45% in ethanol solution at room temperature. Red organic light-emitting diodes (OLEDs) were successfully fabricated by doping the Os(II) complexes into blend of poly(N-vinylcarbazole) (PVK) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD). Brightness over 1400 cd/m2 for a double-layer device has been reached, with a turn-on voltage of 8 V. The maximum external quantum efficiency was 0.64%. Commission Internationale de I'Eclairage (CIE) chromaticity coordinates (x, y) of the red electrophosphorescence from the complexes are (0.65, 0.34), which indicates pure red emission.
- Carlson, Brenden,Phelan, Gregory D.,Kaminsky, Werner,Dalton, Larry,Jiang, Xuezhong,Liu, Sen,Jen, Alex K.-Y.
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p. 14162 - 14172
(2007/10/03)
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