• Title/Summary/Keyword: 2,2'-biimidazole

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Synthesis and Characterization of 2,2'-Biimidazole (2,2'-Biimidazole의 합성 및 구조분석)

  • Collier, Harvest L.;Cho, Il Young
    • Analytical Science and Technology
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    • v.11 no.1
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    • pp.8-12
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    • 1998
  • The 2,2'-Biimidazole was synthesized by the reaction between glycol and ammonium solution. The correct solid structure of 2,2'-biimidazole in this method reported either trans ($C_{2h}$) or cis ($C_{2v}$) form. In this study, the correct structure of 2,2'-biimidazole was analysed by both FTIR and Raman spectroscopy using mutual exclusion properties of them. Also, it was analysed by $^1H$ and $^{13}C$ NMR and computer molecular modeling. The structure of 2,2'-biimidazole found to be trans ($C_{2h}$) than cis ($C_{2v}$) by comparison between FTIR and Raman Spectra. This results agree with computer molecular modeling and x-ray crystallography. This study provide good evidence for identifying structural orientation of the 2,2'-biimidazole containing pyridyl nitrogen.

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Structural, Electrochemical, DNA Binding and Cleavage Properties of Nickel(II) Complex [Ni(H2biim)2(H2O)2]2+ of 2,2'-Biimidazole

  • Jayamani, Arumugam;Thamilarasan, Vijayan;Ganesan, Venketasan;Sengottuvelan, Nallathambi
    • Bulletin of the Korean Chemical Society
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    • v.34 no.12
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    • pp.3695-3702
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    • 2013
  • A nickel(II) complex $[Ni(H_2biim)_2(H_2O)_2](ClO_4)_2{\cdot}H_2O$ (1) of biimidazole ligand has been synthesized and characterized (Where $H_2biim$ = 2,2'-biimidazole). The single crystal X-ray diffraction of the complex shows a dimeric structure with six coordinated psudo-octahedral geometry. The cyclic voltammograms of complex exhibited one quasireversible reduction wave ($E_{pc}=-0.61V$) and an irreversible oxidation wave ($E_{pa}=1.28V$) in DMF solution. The interaction of the complex with Calf-Thymus DNA (CT-DNA) has been investigated by absorption and fluorescence spectroscopy. The complex is an avid DNA binder with a binding constant value of $1.03{\times}10^5M^{-1}$. The results suggest that the nickel(II) complex bind to CT-DNA via intercalative mode and can quench the fluorescence intensity of EB bind to CT-DNA with $K_{app}$ value of $3.2{\times}10^5M^{-1}$. The complex also shown efficient oxidative cleavage of supercoiled pBR322 DNA in the presence of hydrogen peroxide as oxidizing agent. The DNA cleavage by complex in presence of quenchers; viz. DMSO, KI, $NaN_3$ and EDTA reveals that hydroxyl radical or singlet oxygen mechanism is involved. The complex showed invitro antimicrobial activity against four bacteria and two fungi. The antimicrobial activity was nearer to that of standard drugs and greater than that of the free ligand.

Blue Emitting Cationic Iridium Complexes Containing Two Substituted 2-Phenylpyridine and One 2,2'-Biimidazole for Solution-Processed Organic Light-Emitting Diodes (OLEDs)

  • Yun, Seong-Jae;Seo, Hoe-Joo;Song, Myungkwan;Jin, Sung-Ho;Kim, Young Inn
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3645-3650
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    • 2012
  • Two new blue emitting cationic iridium(III) complexes with two substituted 2-phenlypyridine ligands as main ligands and one 2,2'-biimidazole as an ancillary ligand, $[(L1)_2Ir(biim)]Cl$ (1) and $[(L2)_2Ir(biim)]Cl$ (2), where L1 = 2-(2',4'-difluorophenyl)-4-methylpyridine, L2 = 2-(2',4'-difluoro-3'-trifluoromethylphenyl)-4-methylpyridine and biim = 2,2'-biimidazole, were synthesized for applications in phosphorescent organic light-emitting diodes (PhOLEDs). Their photophysical, electrochemical and electroluminescent (EL) device performances were examined. The photoluminescent (PL) spectra revealed blue phosphorescence in the 450 to 485 nm range with a quantum yield of more than 10%. The iridium(III) compounds studied showed good solubility in organic solvents with no solvatochromism dependent on the solvent polarity. The solution-processed OLEDs were prepared with the configuration, ITO/PEDOT:PSS (40 nm)/mCP:Ir(III) (70 nm)/OXD-7 (20 nm)/LiF (1 nm)/Al (100 nm), by spin coating the emitting layer containing the mCP host doped with the iridium phosphors. The best performance of the fabricated OLEDs based on compound 1 showed an external quantum efficiency of 4.5%, luminance efficiency of 8.52 cd $A^{-1}$ and blue emission with the CIE coordinates (x,y) of (0.16, 0.33).

Tuning Photophysical and Electrochemical Properties of Heteroleptic Cationic Iridium(III) Complexes Containing Substituted 2-Phenylquinoxaline and Biimidazole

  • Sengottuvelan, Nallathambi;Seo, Hoe-Joo;Kang, Sung-Kwon;Kim, Young-Inn
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2309-2314
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    • 2010
  • Design and syntheses of four red phosphorescent heteroleptic cationic iridium(III) complexes containing two substituted phenylquinoxaline (pqx) or benzo[b]thiophen-2-yl-pyridin (btp) main ligands and one 2,2'-biimidazole (H2biim) ancillary ligand are reported: [$(pqx)_2$Ir(biim)]Cl (1), [$(dmpqx)_2$Ir(biim)]Cl (2), [$(dfpqx)_2$Ir(biim)]Cl (3), [$(btp)_2$Ir(biim)]Cl (4). Complex 1 showed a distorted octahedral geometry around the iridium(III) metal ion with cis metallated carbons and trans nitrogen atoms. The absorption, emission and electrochemical properties were systematically evaluated. The complexes exhibited red phosphorescence in the spectral range of 580 to 620 nm with high quantum efficiencies of 0.58 - 0.78 in both solution and solid-state at room temperature depending on the cyclometalated main ligands. The cyclic voltammetry of the complexes (1-3) showed a metal-centered irreversible oxidation in the range of 1.40 to 1.90 V as well as two quasi reversible reduction waves from -1.15 to -1.45 V attributed to the sequential addition of two electrons to the more electron accepting heterocyclic portion of two distinctive cyclometalated main ligands, whereas complex 4 showed a reversible oxidation potential at 1.24 V and irreversible reduction waves at -1.80 V.