- A C4N4 Diaminopyrimidine Fluorophore
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A new scaffold for producing efficient organic fluorescent materials was identified: 2,5-diamino-4,6-diarylpyrimidine featuring a C4N4 elemental composition. Single-step installation of two aryl groups at the 4,6-positions of the pyrimidine core delivered
- Noda, Hidetoshi,Asada, Yasuko,Maruyama, Tatsuro,Takizawa, Naoki,Noda, Nobuo N.,Shibasaki, Masakatsu,Kumagai, Naoya
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- Highly luminescent dinuclear platinum(II) complexes incorporating bis-cyclometallating pyrazine-based ligands: A versatile approach to efficient red phosphors
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A series of luminescent dinuclear platinum(II) complexes incorporating diphenylpyrazine-based bridging ligands (LnH2) has been prepared. Both 2,5-diphenylpyrazine (L2H2) and 2,3-diphenylpyrazine (L3H2) are able to undergo cyclometalation of the two phenyl rings, with each metal ion binding to the two nitrogen atoms of the central heterocycle, giving, after treatment with the anion of dipivaloyl methane (dpm), complexes of formula {Pt(dpm)} 2Ln. These compounds are isomers of the analogous complex of 4,6-diphenylpyrimidine (L1H2). Related complexes of dibenzo(f,h)quinoxaline (L4H2), 2,3-diphenyl-quinoxaline (L5H2), and dibenzo[3,2-a:2′,3′-c]phenazine (L6H2) have also been prepared, allowing the effects of strapping together the phenyl rings (L4H2 and L 6H2) and/or extension of the conjugation from pyrazine to quinoxaline (L5H2 and L6H2) to be investigated. In all cases, the corresponding mononuclear complexes, Pt(dpm)LnH, have been isolated too. All 12 complexes are phosphorescent in solution at ambient temperature. Emission spectra of the dinuclear complexes are consistently red shifted compared to their mononuclear analogues, as are the lowest energy absorption bands. Electrochemical data and TD-DFT calculations suggest that this effect arises primarily from stabilization of the LUMO. Introduction of the second metal ion also has the effect of substantially increasing the molar absorptivity and, in most cases, the radiative rate constants. Meanwhile, extension of conjugation in the heterocycle of L5H2 and L6H2 and planarization of the aromatic system favored by interannular bond formation in L 4H2 and L6H2 leads to further red shifts of the absorption and emission spectra to wavelengths that are unusually long for cyclometalated platinum(II) complexes. The results may offer a versatile design strategy for tuning and optimizing the optical properties of d-block metal complexes for contemporary applications.
- Culham, Stacey,Lanoe, Pierre-Henri,Whittle, Victoria L.,Durrant, Marcus C.,Williams, J. A. Gareth,Kozhevnikov, Valery N.
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- Highly efficient orange phosphorescent organic light-emitting diodes based on an iridium(III) complex with diethyldithiocarbamate (S^S) as the ancillary ligand
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A novel iridium(iii) complex Ir(dpp)2(dta) (dppH = 4,6-diphenyl pyrimidine; dta = diethyldithiocarbamate) was synthesized and characterized. The complex displayed strong emissions at 575 nm with high photoluminescence quantum yields of 86% in the doped poly(methyl methacrylate) (PMMA) film at 1% doping concentration. The orange-yellow polymer light-emitting devices (PLEDs) based on Ir(dpp)2(dta) as a triplet emitter with different concentrations (x = 1%, 3%, 5%, 7% and 10%) doped in a polymeric host 70% poly(N-vinylcarbazole) (PVK) + 30% 2,2′-(1,3-phenylene)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole] (OXD-7) were fabricated with high luminance and efficiency. The device achieved an ideal turn-on voltage (-2) as well as electroluminescence efficiency (30.12 cd A-1) at 3% doping concentration.
- Mei, Qunbo,Chen, Chen,Tian, Ruqiang,Yang, Min,Tong, Bihai,Hua, Qingfang,Shi, Yujie,Fan, Quli,Ye, Shanghui
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- Iron-Catalyzed Alkyne-Based Multicomponent Synthesis of Pyrimidines under Air
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An iron-catalyzed sustainable, economically affordable, and eco-friendly synthetic protocol for the construction of various trisubstituted pyrimidines is described. A wide range of trisubstituted pyrimidines were prepared using a well-defined, easy to prepare, bench-stable, and phosphine-free iron catalyst featuring a redox-noninnocent tridentate arylazo pincer under comparatively mild aerobic conditions via dehydrogenative functionalization of alcohols with alkynes and amidines.
