Reagents, solvents, guest molecules, and synthetic precursors were purchased from commercial suppliers at ACS Reagent Grade or equivalent purity and used without further purification. Pyrogallol, butrylaldehyde, anthracene, fluoranthene, pyrene, and fluorene were obtained from Acros Organics. Hydrochloric acid, ethanol, and methanol were obtained from Fisher Scientific. Undecanal and 1,5-diaminonaphthalene were obtained from TCI. Carbazole and coumarin were obtained from Sigma-Aldrich. 1-Adamantanecarboxylic acid and [2.2]paracyclophane were obtained from Alfa Aesar and Combi-blocks respectively. Deuterated solvents for NMR spectroscopy were purchased from Cambridge Isotopes. CDCl3 was filtered through basic alumina prior to use. Pyrogallol[4]arenes 1a and 1b were synthesized using published procedures.26 ,32
1H and 13C solution NMR spectra were acquired using a Bruker Avance IIIHD 600 MHz, a Varian Unity INOVA 500 MHz, or a Varian Mercury 400 MHz spectrometer. Residual solvent peaks were used as internal standards: CHCl3 (δH = 7.26 ppm; δC = 77.16 ppm), benzene (δH = 7.16 ppm; δC = 128.06 ppm). NMR measurements performed in CCl4 used a coaxial NMR tube insert and C6D6 for an external solvent lock and chemical shift referencing.
1H and 13C solution NMR spectra were acquired using a Bruker Avance IIIHD 600 MHz, a Varian Unity INOVA 500 MHz, or a Varian Mercury 400 MHz spectrometer. Residual solvent peaks were used as internal standards: CHCl3 (δH = 7.26 ppm; δC = 77.16 ppm), benzene (δH = 7.16 ppm; δC = 128.06 ppm). NMR measurements performed in CCl4 used a coaxial NMR tube insert and C6D6 for an external solvent lock and chemical shift referencing.