Jnm la 300

6,6-bieckol (BK), dieckol (DK), phlorofucofuroeckol A (PFFA), phloroglucinol 6,6-bieckol (PGB), and 2,7-phyrogalyol-6,6-bieckol (2,7PGB) were isolated from Ecklonia cava; octaphlorethol A (OPA), diphlorethohydroxycarmalol (DPHC), saringosterol acetate (SA), and Apo9F were isolated from Ishige foliacea, Ishige okamura, Hizikia fusiformis, and Undariopsis peteseniana, respectively (Table 1). Structures of the listed compounds were determined using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS, Finnigan MAT, San Jose, CA, USA), infrared spectroscopy, and nuclear magnetic resonance (NMR, JEOL JNM-LA 300, Tokyo, Japan) spectroscopy, as we previously described [20 (link),21 (link),22 (link),23 (link)].

The molecular weights and PDI values were determined by gel permeation chromatography on a Shimadzu HPLC-8020 using a calibration curve based on polystyrene standards in CHCl₃ at 40°C. ¹H-NMR spectra were recorded on JEOL JNM-LA 300 or 400 MHz instruments using CDCl₃ or DMSO-d₆ as the solvent. MALDI-TOF-MS spectra were recorded on a Bruker Daltonics Ultraflex using dithranol as the matrix (10 mg ml⁻¹ in CHCl₃). UV–vis spectra were recorded on a JASCO V-650 spectrophotometer. XRD was performed by Rigaku Smart Lab. The incident angle for the in-plane measurements was 0.2°. 2D GIWAXS was measured on the BL19B2 and BL46XU beamlines at SPring-8 with an incident angle of 0.12°. The film samples were prepared by spin coating the polymer solution in CHCl₃ on the Si/SiO₂ (300 nm) substrate at 2500 r.p.m. for 60 s. The concentrations were 7 mg ml⁻¹, 9 mg ml⁻¹, 11 mg ml⁻¹, 12 mg ml⁻¹ and 15 mg ml⁻¹ for Si0, Si30, Si50, Si70 and Si100, respectively. Photoelectron spectroscopy in air was performed on a Riken Keiki AC-2 instrument. The solubility of the polymers was tested by weighing out approximately 10 mg of the samples into a vial and adding CHCl₃ by 50 µl incrementally until the complete dissolution of the polymer was observed by the naked eye.

¹H NMR spectra were recorded on a JNM-LA300 (JEOL) instrument (300 MHz for ¹H NMR) or JNM-LA400 instrument (400 MHz for ¹H NMR). Mass spectra (MS, ESI-TOF) were measured with a JMS-T100LC AccuTOF (JEOL). Absorption spectra were obtained with a UV-1650PC UV/Vis spectrometer (Shimadzu), and fluorescence spectra were obtained with a F4500 fluorescence spectrometer (Hitachi). LC-MS analysis were performed on a reverse-phase column (Inertsil C18, GL Sciences (Tokyo, Japan)), fitted on an Agilent Technologies 1200 series/6130 Quadrupole (LC/MS) system, using a linear gradient of eluent A (0.1% formic acid in H₂O) and eluent B (0.1% formic acid in 80% acetonitrile, 20% H₂O) (A/B: 95/5 to 5/95 in 17.5 min). Detected at 490 nm. All experiments were carried out at 298 K, unless otherwise specified.