- Chakraborty, Gargi,Guin, Amit Kumar,Mondal, Rakesh,Paul, Nanda D.,Sarkar, Susmita
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p. 13186 - 13197
(2021/10/01)
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- Synthesis and biological evaluation of pyrimidine bridged combretastatin derivatives as potential anticancer agents and mechanistic studies
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A number of pyrimidine bridged combretastatin derivatives were designed, synthesized and evaluated for anticancer activities against breast cancer (MCF-7) and lung cancer (A549) cell lines using MTT assays. Most of the synthesized compounds displayed good
- Kumar, Bhupinder,Sharma, Praveen,Gupta, Vivek Prakash,Khullar, Madhu,Singh, Sandeep,Dogra, Nilambra,Kumar, Vinod
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p. 130 - 140
(2018/03/23)
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- Heterocyclic compound
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Provided is a novel heterocyclic compound which can be used for a light-emitting element, as a host material of a light-emitting layer in which a light-emittiing substance is dispersed. A heterocyclic compound represented by a general formula (G1) is prov
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Page/Page column 116; 117; 118
(2016/10/07)
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- Composite material, light-emitting element, light-emitting device, electronic device, and lighting device
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A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite mat
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Page/Page column 95-96
(2016/08/10)
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- High-brightness solution-processed phosphorescent OLEDs with pyrimidine-based iridium(iii) complexes
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Two heteroleptic cyclometalated iridium(iii) complexes, Ir(ppm)2(pic) and Ir(ppm)2(taz), using 4,6-diphenyl pyrimidine (Hppm) as a cyclometalating ligand, were successfully synthesized and characterized. Strong emission at 555 and 532 nm with high photoluminescence quantum yields of 83% and 86% in PMMA at 298 k were obtained for Ir(ppm)2(pic) and Ir(ppm)2(taz), respectively. Solution-processed organic light-emitting diodes (OLEDs) based on Ir(ppm)2(pic) and Ir(ppm)2(taz) showed high-brightness of 112 233 and 125 072 cd m-2, peak current efficiencies of 30.6 and 40.4 cd A-1 and maximum external quantum efficiencies of 10.4 and 17.3%, respectively, accompanied by very low efficiency roll-off values. The ancillary ligand taz tuned the emission to saturated green, and more importantly, it can significantly increase the spectral stability and device efficiency.
- Tong, Bi-Hai,Mei, Qun-Bo,Tian, Ru-Qiang,Yang, Min,Hua, Qing-Fang,Shi, Yu-Jie,Ye, Shang-Hui
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p. 34970 - 34976
(2016/05/19)
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- Light-emitting element
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A light-emitting element having high external quantum efficiency is provided. A light-emitting element having low drive voltage is provided. Provided is a light-emitting element which includes a light-emitting layer containing a phosphorescent compound, a first organic compound, and a second organic compound between a pair of electrodes. A combination of the first organic compound and the second organic compound forms an exciplex (excited complex). An emission spectrum of the exciplex overlaps with an absorption band located on the longest wavelength side of an absorption spectrum of the phosphorescent compound. A peak wavelength of the emission spectrum of the exciplex is longer than or equal to a peak wavelength of the absorption band located on the longest wavelength side of the absorption spectrum of the phosphorescent compound.
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- Composite material, light-emitting element, light-emitting device, electronic device, and lighting device
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A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite mat
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(2014/01/17)
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- HETEROCYCLIC COMPOUND, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE
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Provided is a novel heterocyclic compound which can be used in a light-emitting layer of a light-emitting element as a host material in which a light-emitting substance is dispersed. A heterocyclic compound represented by a general formula (G1) is provide
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Paragraph 0395
(2013/03/26)
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- HETEROCYCLIC COMPOUND, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, LIGHTING DEVICE, AND ORGANIC COMPOUND
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Provided is a novel heterocyclic compound which can be used in a light-emitting layer of a light-emitting element as a host material in which a light-emitting material is dispersed, i.e., a heterocyclic compound represented by a general formula (G1). Any one of R1 to R10 represents a substituent represented by a general formula (G1-1); another one of R1 to R10 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituent represented by a general formula (G1-2); and the others separately represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
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Paragraph 0459
(2013/04/10)
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- HETEROCYCLIC COMPOUND
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Provided is a novel heterocyclic compound which can be used for a light-emitting element, as a host material of a light-emitting layer in which a light-emitting substance is dispersed. A heterocyclic compound represented by a general formula (G1) is provided. In the formula, A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group, R11 to R19 separately represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.
