119-75-5Relevant academic research and scientific papers
A new series of N-substituted tetraphenylethene-based benzimidazoles: Aggregation-induced emission, fast-reversible mechanochromism and blue electroluminescence
Zhang, Tengfei,Zhang, Ran,Zhao, Yun,Ni, Zhonghai
, p. 276 - 285 (2018)
Four new N-substituted tetraphenylethene-based benzimidazoles N-R-2-(4-(1,2,2-triphenylvinyl)phenyl)-1H-benzo[d]imidazoles (R = phenyl (3a), R = 4-(tert-butyl)phenyl (3b), R = n-butyl (3c), R = n-hexyl (3d)) were synthesized conveniently by cyclization reaction of 4-tetraphenylenthenealdehyde with N-substituted ortho-nitroaniline. The four compounds exhibit typical aggregation-induced emission (AIE) property with relatively high solid state absolute fluorescence quantum yields (38.1–65.7%) and fast-recoverable mechanochromism property with solid-state fluorescence change between blue and yellow-green. They are thermally stable with decomposition temperatures above 319 °C. Both of multilayer electroluminescence devices fabricated with compounds 3b and 3c as emitters are blue emission. The turn-on voltage of device based on compound 3b is 3.3 V with maximum luminance and current efficiency of 2470 cd/m2 and 1.48 cd/A, respectively.
11-(Tetrahydro-3 and 4-pyridinyl)dibenzo[b,e][1,4]diazepines undergo novel rearrangements on treatment with concentrated HBr
Cairns, James,Clarkson, Thomas R.,Hamersma, Johan A.M.,Rae, Duncan R.
, p. 1583 - 1585 (2002)
11-(1,2,5,6-Tetrahydro-1-methyl-3-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine on heating in conc. HBr afforded trans-5-(2-aminophenyl)-1,3,4,4a,5,10a-hexahydro-2-methylbenzo[b][1,6] naphthyridin-10(2H)-one in one step. The isomer 11-(1,2,5,6-tetrahydro-1-methyl-4-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine underwent a novel rearrangement resulting in the pentacycle, 4-amino-5,13-diaza-13-methyl-bicyclo[3.3.1]nonan[6,7,8-k,l]acridine.
Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2- phosphonate as the new ligand
Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
, p. 8107 - 8109 (2005)
We have developed a general, efficient, and inexpensive catalyst system for arylation of amines by using 10 mol % of CuI as the copper source, 20 mol % of diphenyl pyrrolidine-2-phosphonate (DPP) as the ligand, K3PO 4 as the base, and DMF containing 2% water (v/v) as the solvent.
Solution-processed efficient deep-blue fluorescent organic light-emitting diodes based on novel 9,10-diphenyl-anthracene derivatives
Zhang, Zhaohang,Jiang, Wei,Ban, Xinxin,Yang, Min,Ye, Shanghui,Huang, Bin,Sun, Yueming
, p. 29708 - 29717 (2015)
A series of 9,10-diphenyl-anthracene derivatives bearing either benzimidazole or carbazole moieties as substituents were synthesized and characterized as blue emitters for organic light-emitting diodes (OLEDs). Their optical, electrochemical and thermal properties have been investigated, and their molecular structure-property relationships were evaluated. These compounds both exhibited a high glass-transition temperature (Tg ≥ 195 °C) and a high decomposition temperature (Td ≥ 494 °C). The solution processed non-doped device using CAC as a fluorescence emitter showed a maximum luminance efficiency of 1.63 cd A-1, a maximum power efficiency of 0.77 lm W-1 and a maximum external quantum efficiency of 1.53%. By introducing 1,3-bis[4-tert-butylphenyl-1,3,4-oxadiazolyl] phenylene (OXD-7):polyvinylcarbazole (PVK) as host in the emitting layer, the doped deep-blue emitting device of CAC exhibited a turn-on voltage of 4.75 V, a maximum luminance efficiency of 3.03 cd A-1, a maximum power efficiency of 1.64 lm W-1 and a maximum external quantum efficiency of 2.81%. Our results demonstrate a promising approach to well-designed materials for use in deep-blue fluorescence OLED applications. This journal is
Synthesis, photophysics, and reverse saturable absorption of bipyridyl platinum(II) bis(acetylide) complexes bearing aromatic electron-withdrawing substituents on the acetylide ligands
Liu, Xu-Guang,Sun, Wenfang
, p. 10318 - 10325 (2014)
Three platinum(II) bipyridyl bis((7-R-fluoren-2-yl)acetylide) complexes (R = benzoyl (Pt-1), 2-(N-phenylbenzimidazoly) (Pt-2), or 2-(3-phenylquinoxalinyl) (Pt-3)) are synthesized and characterized. Their photophysical properties and reverse saturable absorption are systematically investigated via UV-vis absorption, emission, transient absorption, and nonlinear transmission spectroscopy/technique. All three complexes possess ligand-centered 1π,π transitions below 400 nm, and a broad, featureless 1MLCT/1LLCT absorption band in the region of 400-550 nm in CH2Cl2 solutions. They are emissive in a variety of fluid solutions at room temperature and at 77 K glassy matrix. On the basis of the emission lifetime, solvatochromic effect, and thermally induced Stokes shift, the emitting states are tentatively ascribed to 3π,π/3MLCT/3LLCT states for Pt-1, and predominantly 3MLCT/3LLCT states for Pt-2 and Pt-3 in polar solvents like CH3CN. Pt-1-Pt-3 also exhibit broad triplet excited-state absorption, i.e., 425-800 nm for Pt-1 and Pt-3, and 425-725 nm for Pt-2, from the same excited states that emit. Strong reverse saturable absorption (RSA) occurs at 532 nm for ns laser pulses from all of the complexes due to the stronger triplet excited-state absorption at this wavelength, suggesting that the π-conjugated aromatic electron-withdrawing substituents at the fluorenylacetylide ligands enhance the RSA of the Pt(II) diimine bis(acetylide) complexes.
