A cationic water-soluble pillar[5]arene: synthesis and host–guest complexation with sodium 1-octanesulfonate

Yingjie Ma, Xiaofan Ji, Fei Xiang, Xiaodong Chi, Chengyou Han, Jiuming He, Zeper Abliz, Weixiang Chen, Feihe Huang
2011 Chemical Communications  
S3 2. Synthesis of 1 Scheme S1. Synthesis of 1. Synthesis of compound 2 S1 Carbon tetrabromide (39.8 g, 120 mmol) was slowly added in small portions to a solution of 1,4-bis(2-hydroxyethoxy)benzene (10.0 g, 50.4 mmol) and triphenylphosphine (31.5 g, 120 mmol) in 300 mL of dry acetonitrile at 0 °C with stirring. The reaction mixture was allowed to warm to room temperature, and the resulting clear solution was stirred for another 4 h under N 2 . Then 200 mL of cold water was added to the reaction
more » ... mixture, where product 2 precipitated as a white solid. The product was collected by vacuum filtration, thoroughly washed with methanol/water 60:40, and then recrystalized from methanol. The white flake-like crystals were dried under high vacuum (13.8 g, 85 %). The 1 H NMR spectrum of 2 is shown in Figure S1 . 1 H NMR (400 MHz, chloroform-d, room temperature) δ (ppm): 6.89 (s, 4H), 4.27 (t, J = 6.3 Hz, 4H), 3.64 (t, J = 6.3 Hz, 4H). Electronic Supplementary Material (ESI) for Chemical Communications This journal is
doi:10.1039/c1cc15660h pmid:22011730 fatcat:f5fvercinjdz3eve7hjv7agh6a