Ft ir 4100

Optical rotations and IR spectra were measured on a JASCO P-1020 polarimeter and a JASCO FT/IR-4100 (JASCO Corporation, Tokyo, Japan) spectrophotometer, respectively. HRESIMS spectra were measured on a Bruker APEX II mass spectrometer (Bruker, Bremen, Germany). ¹H and ¹³C NMR spectra were obtained on a Varian Unity INOVA 600 FT-NMR (or Varian Unity INOVA500 FT-NMR) instruments (Varian Inc., Palo Alto, CA, USA) at 600 MHz (or 500 MHz) for ¹H, and 150 MHz (or 125 MHz) for ¹³C in CDCl₃. Thin-layer chromatography (TLC) analyses were performed on precoated silica (Si) gel plates (Kieselgel 60 F-254, 0.2 mm), and Si gel (230–400 mesh) (Merck, Darmstadt, Germany) and C18-reversed phase Si gel (RP-18; 40–63 µM) (Parc-Technologique BLVD, Quebec, Canada) were used for column chromatography. Further purification and the isolation of compounds were performed by reversed-phase high-performance liquid chromatography (RP-HPLC) on a Hitachi L-2455 HPLC apparatus with a Supelco C18 column (250 × 21.2 mm, 5 μm).

The FT-IR (Fourier transform infrared spectrometer) spectrum was characterized by a Fourier transform infrared spectrometer (JASCO FT-IR 4100, JASCO Inc., Easton, MD, USA). X-ray photoelectron spectroscopy (XPS) spectra were obtained on a Thermo Scientific, Waltham, MA, USA Kα XPS spectrometer with a monochromatized, microfocused Al Kα line source. The crystal structure of all studied samples was obtained with the Rigaku D/max Ultima III instrument with Cu Kα radiation (λ = 0.154056 Å) (Rigaku, TX, USA). Raman spectroscopy was conducted on an Aberration-corrected Czerny–Turner monochromator (NRS-5100, JASCO Inc., Easton MD, USA) at 532.13 nm. The surface morphologies of the synthesized materials were studied by field-emission scanning electron microscopy (FE-SEM, HITACHI, SU-70, Fukuoka, Japan) and high-resolution transmission electron microscopy (HR-TEM, TECNAI F20 UT, FEI CO., Hillsboro, OR, USA). Energy-dispersive spectroscopy (EDS) elemental mapping was performed on a field-emission scanning electron microscopy (FE-SEM, HITACHI, EDX-200, Fukuoka, Japan). Nitrogen adsorption and desorption isotherms were determined by nitrogen physisorption at 77 K on a Micromeritics ASAP 2020 analyzer (Norcross, GA, USA). The samples were degassed at 150 °C for 12 h under vacuum before analysis.

Unless otherwise stated, all operations were performed in a MBraun UNIlab glovebox an argon atmosphere, in a Miwa 1ADB-3KTG glovebox under a nitrogen atmosphere, or by using high-vacuum and standard Schlenk techniques under an argon atmosphere. Benzene (anhydrous) was purchased from Kanto Chemical (Tokyo, Japan) and distilled from benzophenone ketyl prior to use. Other chemicals were purchased from commercial sources and used as received. ¹H-NMR spectra were recorded on a JEOL ECX-500, a JEOL ECX-400, or a JEOL ECS-400 spectrometer (JEOL, Tokyo, Japan), and the chemical shifts of ¹H are referenced to the residual proton signal of CDCl₃ (δ 7.25). ¹³C-NMR spectra were recorded on a JEOL ECX-500 or a JEOL ECX-400 spectrometer (JEOL, Tokyo, Japan), and the chemical shifts of ¹³C are referenced to the signal of CDCl₃ (δ 77.0). All spectra were assigned with the aid of DEPT (distorsionless enhancement by polarization transfer), COSY (correlated spectroscopy), HMQC (heteronuclear multi quantum correlation), and HMBC (heteronuclear multiple bond correlation) NMR experiments. IR spectra were recorded on a JASCO FT/IR-4100 (JASCO, Tokyo, Japan) by utilizing a JASCO ATR Pro550S unit. Melting points were measured with a Yanaco MP-S3 (Yanaco, Tokyo, Japan)and are uncorrected.

HPLC was performed using the YMC-Pack Silica or YMC-Pack Pro C18 columns and a Shodex RI-101 detector (Showa Denko K. K., Tokyo, Japan). ¹H-NMR spectra were recorded using a Varian Unity 500 (500-MHz) spectrometer (Varian Inc., Palo Alto, CA, USA). Chemical shifts are reported in ppm from tetramethylsilane, used as the internal references (CDCl₃: δ_H 7.26 ppm), with solvent resonance resulting from incomplete deuteration. ¹³C-NMR spectra were recorded using a Varian Unity 500 (125-MHz) spectrometer with complete proton decoupling (Varian Inc., Palo Alto, CA, USA). Chemical shifts are reported in ppm from tetramethylsilane with the solvent as the internal reference (CDCl₃: δ_C 77.26 ppm). High-resolution mass spectra (HRMS) were obtained with a JEOL JMS-700 spectrometer at the Korea Basic Science Institute (JEOL Ltd., Tokyo, Japan). The optical rotations were measured using a JASCO digital polarimeter (JASCO International Co. Ltd., Tokyo, Japan), using a 5-cm cell. IR spectra were recorded using a JASCO FT/IR-4100 (JASCO International Co. Ltd., Tokyo, Japan). UV spectra were obtained using a Shimadzu UV-1650PC spectrophotometer (Shimadzu Corporation, Kyoto, Japan).

Low-angle X-ray diffraction (XRD) investigation was carried out in the low-angle range (2θ = 0.5° to 6°) utilizing a Bruker AXN analyzer. N₂ sorption analysis was performed by using the Nova 4000e surface area instrument. Fourier transform infrared (FTIR; JASCO FTIR 4100) spectra with a frequency ranging from 4000 to 400 cm⁻¹, were recorded using the KBr pellet technique. The surface morphology was studied by scanning electron microscopy (SEM, S4800). Transmission electron microscopy (TEM) images were collected on a JEOL 2010 operating at an acceleration voltage of 200 kV. Scanning electron microscopy (SEM) images were recorded with a JEOL 6400 microscope operating at 20 kV. Thermogravimetric analysis (TGA) was performed on a Perkin-Elmer Pyris Diamond thermogravimetric analyzer with a heating rate of 10 °C/min under N₂ atm. Particle size and zeta potential measurements were performed on the Malvern Zetasizer Nano-ZS. UV-vis spectral analysis was performed using an Agilent Inc. UV-Vis spectrophotometer.