• Title/Summary/Keyword: Spiro compounds

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Synthesis and Characterization of Highly Fluorescent and Thermally Stable π-Conjugates involving Spiro[fluorene-9,4'-[4H]indeno[1,2-b]furan]

  • Kowada, Toshiyuki;Ohe, Kouichi
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.577-581
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    • 2010
  • Spiro[fluorene-9,4'-[4H]indeno[1,2-b]furan] was synthesized, and its $\pi$-conjugation was efficiently elongated using palladium-catalyzed C-H arylation of a furan moiety. The resulting $\pi$-conjugated compounds showed intense fluorescence and extremely high thermal stability.

An Efficient Method for Multicomponent Synthesis of Spiro[4H-pyran-oxindole] Derivatives Catalyzed by Magnesium Perchlorate

  • Wu, Chunlei;Shen, Runpu;Chen, Jianhui;Hu, Chunqi
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2431-2435
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    • 2013
  • A simple and efficient method for the synthesis of spiro[4H-pyran-oxindole] derivatives by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds in the presence of catalytic amount of magnesium perchlorate in 50% aqueous ethanol medium has been described.

Blue OLEDs Utilizing Spiro[fluorene 7,9'-benzofluorene]-type Compounds as Hosts and Dopants

  • Kim, Joo-Han;Jeon, Young-Min;Jang, Ji-Geun;Ryu, Sang-Ouk;Chang, Ho-Jung;Lee, Chil-Won;Kim, Joon-Woo;Gong, Myoung-Seon
    • Bulletin of the Korean Chemical Society
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    • v.30 no.3
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    • pp.647-652
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    • 2009
  • A novel spiro-type host material, 5-[4-(1-naphthyl)phenyl]-spiro[fluorene-7,9'-benzofluorene] (BH-1PN) and three new dopants, namely, 5-[diphenylamino)phenyl]-spiro[fluorene-7,9'-benzofluorene] (BH-1TPA), 5-[4-(N-phenyl (m-tolyl)amino]-spiro[fluorene-7,9'-benzofluorene] (BH-1MDPA) and 5-[(N-phenyl)-2-naphthyl]amino-spiro[fluorene- 7,9'-benzofluorene] (BH-1NPA) were designed and successfully prepared using the Suzuki or amination reactions. The electroluminescence characteristics of BH-1PN as a blue host material doped with each of the blue dopants were evaluated. The structure of the device is ITO/DNTPD/NPB/BH-1PN:5% dopant/Alq3/Al-LiF. The device obtained from BH-1PN doped with diphenyl-[4-(2-[1,1;4,1]terphenyl-4-yl-vinyl)phenyl]-amine (BD-1) showed good color purity, efficiency, luminance, and current-density characteristics.

Synthesis and Antimicrobial Activity of some New 2-Indolinone Derived Oximes and Spiro-Isoxazolines

  • El Gendy, Adel A.;Ahmedy, Aly M.
    • Archives of Pharmacal Research
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    • v.23 no.4
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    • pp.310-314
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    • 2000
  • The synthesis and spectral analysis of some new 1,3-dihydro-3-hydroxy-3-[2-hydroxyimino-2-(substituted phenyl)ethyll-2H-indol-2-ones (21-32) and spiro[3H-indol-3,5'-(4'H)-isoxazol]-2(1 H)-ones (33-44) are described. Sixteen of the synthesized compounds were screened in vitro for their growth inhibitory activity against thirteen species of microorganisms, viz, S. aureus, S. epidermidis, S. faecalis, B. subtilis, B. cereus, E. aerogens, E. coli, P. aeruginosa, P. vulgaris, A. baumonia, A. faecalis, C. albicans and S. cervicae. Most of the compounds exhibited significant antimicrobial activity especially the oximes 28 and 29.

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Ab Initio Study of Mechanism of Forming Spiro-Ge-Heterocyclic Ring Compound From C2Ge=Ge: and Formaldehyde