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- Biphenyl-based diaminophosphine oxides as air-stable preligands for the nickel-catalyzed kumada-tamao-corriu coupling of deactivated aryl chlorides, fluorides, and tosylates
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A cooperative couple: Cooperative bimetallic activation of C-F and C-O bonds gave rise to easy coupling with aryl fluorides and tosylates. Novel air- and moisture-stable diaminophosphine oxides derived from 1,1′-biphenyl-2, 2′-diamine proved to be versatile preligands for the nickel-catalyzed cross-coupling of aryl Grignard reagents with a variety of deactivated aryl chlorides, fluorides, and tosylates (see scheme). Copyright
- Jin, Zhong,Li, Yan-Jing,Ma, Yong-Qiang,Qiu, Ling-Ling,Fang, Jian-Xin
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supporting information; experimental part
p. 446 - 450
(2012/02/15)
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- Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device and Lighting Device
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Provided is a novel substance that can emit phosphorescence. Alternatively, provided is a novel substance with high emission efficiency. An organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal is provided. Specifically, an organometallic complex having a structure represented by a general formula (G1) is provided. In the general formula (G1), R1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
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- ORGANOMETALLIC COMPLEX, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE AND LIGHTING DEVICE
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Provided is a novel substance that can emit phosphorescence. Alternatively, provided is a novel substance with high emission efficiency. An organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal is provided. Specifically, an organometallic complex having a structure represented by a general formula (G1) is provided. In the general formula (G1), R1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
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(2012/05/05)
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- Light-Emitting Device, Electronic Device, and Lighting Device Utilizing Phosphorescence
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A new light-emitting device utilizing phosphorescence is provided. Further, an electronic device and a lighting device which utilize phosphorescence are provided. One embodiment of the present invention is a light-emitting device including a phosphorescen
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(2012/11/08)
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- A method for the reductive scission of heterocyclic thioethers
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A mild, chemoselective, and generally high-yielding method for the reductive scission of heterocyclic thioethers is described. Suitable heterocycles have a thioether substituent at the 2-position relative to a ring heteroatom. The convenient and straightforward method is demonstrated with reactants which are not compatible with the standard Raney nickel conditions such as sulfides, sulfones, and thiophenes. In addition, benzyl esters, benzyl amides, and benzyl carbamates are tolerated by the reductive reaction conditions.
- Graham, Thomas H.,Liu, Wensheng,Shen, Dong-Ming
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supporting information; experimental part
p. 6232 - 6235
(2012/01/03)
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- A direct oxidative route for the synthesis of pyrimidines using heteropolyacids
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Pyrimidines are synthesized via a direct oxidative one-pot, three-component, reaction between 1,3-diketone, benzaldehydes, and ammonium acetate in the presence of catalytic amounts of Keggin-type heteropolyacids under refluxing conditions in good yields.
- Heravi, Majid M.,Sadjadi, Samaheh,Oskooie, Hossein A.,Shoar, Rahim Hekmat,Bamoharram, Fatemeh F.
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scheme or table
p. 662 - 666
(2011/03/21)
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- Aryl-aryl bonds formation in pyridine and diazine series. Diazines part 41
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The synthesis of several symmetrical polyaromatic compounds with pyridine or diazine units has been achieved by homocoupling of aryl halides with Pd(OAc)2 as catalyst. Cross-coupling reactions of aryl Grignard reagents with Fe(acac)3 as catalyst allowed the synthesis of various unsymmetrical polyaryl- or polyheteroaryl compounds with π-deficient rings.
- Boully, Ludovic,Darabantu, Mircea,Turck, Alain,Ple, Nelly
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p. 1423 - 1428
(2007/10/03)
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- Synthesis of 4,6-disubstituted pyrimidines via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine
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A series of 4,6-disubstituted pyrimidines were synthesized via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine.
- Qing, Feng-ling,Wang, Ruowen,Li, Benhan,Zheng, Xing,Meng, Wei-Dong
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- Arylation of halogenated pyrimidines via a suzuki coupling reaction
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The Suzuki coupling reaction has been used extensively for the synthesis of a wide variety of unsymmetrical biaryl compounds. We have extended this reaction to demonstrate the utility of preparing monophenyl-, diphenyl-, or triphenylpyrimidine depending on the reaction conditions. Further, it has been shown that chloropyrimidine substrates are preferable over iodo-, bromo-, or fluoropyrimidines.
- Schomaker,Delia
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p. 7125 - 7128
(2007/10/03)
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- Heterocyclopolyaromatics, IX: 4,4''',6,6'''-Tetraazahexa-m-phenylene and 4,4',4''',4'''',6,6',6''',6''''-Octaazahexa-m-phenylene
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The synthesis of the title compounds 4 and 9 is described.In contrast to hexa-m-phenylene (6) 4,4''',6,6'''-tetrazahexa-m-phenylene (4) is planar.This is explained by less Pitzer strain in the outer sphere of 4.From 4 a tetranitro derivative (7c) was obta
- Muke, Bernd,Kauffmann, Thomas
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p. 2739 - 2748
(2007/10/02)
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