A Simple and Efficient Flow Preparation of Pyocyanin a Virulence Factor of Pseudomonas aeruginosa
Mortzfeld, Frederik B.,Pietruszka, J?rg,Baxendale, Ian R.
, p. 5424 - 5433 (2019)
The synthesis of the naturally occurring toxin pyocyanin has been realized in a short 4 step sequence. The key photochemical reaction and isolation of the final product have been facilitated by the use of flow chemistry techniques and immobilised reagents. Using these procedures gram quantities of pyocyanin were easily prepared in high yield and purity.
N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis
Perin,Hok,Be?,Persoons,Vanstreels,Daelemans,Vianello,Hranjec
, (2021)
We present the design, synthesis and biological activity of novel N-substituted benzimidazole based acrylonitriles as potential tubulin polymerization inhibitors. Their synthesis was achieved using classical linear organic and microwave assisted techniques, starting from aromatic aldehydes and N-substituted-2-cyanomethylbenzimidazoles. All newly prepared compounds were tested for their antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2–0.6 μM), while being significantly less toxic than reference systems docetaxel and staurosporine, thus promoting them as lead compounds. Mechanism of action studies demonstrated that two most active compounds inhibited tubulin polymerization. Computational analysis confirmed the suitability of the employed benzimidazole-acrylonitrile skeleton for the binding within the colchicine binding site in tubulin, thus rationalizing the observed antitumor activities, and demonstrated that E-isomers are active substances. It also provided structural determinants affecting both the binding position and the matching affinities, identifying the attached NMe2 group as the most dominant in promoting the binding, which allows ligands to optimize favourable cation???π and hydrogen bonding interactions with Lys352.
Design, synthesis, and structure-activity relationships of novel imidazo[4,5-c]pyridine derivatives as potent non-nucleoside inhibitors of hepatitis C virus NS5B
Liu, Moyi,Xu, Qiaoling,Guo, Su,Zuo, Ruixi,Hong, Yue,Luo, Yong,Li, Yingxiu,Gong, Ping,Liu, Yajing
, p. 2621 - 2631 (2018)
The hepatitis C virus (HCV) NS5B polymerase is an attractive target for the development of novel and selective inhibitors of HCV replication. In this paper, the design, synthesis, and preliminary SAR studies of novel inhibitors of HCV NS5B polymerase based on the structure of tegobuvir have been described. The efforts to optimize the antiviral potency and reduce the treatment side effects with respect to genotype 1b resulted in the discovery of compound 3, which exhibited an EC50 of 1.163 nM and a CC50 >200 nM in a cell-based HCV replicon system assay. Additionally, testing for inhibition of the hERG channel showed a marked improvement over tegobuvir and the pharmacokinetic properties of compound 3 indicated that it was worthy of further investigation as a non-nucleoside inhibitor of HCV NS5B polymerase.
Schiff bases-titanium (III) & (IV) complex compounds: Novel photocatalysts in Buchwald-Hartwig C–N cross-coupling reaction
Absalan, Yahya,Ghandi, Khashayar,Gholizadeh, Mostafa,Kovalchukova, Olga,Mahmoudi, Ghodrat,Sarvestani, Hossein Sabet,Shad, Nazanin Noroozi,Strashnov, Pavel
, (2021/05/21)
Nine novel Schiff bases were derived from salicylic aldehyde and oxalic aldehyde, isolated, and their molecular and spatial structure were explored by a set of experiments (IR, CNMR, HNMR, CHN, SEM, XRD) and theoretical simulation (DFT def2-TZVP). A high potential was predicted in metal cations chelating. The isolated organic species were applied as the ligands in the reaction of complex formation with titanium (III) chloride and (IV) bromide and 12 novel complexes were synthesized and studied experimentally and theoretically. Using the UV–vis spectroscopic titration, the solution stability of the complexes was indicated. Depending on the nature of the Schiff base ligand, their formation constants were calculated in the range of 6.84–17.32. Using the DFT def2-TZVP theoretical method together with the experimental spectroscopic data, the coordination types of the ligands were investigated, and the structure of the complexes was proposed. The photocatalytic ability of the isolated complexes was tested in the C-N cross-coupling reaction under sunlight. Complexes exhibited high visible-light photocatalytic activity for a wide range of aromatic and benzylic amines including electron-withdrawing and electron-donating groups from moderate to good yields ranging in 50–85 %. The use of an inexpensive, clean, and renewable energy source (visible light) is the superiority of the developed photocatalytic systems.
A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines
Shi, Ji-cheng,Zhang, Lixue,Zhou, Fabin
, p. 238 - 243 (2021/09/07)
A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro groups. With the TXPhos-supported catalyst system, many partner combinations have been unprecedentedly realized and the base scope has been even extended to KOAc, which is even the best choice in the amination of 2-nitrochlorobenzene.