  • Lu, Xiuhui;Li, Yongqing;Ming, Jingjing
    • Bulletin of the Korean Chemical Society
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    • v.34 no.12
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    • pp.3690-3694
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    • 2013
  • The $H_2Ge=Ge:$ and its derivatives ($X_2Ge=Ge:$, X = H, Me, F, Cl, Br, Ph, Ar${\ldots}{\ldots}$) is a new species. Its cycloaddition reactions is a new area for the study of germylene chemistry. The mechanism of the cycloaddition reaction between singlet state Cl2Ge=Ge: and formaldehyde has been investigated with CCSD(T)//MP2/$6-31G^*$ method. From the potential energy profile, it could be predicted that the reaction has only one dominant reaction pathway. The reaction rule presented is that the two reactants first form a fourmembered Ge-heterocyclic ring germylene through the [2+2] cycloaddition reaction. Because of the 4p unoccupied orbital of Ge: atom in the four-membered Ge-heterocyclic ring germylene and the ${\pi}$ orbital of formaldehyde forming a ${\pi}{\rightarrow}p$ donor-acceptor bond, the four-membered Ge-heterocyclic ring germylene further combines with formaldehyde to form an intermediate. Because the Ge: atom in intermediate hybridizes to an $sp^3$ hybrid orbital after transition state, then, intermediate isomerizes to a spiro-Ge-heterocyclic ring compound via a transition state. The research result indicates the laws of cycloaddition reaction between $H_2Ge=Ge:$ and formaldehyde, and laid the theory foundation of the cycloaddition reaction between $H_2Ge=Ge:$ and its derivatives ($X_2Ge=Ge:$, X = H, Me, F, Cl, Br, Ph, Ar${\ldots}{\ldots}$) and asymmetric ${\pi}$-bonded compounds, which is significant for the synthesis of small-ring and spiro-Ge-heterocyclic compounds. The study extends research area and enriches the research content of germylene chemistry.

Investigation of Photoluminescence Properties for Dibenzosiloles and Tetrabenzospirosilole

  • Jang, Seunghyun
    • Journal of Integrative Natural Science
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    • v.3 no.2
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    • pp.107-111
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    • 2010
  • Silicon-containing ${\pi}$-conjugated compounds, especially silacyclopentadienes (siloles), have emerged as a new class of electroactive materials with good electron transport properties in OLEDs. 9,9'-spiro-9-silabifluorene compound as well as its starting material 2,2'-dibromobiphenyl have been synthesized with higher yields. Spirosilabifluorene is expected to be an efficient host material for the blue-light emitting diodes. 9,9'-spiro-9-silabifluorene, 1,1-dichloro-1-silafluorene, and 1,1-dimethyl-1-silafluorene were characterized by $^1H$-NMR, UV/Vis and photoluminescence spectroscopy.

Synthesis and in vitro Activity of Novel 1β-Methylcarbapenems Having Spiro[2,4]heptane Moieties. Part II

  • Park, Hyeong-Beom;Jung, Myung-Ho;Cho, Jung-Hyuck;Oh, Chang-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.29 no.8
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    • pp.1472-1478
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    • 2008
  • The synthesis of a new series of 1$\beta$-methylcarbapenems having spiro[2,4]heptane moieties is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituents at the pyrrolidine ring was investigated. Most of the compounds were found to be more active compared to imipenem against Gram-negative bacteria. A particular compound (IIIc) having 7-oxo-5- azaspiro[2,4]heptane moiety showed the most potent antibacterial activity.

Preparation of Novel Fused Ring Spiro[benzotetraphene-fluorene] Derivatives and Application for Deep-Blue Host Materials

  • Kim, Min-Ji;Lee, Chil-Won;Gong, Myoung-Seon
    • Bulletin of the Korean Chemical Society
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    • v.35 no.6
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    • pp.1639-1646
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    • 2014
  • A series of novel fused-ring spiro compounds, spiro[benzo[ij]tetraphene-7,9'-fluorene] (SBTF) derivatives containing an end-capping aryl substituent at both the C3 and C10-positions hasbeen designed and synthesized via multi-step Suzuki coupling reactions. 3-(1-Naphthyl)-10-phenylSBTF (1N-PSBTF), 3-(2-naphthyl)-10-phenylSBTF (2N-PSBTF) and 3-[4-(1-naphthyl)phenyl]-10-phenylSBTF (NP-PSBTF) showed improved glass transition temperatures ($T_g$) with good thermal stability. Their photophysical, electrochemical, and electroluminescent properties were investigated and were used to construct blue organic light emission diodes (OLEDs). The typical OLED devices showed excellent performance; the NP-PSBTF-based device exhibited highly efficient deep blue-light emission with a maximum efficiency of 5.27 cd/A (EQE, 4.63%) with CIE (x = 0.133, y = 0.144). According to these characteristics, these deep-blue light emitting materials have sufficient potential for fluorescent OLED applications.

Synthesis of novel Heterocycles Through Reaction of Indolin-2-one Derivatives with Active Methylene and Amino Reagents

  • Abdel-Latif, F.F.;Ahmed, E.Kh.;Mekheimer, R.;Mashaly, M.M.
    • Archives of Pharmacal Research
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    • v.20 no.5
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    • pp.507-509
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    • 1997
  • Several new spiro compounds were synthesized via one-pot ternary condensation of isatin, malononitrile and each of thiobarbituric acid, barbituric, 3-methyl-pyrazolin-5-one, 1-phenyl-3-methyl-pyrazolin-5-one, acetylacetone, benzoylacetone, ethyl acetoacetate, phenacyl cyanide or ethyl-cyanoacetate dimer. Structures and reaction mechanisms were reported and supported via a second synthetic route.

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