35160-95-3Relevant academic research and scientific papers
Propargyl-allenyl isomerizations and electrocyclizations for the functionalization of phosphonium salts: One-pot synthesis of polysubstituted vinylbenzenes and naphthalenes
Zhao, Guoqing,Zhang, Qianyun,Zhou, Hongwei
, p. 3492 - 3496 (2013)
Phosphonium salts are widely used in organic synthesis as the precursor of Wittig reagents but highly functionalized phosphonium salts are not readily available. We have developed a sequence of propargyl-allenyl isomerizations and electrocyclizations for the functionalization of phosphonium salts via simple starting materials, which may provide an efficient one-pot synthesis of polysubstituted vinylbenzenes and naphthalenes. Copyright
Configurationally Stable Platinahelicene Enantiomers for Efficient Circularly Polarized Phosphorescent Organic Light-Emitting Diodes
Yan, Zhi-Ping,Luo, Xu-Feng,Liu, Wei-Qiang,Wu, Zheng-Guang,Liang, Xiao,Liao, Kang,Wang, Yi,Zheng, You-Xuan,Zhou, Liang,Zuo, Jing-Lin,Pan, Yi,Zhang, Hongjie
, p. 5672 - 5676 (2019)
Chiral materials with circularly polarized luminescence (CPL) are potentially applicable for 3D displays. In this study, by decorating the pyridinyl-helicene ligands with -CF3 and -F groups, the platinahelicene enantiomers featured superior configurational stability, as well as high sublimation yield (>90 %) and clear CPPL properties, with dissymmetry factors (|gPL|) of approximately 3.7×10?3 in solution and about 4.1×10?3 in doped film. The evaporated circularly polarized phosphorescent organic light-emitting diodes (CP-PhOLEDs) with two enantiomers as emitters exhibited symmetric CPEL signals with |gEL| of (1.1–1.6)×10?3 and decent device performances, achieving a maximum brightness of 11 590 cd m?2, a maximum external quantum efficiency up to 18.81 %, which are the highest values among the reported devices based on chiral phosphorescent PtII complexes. To suppress the effect of reverse CPEL signal from the cathode reflection, the further implementation of semitransparent aluminum/silver cathode successfully boosts up the |gEL| by over three times to 5.1×10?3.
Indole-Based Aza[n]helicenes (n=5, 6) with Violet-Blue Fluorescence and Two-Photon Absorption (TPA)
Hu, Zhenhao,Li, Li,Liu, Zhi,Liu, Zhiqiang,Zhang, Dingchao,Li, Kunlun
, p. 742 - 750 (2020)
A series of indole-based helicenes, namely, 15-hexyl-15H-tetraphenyl[1,2-e]indole (HTPI), 14-hexyl-14H-benzo[4’,5’]thieno [2’,3’:7,8]naphtha[1,2-e]indole (HBTNI), 7-hexyl-7H-indolo[5,4-k] phenanthridine (HIPD) and 3-hexyl-3H-phenanthro[4,3-e]indole (HPI)
Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
Frydrych, Ivo,Urban, Milan,?arek, Jan,Benická, Sandra,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan
, (2021/07/28)
A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.
Water Docking Bias in [4]Helicene
Domingos, Sérgio R.,Martin, Kévin,Avarvari, Narcis,Schnell, Melanie
supporting information, p. 11257 - 11261 (2019/07/12)
We report on the one- and two-water clusters of [4]helicene, the smallest polycyclic aromatic hydrocarbon with a helical sense, which were captured in the gas phase using high-resolution rotational spectroscopy. The structures of the complexes are unambiguously revealed using microwave spectra of isotopically enriched species. In the one-water cluster, the apparent splitting pattern is consistent with a tunneling motion that encompasses an exchange of strongly and weakly bonded water hydrogens. This motion is “locked” in the two-water cluster. The relevant intermolecular contacts, symmetry, and aromaticity effects are unveiled for the microsolvated chiral topologies. These observations entail the first glance at the structures and internal dynamics of the water binding motifs of a chiral polycyclic aromatic hydrocarbon.
