Morpholine

Materials: 1-Acetylpyrene (Frinton labs, Hainesport, NJ, USA), morpholine (Alfa Aesar, Haverhill, MA, USA, +99%), sulfur, (Sigma Aldrich, St. Louis, MO, USA, reagent grade, purified by refining), p-toluene sulfonic acid, (Acros but distributed by Fisher Scientific: Pittsburgh, PA, USA; monohydrate), 20–25% aminopropylmethylsiloxane—dimethylsiloxane co-polymer (Gelest, Morrisville, PA, USA, AMS-1203; M_w: 20,000), acetic anhydride (Sigma, ≥99%), potassium bicarbonate (Sigma, 99%), 1,1′-carbonyldiimidazole (Fisher, Hampton, NH, USA, 97%, CDI) were used as received. N,N′-Dicyclohexylcarbodiimide (DCC) and N,N-dimethylpyridin-4-amine (DMAP) were purchased from Aldrich. Dichloromethane (Fisher, 99%) and dimethylsulfoxide (Fisher, 99%; DMSO) were dried over 4 Å molecular sieves for 3 days before use. Tetrahydrofuran (THF, Caledon, ON, Canada, distilled in glass), N,N-dimethylformamide (DMF, Sigma, ≥99.8), and dioxane (Sigma, ≥99.5%) were used for the fluorescence measurements.

Fmoc-protected amino acids were purchased from CEM Corporation, and Pepceuticals. N, N-Dimethylformamide (DMF) and diethyl ether (Et₂O) were purchased from Rathburn. Triisopropylsilane (TIPS), Trifluoroacetic acid (TFA), N, N-Diisopropylethylamine (DIPEA), N,N’-diisopropylcarbodiimide (DIC), ethyl cyano (hydroxyimino) acetate (Oxyma Pure), fluorescein-5-isothiocyanate (FITC), Fmoc-Lys(Alloc)-OH, Tetrakis(triphenylphosphine)palladium(0) {Pd(PPh₃)₄)}, and phenylsilane were purchased from Fluorochem. Morpholine was purchased from Alfa Aesar. Dichloromethane (DCM) was purchased from VWR. Acetonitrile (MeCN) was purchased from Honeywell. TentaGel S RAM resin was purchased from Rapp Polymere. All other reagents were purchased from Sigma Aldrich.