A Supramolecular Array of Fullerenes by Quadruple Hydrogen Bonding

Abstract

General remarks. All reagents and solvents were used as received or purified using standard procedures. [60]Fullerene (99.5%) was purchased from Southern Chemical Group, LLC and used without purification. All reactions were performed under a nitrogen atmosphere unless indicated otherwise. Flash chromatography was performed using Kieselgel Merck Type 9385 (230-400 mesh). Analytical thin layer chromatography (TLC) was performed using aluminum coated Merck Kieselgel 60 F254 plates. Melting points were determined with a Mettler FP1 melting point apparatus equipped with a Mettler FP2 microscope. H-NMR and C-NMR spectroscopy were performed on a Varian Unity Plus (500 MHz) instrument or on a Varian VXR-300 (300 MHz) instrument as indicated, at 298 K. Coupling constants (J) are denoted in Hz. Multiplicities are denoted as follows: s = singlet, d = doublet, t = triplet, q = quartet, p = pentet, dd = double doublet, m = multiplet, br = broad. FT-IR spectra were recorded on a Mattson Galaxy 4020 instrument. UV-Vis spectra were recorded on a Hewlett Packard HP 8452 UV-Vis spectrophotometer. High Resolution Mass Spectroscopy (HRMS) were performed on a JEOL JMS 600 spectrometer (positive ion EI mode). MALDI-TOF-MS measurements were performed on a Micromass TofSpec E apparatus (negative-ion reflector mode) by using elemental sulfur as a matrix (See: Brune, D. C. Rapid Commun. Mass Spectrom. 1999, 13, 384 389). Measurements were performed on aliquots of the analyte (1 mg/mL) and elemental sulfur (10 mg/mL) in CS2 or CHCl3. HPLC analyses were performed on a Hewlett Packard HP LC-Chemstation 3D (HP 1100 Series) using an analytical Cosmosil Buckyprep column (4.6 x 250 mm). Cyclic Voltammetry was performed using an Autolab PGStat 100. Elemental analysis were performed by the Microanalytical Department of this laboratory.