Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Ferrocenyl Chalcones with 1- and 2-Naphthalenyl Group: Spectroscopic Characterizations and Electrochemical Properties

  • Jeon, Hyokyung (Department of Chemistry, Seoul Women's University) ;
  • Lee, Ji-Won (Department of Chemistry, Seoul Women's University) ;
  • Song, Sung-Ye (Department of Chemistry, Seoul Women's University) ;
  • Noh, Dong-Youn (Department of Chemistry, Seoul Women's University)
  • Received : 2014.06.27
  • Accepted : 2014.08.07
  • Published : 2014.10.20
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Abstract

Keywords

EXPERIMENTAL

Electron ionization-mass spectrometry (EI-MS) measurement was performed at the National Center for Inter-University Research Facilities (NCIRF). Infrared spectra were recorded by the KBr pellet method using a Perkin Elmer Spectrum 100 spectrometer between 4,000−400 cm−1. 1H NMR measurements were performed at room temperature using an Avance 300 (Bruker) spectrometer using CDCl3 as the solvent. UV-Vis spectra were measured using an HP 8452A diode array spectrophotometer. Fluorescence spectra of 1Naph-Fc and 2Naph-Fc were recorded at room temperature in several solvents such as CHCl3, CH3CN, EtOH and MeOH using a Cary Eclipse fluorescence spectrophotometer (Varian). Electrochemical properties of Naph-Fc compounds were investigated by cyclic voltammetry at room temperature using a CHI 620A electrochemical analyzer (CHI Instrument Inc.) under the following conditions: 0.5 mM sample and 0.1 M n-Bu4N·BF4 electrolyte dissolved in 10 mL CH2Cl2, using round-disk (r = 0.2 cm) Pt working-electrode, Ag/AgCl reference electrode, and Pt-wire counter electrode (φ = 0.5 mm) at a scan rate of 100 mV s−1. All the redox potentials were measured against reference Fc/Fc+ redox couple (E1/2 = 0.554 V).

Preparation of 1Naph-Fc

An ethanol solution (40 mL) of ferrocenecarboxaldehyde (215 mg, 1 mmol), 1-acetonaph-thone (0.152 mL, 1 mmol), and NaOH (200 mg, 5 mmol) was stirred overnight at room temperature (Scheme 2). The red-colored reaction mixture was then dried under reduced pressure. The product was extracted with CH2Cl2 and dried with anhydrous MgSO4. After filtration, the solution was evaporated. The solid product was then purified by column chromatography (SiO2, CH2Cl2). EI-MS (m/z, %) 366 (M+, 100), 301(M+−Cp, 90); FTIR (KBr, cm−1): 3093, 2926 (Ar C−H), 1655, 1628 (C=C), 1580 (C=O), 1508, 1460 (Ar C=C), 1284, 1247, 1133, 1104, 1044 (Ar C−H ip def), 806, 780 (Ar C−H oop def), 484, 497 (Fe-ring vib); 1H NMR (300 MHz, ppm, CDCl3) δ 8.27 (1H, CH, d, J = 9.60 Hz), 7.97 (2H, CH, m), 7.70 (1H, CH, d, J = 6.90 Hz), 7.58 (3H, CH, m), 7.48 (1H, CO−CH=CH, d, J = 15.6 Hz), 6.89 (1H, CO−CH=CH, d, J = 15.6 Hz), 4.55 (2H, Cp, t, J = 1.80 Hz), 4.50 (2H, Cp, t, J = 1.80 Hz), 4.19 (5H, Cp, s).

Preparation of 2Naph-Fc

An ethanol solution (40 mL) of ferrocenecarboxaldehyde (215 mg, 1 mmol), 2-acetonaph-thone (170 mg, 1 mmol), and NaOH (200 mg, 5 mmol) was stirred overnight at room temperature (Scheme 2). The red-colored reaction mixture was then dried under reduced pressure. The product was extracted with CH2Cl2 and dried with MgSO4. After filtration, the solution was evaporated. The solid product was then purified by column chromato-graphy (SiO2, CHCl3:CH2Cl2 = 1:5). EI-MS (m/z, %) 366 (M+, 100), 301(M+ −Cp, 80); FTIR (KBr, cm−1) 3089, 3058, 2926 (Ar C−H), 1653, 1627 (C=C), 1586 (C=O), 1470 (Ar C=C), 1250, 1216, 1187, 1125, 1026 (Ar C−H ip def), 822, 757 (Ar C−H oop def), 497, 480 (Fe-ring vib); 1H NMR (300 MHz, ppm, CD2Cl2) δ 8.55 (1H, CH, s), 8.08 (2H, CH, m), 7.97 (2H, CH, m), 7.83 (1H, CO−CH=CH, d, J = 15.3 Hz), 7.64 (2H, CH, m), 7.36 (1H, CO−CH=CH, d, J = 15.3 Hz), 4.71 (2H, Cp, t, J = 1.80 Hz), 4.56 (2H, Cp, t, J = 1.80 Hz), 4.24 (5H, Cp, s).

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