General Cyclooct-4-en-1-yl salen ligand monomer and the original mixture of macrocyclic salen ligands were synthesized following our previous report. 1 All reagents were obtained from commercial suppliers and, unless specified below, used without further purification. Dichloromethane was dried by passing through columns of activated copper and alumina successively. Chlorobenzene was distilled under argon prior to use. Flash column chromatography was performed using silica gel 60 Å (230-400

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... from Sorbent Technologies. Size-exclusive chromatography was performed using Toyopearl HW-40 SEC resin purchased from Sigma-Aldrich. 1 H NMR spectra were recorded at 25 °C on a Bruker AC 400 (400 MHz) spectrometer. 13 C NMR spectra were obtained at 100.0 MHz on a Bruker AC 400 spectrometer. All chemical shifts are reported in parts per million (ppm) with reference to solvent residual peaks. MALDI-TOF mass spectra were recorded on a Bruker OmniFLEX Maldi-TOF spectrometer using dithranol as the matrix. Gel-permeation chromatography (GPC) analyses were performed on a Shimadzu LC-10AD pump coupled to a UV detector. American Polymer Standards columns were used with THF as the mobile phase (flow rate at 1.0 mL/min) and poly(styrene)s were employed as standards for calibration. The chiral GC analyses were carried on a Shimadzu GC 14-A instrument equipped with an FID detector. Either a Chiraldex γ-TA column (Advanced Separation Technologies, Inc.) or a β-Dex 120 column (Supelco) was used with helium as the carrier gas. The chiral HPLC analyses were performed on a Shimadzu-10A Supplementary Material (ESI)