12-hexyl-12H-phenanthrene [3, 4-f] indole compound and synthetic method and application thereof
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Paragraph 0066-0068, (2019/08/20)
The present invention relates to a 12-hexyl-12H-phenanthrene [3, 4-f] indole compound and a synthesis method and application thereof, and belongs to the technical field of organic synthesis. By the adoption of the 12-hexyl-12H-phenanthrene [3, 4-f] indole
Intermolecular interactions in molecular crystals and their effect on thermally activated delayed fluorescence of helicene-based emitters
Klimash, Anastasia,Pander, Piotr,Klooster, Wim T.,Coles, Simon J.,Data, Przemyslaw,Dias, Fernando B.,Skabara, Peter J.
supporting information, p. 10557 - 10568 (2018/10/24)
Here, we discuss the influence of the crystal structure on the photophysical properties of two new TADF emitters containing a non-planar helical moiety. The presence of solvent in the crystal lattice of a diaza[5]helicene-based compound alters molecular p
One on the basis of [...]high fused ring of [6] spiral alkene compound and its synthesis method
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Paragraph 0065; 0070, (2017/09/02)
The invention provides a kind of highly condensed ring [6]helicene compounds (I) based on fluorene and naphthalene and synthetic method thereof, and belongs to the technical field of chemical engineering. The highly condensed ring [6]helicene compounds with photoelectric functions are successfully prepared by taking naphthalene and fluorene derivatives as raw materials and employing a photocatalytic cyclization method. The synthetic method has the advantages of high yield, short time, simple operation and the like, also employs common cheap reagents, helps to reduce preparation cost, and is easy for popularization and application. The highly condensed ring [6]helicene compounds based on fluorene and naphthalene has extremely good solubility in different organic solvents, and are beneficial for purification and film making. Multiple highly condensed ring [6]helicene compounds can be obtained by introducing different substitutes. The highly condensed ring [6]helicene compounds based on fluorene and naphthalene is hopeful to be widely applied to fields such as organic electroluminescence, Organic field effect transistor, organic second-order nonlinear or chiral liquid crystal, biological medicines and the like.
Deep-blue electroluminescence from nondoped and doped organic light-emitting diodes (OLEDs) based on a new monoaza[6]helicene
Hua, Wanming,Liu, Zhi,Duan, Lian,Dong, Guifang,Qiu, Yong,Zhang, Baojie,Cui, Deliang,Tao, Xutang,Cheng, Na,Liu, Yongjun
, p. 75 - 84 (2015/02/19)
A new organic electroluminescent material, monoaza[6]helicene (1), was successfully prepared via an effective photochemical reaction in about 10 minutes with high productivity. The thermal, photophysical, electrochemical properties, quantum chemical and X-ray structural studies as well as characteristics of organic light-emitting diodes were fully investigated. 1 exhibited excellent solubility and high thermal stability. The first singlet excitation energy of 1 was measured to be around 2.92 eV with a HOMO level of -5.19 eV and a LUMO level of -2.27 eV. Helical molecular geometry of 1 effectively blocked the π-conjugation and decreased the close-packing of molecules. Both the nondoped and doped OLEDs emitted deep-blue light at 444 and 462 nm with CIE coordinates of (0.15, 0.09) and (0.15, 0.10). The doped OLED based on 1 was the first example of helicenes as light emitters that exhibited a brightness of more than 3000 cd m-2 with high color purity and excellent efficiency stability.
One-pot synthesis of gem-difluorostyrenes from benzyl bromide via olefination of phosphonium ylide with difluorocarbene
Deng, Xiao-Yun,Lin, Jin-Hong,Xiao, Ji-Chang
, p. 116 - 120 (2015/11/10)
A new approach for the synthesis of gem-difluorostyrenes from benzyl bromide is described. Quaternization of triphenylphosphine with benzyl bromide to give phosphonium salts, deprotonation of the corresponding phosphonium salts to produce phosphonium ylide, and the subsequent olefination of phosphonium ylide with difluorocarbene generated from difluoromethylene phosphobetaine (Ph3P+CF2CO2-) by decarboxylation can occur smoothly in one-pot, furnishing the final gem-difluorostyrenes in good yields.
